AI That Actually Works: Orchestrating Content, Context, and Workflows at Scale
BY Ade Akin June 09, 2026Grant Hoffman was trained as a sketch artist before he became an AI solutions architect, and the most valuable lesson he learned during that time had nothing to do with drawing the subject in front of him. “If you are trying to depict something and it never seems to come out right, you draw the negative space around it,” he said during a From Day One webinar. “I don’t draw the camera, I draw the space around the camera, and by doing so, I draw the camera, because my brain has no concept of what the space around the camera is supposed to look like.”Hofmann, now the AI solutions architect at Orange Logic, believes that lesson also applies to enterprise AI projects. Companies often point AI at the tasks it’s needed for, assuming the algorithm will figure out the rest, but the real work lies in mapping the invisible scaffolding around the task: brand rules, legal guardrails, and the tribal knowledge that only lives in the minds of a few seasoned employees. Without that layer of context, AI creates blur instead of drawing the camera.That insight formed the core of the webinar’s conversation. Hoffman was joined by his colleague Misti Vogt, the SVP of engagement at Orange Logic, to lay out a five-step path for moving AI solutions from experiment to infrastructure, grounded in their work with organizations entrusted with managing millions of digital assets. Why Most AI Projects DisappointGrant Hofmann, AI solutions architect at Orange Logic, spoke during the webinar (company photo)Hofmann says the biggest reason some AI initiatives fail is that companies treat AI as a magic bullet when it actually operates on the law of averages.“These foundation models that most of us are building with are built on billions of parameters that represent relationships between a training data set that is mostly a single sum of human knowledge,” he said. “That is an average, and if we’re making assumptions based on the average, we are not capturing the nuance of how you or your organization really think about how to do a task.”That nuance covers everything from tone of voice to rights management. “The way that I ask people to see it is as a magnifying glass,” Hofmann said. “If your process is good and it’s well thought out and it’s well documented, adding a little bit of AI to the mix is going to make it look 10 times more successful. But if your process is shaky, or if it relies on a lot of tribal knowledge, that’s where your hidden 10x can go the opposite direction.” Hofmann called these friction points “qualitative bottlenecks,” tasks where human intuition has always helped create the path. Vogt highlighted the foundational challenge organizations face when creating AI workflows: “The machines can’t be expected to know your brand rules, the governance for your brand, your voice, your rights, your taxonomy. So you have to create an ecosystem and infrastructure where they can easily lean into that information and get what they need when they need it.”Vogt now calls this “enterprise content infrastructure.” Orange Logic has been building such platforms since 1998, and the company was recognized as a Leader by both Gartner and Forrester in 2025, she says.From Record to RevenueVogt described a fundamental shift in content platforms. “Digital asset management has moved from really a system of record into a system of action, which puts us a lot closer to the revenue side of the business,” she said. “What you can do today is start benchmarking, because what’s happening for our customers who are starting to deploy these agents? It doesn’t translate really well, because they didn’t benchmark on the former process.”Hofmann recommends identifying metrics that tie back to dollar-value outcomes: increased output, reduced legal review times, and lower tool bloat. “Cool factor doesn’t really hold water with the guy that signs the checks,” he added. “Before we fully get started, as we are in that scoping stage, we identify the metrics that we want to use in order to report, like, hey, this was really successful.” That discipline also prevents scope creep. “Being able to point to your metric for every new idea and say, 'How is this going to influence my metrics that I’m using to report value?’ Is this a good way to keep things on track?”Teaching Machines Your RulesHofmann offered a low-tech exercise called the “sticky note method” to teach how to extract tribal knowledge within an organization. “Start with a pile of sticky notes next to you. Whether it’s you or whether you’re sitting down with your expert, we watch them, or we do the task ourselves. Every time our eyes start shifting to a different part of the screen, every time we consult a piece of prior knowledge, every single little piece of that gets documented by writing it down on the sticky note.” By the time the task is completed, the team has produced the first drafts of prompts and workflows, while highlighting steps that need a human touch. The method echoes some of the lessons Hofmann learned during his art training. “That sort of assumption engine that makes my day-to-day so fast and easy can get in my way or kill my accuracy,” he said. Vogt agreed: “It forces you out of common thinking. It’s not just fitting AI into current business processes; it’s rethinking the business processes.”Crawl, Walk, RunHofmann and Vogt advocate for a phased approach to AI adoption that unfolds in three stages. The first, "crawl," focuses on using AI as a supportive tool, offering suggestions while humans guide and refine every action. In the "walk" phase, organizations introduce greater rigor by automating complete handoffs between steps and establishing clear benchmarks that make it easier to detect model drift, the point at which AI performance begins to decline. The final stage, "run," is reached when the system has been refined enough to consistently produce the desired output with minimal intervention.Hofmann says that remaining in the crawl or walk phase is perfectly acceptable. “Run is a place that’s earned, not assumed.” Both speakers emphasized the importance of people remaining at the forefront of all AI processes. “Focus on people,” Hofmann said. “It’s not a replacement for humans; it should be an elevator for them.” Vogt recalled telling an employee who feared automation, “If you are able to automate your entire job with agents, you will become the most valuable employee that we have. So, go for it, push the limits, challenge it, test it.”Hofmann ended the conversation with measured optimism. “The bad news is it’s harder than everyone thought it was going to be, but the good news is it’s also way easier than I think we think it is,” he said. “What I find is that AI projects are sort of this cascading explosion of success. It does not take a very long amount of time to go from our first successful AI project to starting to build an operating system that encompasses and enshrouds our business.” The secret to the success Hofmann has enjoyed is doing the human work first, drawing the negative space before you start drawing the camera. Editor’s note: From Day One thanks our partner, Orange Logic, for sponsoring this webinar. Ade Akin covers artificial intelligence, workplace wellness, HR trends, and digital health solutions.(Photo by imaginima/iStock)
Activate Your Human Edge: Leading Brain-Friendly Change in the Age of AI
BY Kristen Kwiatkowski June 04, 2026Recently, a student showed Dossier Harps her resume, saying it was completed using AI. Harps was impressed by the overall inclusions in the resume but noted one serious mistake. In the summary section, the student was said to have 20 years of experience. The problem? The student was only 20 years old. During a thought leadership spotlight at From Day One’s Minneapolis conference, Harps, facilitation manager at LifeLabs Learning, illustrated this story as an example as to how AI needs oversight and guidance for a variety of tasks. “Moments like this remind us that, while AI is powerful, humans still need discernment,” said Harps. “Humans still need judgment, humans still need coaching, and humans still need each other.”Harps also described a recent experience where she was in a pharmacy and customers waiting in a long line started to express discontent with the employees handling the checkout procedure. This made her think of incivility in the workplace, which has increased since 2020. This may be due to many individuals experiencing more stress, uncertainty, and emotional exhaustion which in turn can lead to empathy and patience eroding, says Harps. “So, when people ask me in my work, am I scared of AI, my answer is no,” said Harps. “I am not nervous about AI, I am nervous about incivility.”However, AI can cause discomfort and uncertainty for many individuals. For example, employees who have been doing their job for years without the help of AI and ultimately have to start using AI may feel discomfort and be unsure as to the direction they’re headed. “It could feel really scary, because when the way that we work changes, our sense of confidence, control, and our competence can get disrupted,” she said. Dossier Harps, facilitation manager at LifeLabs Learning, led the thought leadership spotlight in MinneapolisHarps discussed a concept offered by Robert Katz, a leadership researcher, which is a three skills approach to effective leadership which includes technical skills, human skills, and conceptual skills. Technical skills are what you know how to do, human skills are how you work with people, and conceptual skills are how you think strategically. Many organizations are focusing on technical AI skills, which are important, however, there needs to be more focus on human skills and conceptual skills and how they pertain to AI, she says. “We have to have the human skills, such as communicating influentially, understanding how different people learn and process, giving feedback, having courageous conversations when you notice emotional stress or incivility in your teams, building psychological safety and coaching people through uncertainty,” said Harps. “And conceptual skills are about seeing the bigger picture, like pattern recognition, systems thinking, and change implementation,” she continued.As with the seven stages of grief, an adaptation of Elisabeth Kübler-Ross’s five stages of grief, this concept can also apply in similar form to workplace change. Not everyone will be within the same stage and individuals in the workplace may be in different generations, have different ways of learning, and different experiences with technology. Trust is also a major component for organizations to consider. “Companies forget to acknowledge the emotions that build or break trust,” said Harps. “The major tenants of trust are credibility, reliability, and psychological safety and trust becomes especially important during times of uncertainty and change.”The first component of trust is credibility, and individuals want to know if the leader is competent to lead them through change. Next is reliability and can you depend on that person. In addition, psychological safety is also important with trust and individuals want to be able to ask questions and be honest with the leaders in their organizations. “So, once we understand the emotional side of change and the importance of trust, the next question is how do leaders practice this in real life?” said Harps.Being a great leader isn’t just about being a good person and that’s all. A great leader has to be intentional, deliberate, and exhibit mindful behaviors and actions. “Great leadership happens on purpose,” she said.Harps describes a model they teach at LifeLabs Learning called CAMPS, which is based on the concept that the brain constantly scans for threats or rewards. Under the CAMPS model, the features include certainty, autonomy, meaning, progress, and social inclusion. “What I love about this framework is that it reminds us that understanding and addressing the human experience is the greatest differentiator in the age of AI,” said Harps. As individuals navigate AI and uncover how this technology will evolve in the years that follow, keeping one factor in mind along the way is essential. “I do believe that the most underrated leadership skill in the age of AI is the ability to inspire hope.”“People are searching for something deeply human to hold on to, which is truth and hope,” continued Harps. “The truth is things are changing, and things will continue to change, and we have to evolve and change with the times to be prepared for the future of work, but hope says we can learn, we can adapt, we can grow, we can move forward, and that is the real human edge in the age of AI. It’s not just mastering the new technology, but leading people through uncertainty and confusion with compassion, trust, and hope.”Editor’s note: From Day One thanks our partner, LifeLabs Learning, for sponsoring this thought leadership spotlight.Kristen Kwiatkowski is a professional freelance writer covering a wide array of industries, with a focus on food and beverage and business. Her work has been featured in the Bucks County Herald, Eater Philly, Edible Lehigh Valley, Cider Culture, and The Town Dish. (Photos by Josh Larson for From Day One)
Translating Global Strategy Into Local Impact
BY Emily McCrary-Ruiz-Esparza June 03, 2026There’s too much lag between strategy and execution of global campaigns, says Kelly Heilpern, chief strategy officer at Ammunition. Organizations can spend months, or even a year, developing a global strategy based on timely data that’s stale by the time campaigns roll out.“The brands getting it right,” she said, “are the ones who have figured out how to make those decisions faster, without sacrificing strategic integrity,” and that requires collaboration and trust: among marketing, sales, and the agency partner. The challenge is that truly global campaigns require some degree of tailoring to local markets, and effective localization cannot be handed down from on high. Quick decisions have to be made, with local input. During a From Day One webinar on translating global strategy into local impact, Heilpern and her colleagues discussed how they designed and tested a campaign for one of the world’s largest building products manufacturers across five new markets with unique concerns. Bringing DensDeck to EuropeGeorgia Pacific was ready to bring a stalwart product to a new market.DensDeck, a roofboard that acts as a fire-resistant thermal barrier, is common across North America—it’s in everything from “airports to stadiums, hotels, and high rises,” said Mallory Faust, the director of brand strategy for Georgia-Pacific Building Products—but it’s relatively new in Europe. Leaders from Ammunition spoke about "Translating Global Strategy Into Local Impact" (photo by From Day One)Expansion of solar rooftops and data center construction has developers focused on resilience in building design, “putting more pressure on roofing systems to perform better and be more durable,” and opening a huge market opportunity for Georgia Pacific, she says. They chose five geographies: the Netherlands, Germany, Belgium, the UK, and Spain. The challenge for Faust is not just introducing a new product within an existing category, “we’re trying to establish the category,” which meant they had to start with education. “We realized pretty quickly that we couldn’t take a North American approach and just drop it into Europe.”Barriers to adoption vary widely by market: Some buyers need technical proof of performance while others are more price sensitive or prefer a reference from someone they trust. So Georgia Pacific and the Ammunition team brought in local stakeholders “from the outset, so they feel like they have ownership and autonomy,” said Renaye Edwards, Ammunition’s global COO and managing director.They gathered a coalition across product, technical, and regional teams for a weeklong intensive planning session. “A lot of different perspectives went into identifying where the opportunities existed, as well as what the barriers to adoption would be within each market,” Faust said.Right away, the collaboration paid off. The first strategy for the UK market was a “Mind the Gap” campaign—the idea being that DensDeck could close the quality “gap” in roofing systems. But in sales conversations, the tagline was being interpreted as not falling through physical gaps during installation. “Testing is such an important part of the process,” Heilpern said. “That would have been a huge miss for us to deploy this campaign that didn’t connect the way we intended it to.”Pitfalls of Localization, and How to Avoid ThemBut how local is too local? After all, time is of the essence. “The overall positioning really shouldn’t change what DensDeck is: a solution that helps protect the contents inside of a building and extend the life of a roof,” said Faust. “But global consistency doesn’t mean that every market should operate the exact same way.”Some tweaks are simple: Images also have to be localized since roofs in Spain look very different than roofs in the Netherlands. Others require a little more research, like which small proof points to play up—mitigating fire risk might perform better in one area while longevity will perform better in another. Localization also costs money, which isn’t always abundant. If the budget is slim, don’t roll it out in every market at once, Edwards said, but “identify those markets where you have the right to win” and you’re past the education stage with your market. “Once you’ve done that,” she added, “you can test and learn very quickly,” proving your strategy before going back to the business for more funds.Winning requires differentiation, which is often made through an emotional appeal. Easier said than done for roofboard, but by no means impossible, said Heilpern. “[Builders] are accountable for the performance of their roof. We can speak to them as consumers who are making very important decisions and make them feel seen, make them feel heard, and make them feel like there’s a product that solves a problem that keeps them up at night.”Editor’s note: From Day One thanks our partner, Ammunition, for sponsoring this thought leadership spotlight. Emily McCrary-Ruiz-Esparza is an independent journalist and From Day One contributing editor who writes about business and the world of work. Her work has appeared in the Economist, the BBC, The Washington Post, Inc., and Business Insider, among others. She is the recipient of a Virginia Press Association award for business and financial journalism. She is the host of How to Be Anything, the podcast about people with unusual jobs.(Photo by Cecilie_Arcurs/iStock)
Turning Executive Potential into Measurable Performance
BY Emily McCrary-Ruiz-Esparza June 01, 2026It’s a common mistake to place the weight of an executive hiring decision on the interview, says Bert Hensley, the CEO of executive search firm Morgan Samuels.Interviewing isn’t inherently wrong, but it is overvalued, he shared during a From Day One webinar on executive recruitment. Naturally, we tend to favor people who resemble us in background, philosophy, working style, and that’s what interviews often reveal, but the C-suite doesn’t benefit from homogeneity. Companies would be well advised to pause and look backward, at the candidate’s career, and forward, at the candidate’s potential.But we’re getting ahead of ourselves. Even before candidates are brought in, the hiring team must be in agreement on what success looks like—in great detail, Hensley says. A CFO candidate must have acquisition experience, sure. But how many deals? Of what size? And in what geographies? And on top of that, when they get to your company, what should they be prepared to accomplish? “Be crystal clear on the specific things this human being has got to get done in the next 24 months for us to say, ‘Wow, they were a great success.’”Bert Hensley, chairman and CEO of Morgan Samuels Company, pictured, spoke with journalist Emily McCrary-Ruiz-Esparza during the webinar (company photo)This becomes a scorecard everyone on the hiring team will use. “Otherwise, you’ll end up hiring people that are eminently well qualified for what they’ve done, but not necessarily what you need,” he said.Candidate evaluation begins with a retrospective look at their career, asking “not just what they’ve done, but how they’ve done it,” Hensley said. And anything on their resume is fair game. He goes back as many as 10 or 15 years to probe at how a candidate reduced turnover or cut costs, asking, “how did you think through the problem? Give me the framework of analysis that you used. What data told you this was a problem?”Unique to the process at Morgan Samuels is the written self-assessment, which was born from an unusual request many years ago. The vice chair of a global banking company asked Hensley to subject candidates to a lengthy, written self-assessment of their accomplishments. Hensley assumed the request would never fly among those making upwards of $2 million per year and working 100-hour weeks. “I was completely shocked at how easy it was to get the candidates to do it,” he said.The self-assessment helps companies avoid arrogant candidates, “which is really just a cover for extreme insecurity,” Hensley said, and can hurt a company. Arrogant people are more likely to conceal problems or fail to disseminate information that should go around, and “if you get a self assessment back and it says, ‘I did this, I did that, I did this,’” then you’re not looking at a team player. “The best leaders are those who talk in terms of ‘we.’”When it’s time to look forward, candidates are handed a real problem to solve using real company financials (under an NDA, of course). The transparency and the accountability benefit both sides. Candidates can’t later plead ignorance about a debt problem or a customer retention issue, and they can start planning their first actions in the role, being very frank about the resources they need.You may be surprised who wobbles at this stage. Hensley said he’s seen heavily credentialed candidates with enviable pedigrees request millions of dollars to build teams “without any proof of concept of how he would gradually grow the sales team.” They ask for blank checks, but won’t bother to make a plan for using the cash. This is what Hensley calls a “presider,” who simply issues orders from a distance. “We’re always looking for world-class operators who will roll up their sleeves and get stuff done.” Executives often fail because they’re not suited to the company culture, he said. It’s worth it to take the time to assess their working style, their leadership style, and even their emotional makeup. “Are they a drill sergeant just barking orders, or are they going to be collaborative? Are they going to inspire your workforce and collaborate with the team?”It’s easy to overvalue great performance in the interview, or even a big stumble, but “your entire decision should not be based on one score. We’re talking about human beings, who are very complex.”Editor’s note: From Day One thanks our partner, Morgan Samuels Company, for sponsoring this webinar. Emily McCrary-Ruiz-Esparza is an independent journalist and From Day One contributing editor who writes about business and the world of work. Her work has appeared in the Economist, the BBC, The Washington Post, Inc., and Business Insider, among others. She is the recipient of a Virginia Press Association award for business and financial journalism. She is the host of How to Be Anything, the podcast about people with unusual jobs.(Photo by milorad kravic/iStock)
Why Delegation Breaks Down and What It Takes to Build Accountability at Scale
BY Kristen Kwiatkowski May 28, 2026Delegation sits at the center of how managers create clarity, ownership, and accountability in the flow of work. It’s vital that leaders know how to delegate tasks to their team members and do so as often as possible.Kelli Wingo, facilitator at ThinkHuman, shared how to build accountability on the frontline teams by delegating effectively during a thought leadership spotlight at From Day One’s May virtual conference.It’s not uncommon for people to take on tasks they should have delegated, only to have those tasks take longer than expected. As they work through them, they often find themselves thinking about other, more valuable ways they could be spending their time. “As you are learning how to better support and develop frontline workforce and tools, training, investment, and engagement are all great, so keep doing them,” said Wingo. “But tools, training, investment and engagement are only effective if they are in service to how a leader can create accountability in the flow of work.”There are three key things that delegation makes possible for you as a leader. First, you as a leader create a vision for the team. “The second thing is to orchestrate a team that is successful and empowered in achieving its goals,” said Wingo. “When we’re doing what we’re capable of doing, that is so much greater than just doing what we’re told to do,” said Wingo. The third key benefit of delegation is that it enables your team to do more with less.What Prevents Leaders From Delegating?Kelli Wingo, facilitator at ThinkHuman, led the virtual session about delegation and accountability (company photo)Most of us understand the mechanics of delegation and accountability, so what’s holding us back? There are some blocks that prevent individuals from delegating. Some leaders feel they can do the task better themselves. Wingo shared how this mindset can be overcome.“One way of looking at this is it’s an opportunity for growth or care, to invest in your team members,” said Wingo. “If your team members see that you are really invested in their growth, their professional growth, getting them into their stretch zone, then a certain level of respect comes from that,” said Wingo.When leaders want all the shine and recognition, they can begin to see their team’s successes as their own, said Wingo. This is where the leader steps into a coach role and helps their team grow. Leaders also may resist admitting they are wrong, which can become a barrier to effective delegation. This comes back to the importance of responsibility and accountability. Acknowledging and understanding these blocks can help us with a mindset shift. “So we want to go from I can do it faster and better myself, to my job is to help the people around me rise,” said Wingo.The Delegation ProcessThere are a few steps in the delegation process. First, clarify the task that needs to be completed. From a longer list, narrow it down to the top three to five tasks to delegate. As a leader, your role is to set the vision and have your team execute. Next, decide who on your team should own each task. It’s also important to step back and assess whether all tasks are truly necessary or if some have continued simply out of habit or routine.And once you delegate tasks to your team, you don’t want to just hand off the task list and then leave it at that. You want to have specific timelines, check-ins, and other safeguards in place to ensure that your team members execute each task in a proper, timely manner. Editor’s note: From Day One thanks our partner, ThinkHuman, for sponsoring this thought leadership spotlight. Kristen Kwiatkowski is a professional freelance writer covering a wide array of industries, with a focus on food and beverage and business. Her work has been featured in the Bucks County Herald, Eater Philly, Edible Lehigh Valley, Cider Culture, and The Town Dish.(Photo by Cecilie_Arcurs/iStock)
From Advice to Action: How Financial Coaching Drives Impact For Employers
BY Ade Akin May 27, 2026Many of the employees Greg Palmeri talks to have already suffered in silence for years before calling him. “A lot of times people will come to us when their financial situation is so bad that it’s almost too hard to fix,” Palmieri, a senior manager of financial planning at SoFi, said. “You wish you had talked to them a year ago, before they made that big financial decision.” That all-too-common moment of crisis illuminates a yawning gap in workplace benefits. According to WTW’s Global Benefits Attitude Survey, 66% of employees say they want more financial well-being support from their employer, yet only 23% of companies are currently providing it. During a conversation at a From Day One webinar titled “From Advice to Action: How Financial Coaching Drives Impact For Employers,” Palmieri and his colleague, Trevor Smith, SoFi’s business development director, explored how personalized financial coaching can bridge that 43-point gap, moving employees from reactive panic to proactive planning and giving employers a measurable stake in their people’s financial health. The Front Lines of Financial AnxietyWith nearly two decades of experience, Greg Palmieri hears firsthand the financial anxieties employees carry into coaching conversations, often long after the stress has taken root. The questions, he says, shift with economic cycles but often circle back to the same core anxieties.Greg Palmieri, senior manager of financial planning at SoFi, spoke during the webinar (company photo)“When we were in the pandemic era, a lot of people had more time on their hands, and they were more detail-oriented about their finances and wanted a more complex view,” Palmieri said. “Now I find that a lot more people are dealing with debt and trying to juggle that debt—what’s the best way to pay it down? Should they be saving for retirement while paying down debt?”Palmieri says the triggers that prompt employees to finally book an appointment with a financial coach are almost always reactive rather than proactive. A job change, a home purchase, a new child. He notes that people often seek planners “when their financial situation is so bad that it’s almost too hard to fix.” He often wishes they had sought his help earlier. “A lot of people will come to us after the fact. They didn’t really know they could even talk to someone before some of these big financial decisions,” Palmieri added. Three Personas, One ApproachPalmieri described three broad personas that often emerge on planning calls: the worrier, the juggler, and the optimizer. The worrier struggles to make it to their next paycheck. The juggler manages competing priorities, such as student loans, equity compensation, and saving for a home, and does reasonably well, but lacks clarity on what to tackle first. The optimizer has the resources but needs help refining their strategy, particularly around tax-efficient retirement planning.Despite these differences, Palmieri’s approach begins the same way. “The first question I’m really going to ask someone is, what are they looking to accomplish from that call?” he said. “I like to come in with an open mind and try to understand. Basically, people have no clue what they want to accomplish, which is perfectly fine.”That investigative conversation, asking about goals, then about the data behind them, is what Palmieri views as the real craft of financial planning. “Everyone can kind of Google search it, but trying to understand, does this person know their finances? How do they think about money? Tailoring that advice to that person is what separates a good planner from an exceptional planner,” he said. Accountability Over a Sales PitchA recurring concern Smith hears from HR leaders is whether financial planning benefits are simply a vehicle for product sales. SoFi’s model, he emphasizes, is built differently. Planners carry no sales quotas. Their performance scorecard is based on three metrics: appointment availability (50%), Net Promoter Score (30%), and compliance with regulatory standards (20%). “There are no sales goals or anything,” Palmieri said. “They’re 100% salary. They get a bonus, but that bonus is tied to how well SoFi does, not how many products they sell.” This framework appears to be working, says Palmieri. The show rate for scheduled appointments has climbed from roughly 60% in the early years to 80% today, and 25% of all calls are from returning members. “Some people don’t necessarily have a complicated situation. It’s a budgeting or a debt thing, and they want to be held accountable,” Palmieri said. “They want someone to talk to, a nonjudgmental person, understanding, like, hey, your debt was at $8,000 last time we spoke, you’re doing good, you’re at $6,000. Or, wait a second, now we’re at $10,000. What’s going on here?”The Human Element in a Digital AgeDigital tools now handle the first wave of financial curiosity. Smith sees a pattern where younger employees often start their financial planning journey with budgeting apps or AI chats, and eventually graduate to a live planner when they need the high-touch, one-on-one conversations they can’t get from a screen.“AI is an interesting point. I actually help train AI models here at SoFi,” Palmieri said. “But it’s still hard to get actual financial advice. It coaches you, it educates you. What I think a lot of people want is, ‘What should I do?’ They want specific [advice]: pay $5,000 toward your credit card debt, keep $10,000 in savings, contribute 10% toward your 401(k). All the frameworks are online. They want to know exactly what to do and walk away with it.”To address HR leaders weighing the benefits of investing in employee financial wellness, Smith points to a Consumer Financial Protection Bureau finding that such programs can deliver a three-to-one return on investment by reducing stress-related absenteeism and productivity loss. He says the immediate business case lies in the 43-point gap between what employees want and what most companies currently offer. “This is against the backdrop where 88% of folks are worried about basic living expenses, and employees with financial stress are twice as likely to be job searching.”When Greg Palmieri thinks about the return on his work, he doesn’t measure it in balance sheets. He thinks about one member who found her way out of nearly $50,000 in credit card debt, got on track for retirement, and recently bought a home in the Bay Area. “She just says, ‘I couldn’t do that without you,’” Palmieri said. “I can only be there as a sounding board. They’re doing the hard stuff.”Editor’s note: From Day One thanks our partner, SoFi, for sponsoring this webinar.Ade Akin covers artificial intelligence, workplace wellness, HR trends, and digital health solutions.(Photo by CHUBU/iStock)
The Hidden Driver of Frontline Retention: Why Caregiving Support Is the Benefit You’re Missing
BY Jessica Swenson May 20, 2026Sometimes, the hardest parts of your employees’ lives are the most invisible, especially for frontline workers. The variety of caregiving demands experienced by workers can have emotional, mental, financial, and physical tolls that aren’t visible to their employers, says Griffen Kelly, senior director of partnership development at Cariloop.By learning about and meeting the caregiving needs of their employees, he says, companies have the opportunity to elevate workplace culture while boosting employee loyalty and trust. “We’ve seen a shift from caregiving being a social need to being an economic need from an employer perspective,” Kelly said during a thought leadership spotlight at From Day One’s May virtual conference.The care economy is in crisis, he says. Forty-eight states are already reporting care shortages, and Americans over 65 are expected to soon outnumber those under 18 for the first time ever, causing demand to continue to grow faster than supply. Added to the already increasing demand for child care, this contributes to rapidly rising costs, long waitlists, and complex systems to navigate. According to Kelly, caregivers often spend an estimated average of 27 to 40 unpaid hours per week coordinating logistics, providers, and schedules.Still, these challenges can hide within organizations, and Kelly believes there are two key reasons. One is that many people don’t identify themselves as a caregiver because they feel they’re simply doing what is expected to meet family or social obligations. Griffen Kelly, senior director of partnership development at Cariloop, led the virtual thought leadership spotlight (company photo)The other possible reason is that people consciously avoid disclosing their care demands to avoid potential professional consequences. “There’s a certain stigma that can be associated with caregivers,” he said. “If I raise my hand and say I’m taking care of somebody, that might get me looked at differently at work. I might get passed up for that promotion because maybe I have too much on my plate and my manager is worried about my workload,” he said. Employee caregiving challenges often show up in the workplace through absenteeism, staffing instability, leave issues, and turnover. “For the most part, caregiving is reactionary,” said Kelly. “Typically, when you’re choosing between work and life, life is going to win out.” However, trying to balance work and caregiving with no support can lead to employee burnout, distraction, and retention issues. There is hope, says Kelly, especially if employers offer care support. Citing data provided by Cariloop, he states that over 75% of working parents are more likely to stay with employers offering care benefits, there can be significant reduction in unplanned absences, and many supported caregivers report improved productivity. Providing even modest caregiving support programs shows employees that you understand their struggles and demonstrates that they are supported by leadership. This not only helps them fulfill their responsibilities outside of work but drives workplace productivity.“Folks who do offer care benefits, however small, recognize that that is creating a culture of care from the top down. You’re showing that progression. You’re showing that buy-in from a leadership perspective,” he said. Cariloop sees a human-centered support model as “absolutely mission critical.” While digital tools are great for self-service, tracking of logistics, and broader needs, there is no replacement for one-on-one human relationships, personalized guidance, and emotional support.Their program focuses on direct coaching and caregiving advocacy to help families navigate an increasingly complicated caregiving landscape, including locating childcare services, making eldercare decisions, and long-term planning. It also offers backup solutions for immediate or near-term needs like emergency nanny coverage or temporary care support during crises. “Being able to offer flexible backup care is something that we have seen is a resounding need in the market,” said Kelly.The company’s approach also balances the needs of three key stakeholders—employers, employees, and care providers—by creating a more sustainable care ecosystem that includes flexibility and provider engagement.So, how can employers begin to implement a caregiving benefit program? Kelly recommends starting with your typical pulse surveys or other employee surveys. Be curious and ask questions to understand the unique and diverse needs of your teams. To evaluate potential ROI, he suggests aligning those metrics with employer priorities like utilization rates, improved return-to-work outcomes, reduced absenteeism, and better productivity. Kelly acknowledges that this type of support can be overlooked during benefits planning discussions, but encourages leaders that already offer the benefit to review utilization data, measure effectiveness, and seek opportunities to improve the value and engagement in your program.“There’s a lot of opportunity to drive a more valuable and sought-after benefit. Take a look under the hood, if you’re offering one of those benefits today, and see where maybe you can make some adjustments, where you can drive a more valuable benefit for your workforce.” He also emphasized the importance of meeting employees where they are and communicating effectively so they know what is available to them. By visibly and clearly demonstrating your investment in their support, you can strengthen employee confidence and dedication.“Our goal is always to make sure that we’re meeting employees in whatever way, shape or form is most conducive to them and their familial situation,” he said. “If you show that you’re invested in your employees and their caregiving needs, they will feel loyal and they will feel trusting in you as an employer.”Editor’s note: From Day One thanks our partner, Cariloop, for sponsoring this thought leadership spotlight. Jessica Swenson is a freelance writer and proofreader based in the Midwest. Learn more about her at jmswensonllc.com.(Photo by SeizaVisuals/iStock)
Blow Your System Up—Optimistically
BY Kristen Kwiatkowski May 19, 2026AI resistance isn't always about the tool, it’s about what the tool touches. Work is personal. Your accomplishments reflect real effort and real problem-solving. When AI enters the picture, people worry that what they built, and how they built it, might no longer matter.“That work means something,” said Rebecca Warren, senior director, talent centered transformation, at Eightfold, during a thought leadership spotlight at From Day One’s Live Seattle conference.It’s a fear a lot of people share: if AI can do my job, what does that mean for me? But the real truth is that the work moved. The skills didn’t disappear, but they in fact became foundational and moved underneath the AI strategy, says Warren. “AI shows up and it gets the credit or it gets the blame,” said Warren.Rebecca Warren, senior director of talent centered transformation at Eightfold, led the session “We say we want transformation, but then we defend the exact shape of the work that created the problems we’re trying to solve,” Warren said. “AI is not the transformation. It’s the moment of truth for whether your organization is actually built to, and ready to, transform, she says. Warren shared a “don’t pave cowpaths” example. Cows follow the same paths by habit and not because it’s the best route. Someone eventually comes along and paves the road that was traveled by habit. As a result, the bad route is permanent. “That’s what a lot of organizations are doing with AI,” said Warren. “They’re taking messy workflows, too many approvals, broken handoffs, duplicated work, and unnecessary meetings, and instead of asking, ‘Should they exist at all?’ they ask, ‘How do we automate it?’ ‘How do we make it faster?’ We just paved the cowpath. Faster wrong is still wrong.”“AI needs to force the question, ‘Why are we doing it this way?’” said Warren. “Don’t pave cowpaths, redesign the terrain.” Transformation is about what work survives. “Not everything is broken and not everything new is better, but the key is knowing the difference,” Warren said. It’s important to know when AI should be part of the conversation and when a human component is needed. For example, AI can handle administrative tasks, but there are times when human decision-making is essential, especially when ethics, trust, and nuance are involved. That’s where human judgment truly matters.In order for trust to occur, transparency must be present. People have to understand what’s changing and why. Without this, people build assumptions. “That’s why this is hard, and honestly, that’s good,” said Warren. “It should be hard because we’re not talking about buying a piece of software, we’re talking about redesigning how work moves, what people do, where to partner with AI, and what to change. That should feel heavy, that should slow you down, because sometimes the fastest way forward is to stop and ask what would need to be true for this to actually work.”It’s important to “slow down, build the guardrails, build the infrastructure, clarify the decision rights, and then move fast, not because caution is weakness, but because speed without design is just faster chaos,” said Warren.Editor’s note: From Day One thanks our partner, Eightfold, for sponsoring this thought leadership spotlight. Kristen Kwiatkowski is a professional freelance writer covering a wide array of industries, with a focus on food and beverage and business. Her work has been featured in the Bucks County Herald, Eater Philly, Edible Lehigh Valley, Cider Culture, and The Town Dish. (Photos by Josh Larson for From Day One)
Business Acumen for Sales Success: How Top Sellers Earn Executive Trust and Win Complex Deals
BY Ade Akin May 14, 2026Strong client relationships start with understanding what matters most to the customer and being able to clearly connect your solution to their business goals. “85% of business buyers are more likely to see you as a partner if you understand where their goals are, where their priorities are,” said Ben Cook, the president of Acumen Learning. He continued, “64% of reps don’t actually understand the industry of the customers they’re in, and by some estimates, 80% of salespeople cannot link their price and solution to the value they create for the client.”That gap between what executives want to hear and what most sellers actually say was the topic of a From Day One webinar led by Cook and Kevin Cope, the founder and CEO of Acumen Learning. Drawing on more than two decades of experience working with organizations, including 34 of the Fortune 50, they outlined a mental framework they call the Five Business Drivers. Their core argument is that business acumen provides the missing layer beneath every sales methodology, and without it, even the most diligent sellers stall out at the executive level.The Missing Layer Beneath Every MethodologyCope notes the leading sales methodologies: challenger sale, solution selling, and SPIN Selling (situation, problem, implication, and need-payoff questions). Among them, all assume sellers already possess deep business acumen. The challenger sale, he says, presumes “great sellers have a deep understanding of the customer’s business.” SPIN selling asks reps “to help the buyer quantify the cost of their problem and the value of their solution in terms of hard dollars.” Cope and Cook have learned something that contradicts these methodologies after spending over 24 years delivering business-acumen training across 40 countries, training over half a million people. “As you go up in organizations and get to more senior levels, the gap in business acumen is surprisingly big,” Cope said. “People are experts in their role or their function, whether it’s IT, operations, or marketing, but when it comes to understanding how they impact business—that gap is big.”That gap turns into lost deals. “It’s very easy and natural to lean into ‘this is the product I have, this is how it’s differentiated from my competition,’” Cook said. “A lot of times that conversation around product and solution is where most stay, feeling like that’s a story that wins.” But that’s not always the case. What Executives Actually Care About“Executives actually don’t care about your product,” Cook said. “What they really do care about is how you help them solve real-world business problems that they themselves are dealing with right now.” Those problems manifest as questions about operating leverage, profitable growth, efficiency, scale, and return on investment. “Their owners or shareholders are really looking for that, and just talking about the product obviously really misses what that story is.”Kevin Cope and Ben Cook of Acumen Learning led the webinar (photo by From Day One)The result is a gap between the seller and the buyer’s world that no amount of hard work can close. “You can work really, really hard and still feel irrelevant and disconnected from the things the person on the other side of the table really cares about,” Cook said. Executives want sellers who can answer two vital questions: What is the business problem this customer is trying to solve, and how does what I bring to the table specifically align with that problem? That’s what drives sales at the executive level. The Five Drivers That Shape Executive Thinking To bridge that gap, Cope introduced a mental model that he calls “an MBA in five words.” Every publicly traded company reports against the first three in its quarterly financial statements: the statement of cash flows, the income statement, and the balance sheet. He walked the audience through each driver in his model:Cash“If a company runs out of cash, they have two options. They either figure out a way to get more cash, or they go out of business,” Cope said. He used the now-defunct Sears as an example. Once the largest retailer in the world, representing 1% of U.S. GDP, Sears declared bankruptcy after 125 years of operations when its business model stopped generating positive cash flow. ProfitsProfits tell a different story and help shape buying behavior depending on the margin profile. For example, Nvidia, at a 56% net profit margin, has customers “paying whatever Nvidia is demanding” for chips because they see AI-driven value,” he said. Walmart, at 3%, competes on price and efficiency. “A high-margin company is looking at ways you can help them create more value and be more innovative, whereas thin-margin companies are going to look at every penny.”AssetsAssets require a careful balance between two competing priorities: strength, having enough inventory or cash to weather a downturn, and utilization, earning the best possible return on everything you own.GrowthGrowth, Cope says, is less about increasing revenue for its own sake and more about building innovation, competitive position, and upward mobility that attracts talent. PeoplePeople sit at the center of the model because, as Cook put it, “employees anticipating the needs of customers is the key to driving cash, profit, assets, and growth.”From Product Expert to Value ArchitectApplying the five drivers means doing the kind of pre-call homework many sellers skip, using a quick diagnostic to understand where a customer stands, says Cope. For example, if sales are growing but profits are not, the customer likely has a cost problem and will want to focus on efficiencies and budget discipline, while strong profitability paired with stagnant top-line growth signals a need to discuss speed-to-market, innovation, and market access. “If you only knew those two things, you’ve got at least a really good start as you walk in the door,” he added.Different functions within the same customer organization rank the five drivers differently. A chief financial officer fixates on cash flow, margin trends, and return on capital. A marketing leader cares about growth and people. An IT or operations buyer thinks in terms of assets, scale, and cost efficiency. “That language has to be different from meeting to meeting,” Cook said “and the way you articulate solutions also should be very different.”The most practical habit Cope recommends is one many sellers have never considered: listening to the customer’s quarterly earnings call, particularly the prepared remarks from the CEO and CFO. “It will take you about five to ten minutes to do that, but that will tell you what’s really in the mind of not only the CFO but the CEO as well,” he said. Real Results When Business Acumen Meets SalesCook shared proof points from organizations that embedded business-acumen training into their sales teams. A global manufacturing firm found that salespeople who completed the training closed 60% larger deals, averaging 6.5 deals compared with 4.5 for those who didn’t. Cope outlines three non-negotiables for organizations that want to build this capability: training must be customized for the company’s industry, products, and financials; it must be genuinely engaging for sales professionals who may be wary of financial concepts; and it must be actionable. “People have to know immediately how they can apply this content in their sales conversations,” he said.The payoff, Cook suggests, isn’t just increased sales, but a deeper sense of purpose. “You love the products and solutions you’ve got, and you love the customers that you sell to,” he said. “This translative skill set between what you have and the value you can create for them not only drives more meaning to why we should be partners here, but drives more relevance, stickiness, and partnership-mindedness.” That, Cook says, is what separates a vendor from a trusted business advisor, and what turns a stalled deal into a win.Editor’s note: From Day One thanks our partner, Acumen Learning, for sponsoring this webinar. Ade Akin covers artificial intelligence, workplace wellness, HR trends, and digital health solutions.(Photo by Jacob Wackerhausen/iStock)
Aligning HR and Finance for Better Decisions and Stronger Outcomes
BY Emily McCrary-Ruiz-Esparza May 12, 2026Human resources and finance teams tend to diverge when it comes to two things, says Ken Matos, director of market insights at HR software platform HiBob. That’s decision-making and data. When there is a decision to be made about workforce planning, does HR go to finance for permission or a check? And how are those decisions made? HR and finance often have different data, sometimes to describe the same thing, so when they look at the same problem from different angles and don’t agree, they start questioning each other, sometimes suspiciously. Where does this disagreement show up in the organization? “All the way down at the manager level,” Matos said. And it can be disastrous. In a 2026 survey, HiBob asked managers for examples of what happens when missing or conflicting data damages the people decision process, “and we saw some scary things,” he said, like people being put in the wrong pay grade, missing necessary pay raises, or two candidates hired for the same job—and showing up on the same day. During a From Day One webinar on how HR and finance can align for better decisions and stronger outcomes, Matos described in detail where HR and finance often disagree, and how HR leaders can change the story. The misalignment is a time-waster. Almost half (46%) of managers told HiBob they spend three to four hours stitching together data before making decisions, and 62% of managers simply make educated guesses to avoid missing deadlines. The results? Three in four managers say their talent decisions have been challenged in some way in the last year. These are managers making frequent decisions about promotions, pay raises, bonuses, and access to skills training. As Matos put it: “all the things that cost money in your organization.” “That’s where you’re really bleeding money and bleeding engagement,” he said. “When you’re wondering, why is there frustration and burnout for managers? Well, if they spend all this time trying to put together the right info, and they’re struggling to do that, they’re going to end up getting challenged. That sounds like the perfect recipe for burnout.” Journalist and From Day One contributing editor Emily McCrary-Ruiz-Esparza moderated the session with Ken Matos of HiBob (photo by From Day One)But if HR and finance can recognize that they’re trying to solve the same problem, and achieve the same goal, it “allows you to have a much more rich conversation,” Matos said. He gave some advice on how HR can make better appeals to the finance team: Show them money made, money saved, and risk resolved.And in terms of lead time, the more the better. It can take a quarter or two to gather data and make a plan, he said, but if you involve stakeholders early, you’ll earn social capital. “If you’re building it with them, they’ll be like, ‘of course, it took you that long because I needed to get this information, and I didn’t have time to give it to you, but I’m behind it, so let’s make this happen.’” Editor’s note: From Day One thanks our partner, HiBob, for sponsoring this webinar. Emily McCrary-Ruiz-Esparza is an independent journalist and From Day One contributing editor who writes about business and the world of work. Her work has appeared in the Economist, the BBC, The Washington Post, Inc., and Business Insider, among others. She is the recipient of a Virginia Press Association award for business and financial journalism. She is the host of How to Be Anything, the podcast about people with unusual jobs.(Photo by Jacob Wackerhausen/iStock)
The High-Cost Claim Your Benefits Strategy Isn’t Ready For
BY Emily McCrary-Ruiz-Esparza May 07, 2026A new category of pharmaceutical therapy is proving revolutionary for diseases and conditions once thought to be untreatable or inevitably fatal. The downside is their cost, which is bad news for employers and workers already shouldering rising healthcare costs.Some providers are warning that new and novel life-saving treatments could threaten the relative stability of that growth, creating huge volatility for self-insured employers. This was the topic of discussion during a From Day One webinar on the high-cost claim many benefits leaders aren’t ready for: cell and gene therapy. Cell and gene therapy, or CGT, targets disease at the cellular level by introducing new, healthy cells to replace damaged ones. Many cell and gene therapies target conditions once considered hard to treat or even incurable, like sickle cell disease or the brain cancer glioblastoma. Many such therapies are still considered investigational.It’s often cost-prohibitive for patients to pay for these treatments. “They’re new and they’re incredibly expensive,” said Will Shrank, MD, the CEO of Aradigm, a cell and gene therapy carveout provider. “There’s a huge amount of research that goes into designing, developing, and bringing these therapies to market. They’re often used to treat a very, very small number of patients for very rare conditions.” Caitlin Hohman, PharmD, a clinical pharmacist at Quantum Health, spoke during the webinar (company photo)Conversations about CGT are often driven by sticker shock, he says. Cell and gene therapies are a high cost category for self-funded employers, and they can create unpredictable spending spikes, says Caitlin Hohman, a clinical pharmacist at Quantum Health, a healthcare navigation firm partners with Aradigm to provide CGT coverage through employers. Their data shows that a single member can potentially trigger a $4 million claim, which makes it tough, if not impossible, to budget and plan for therapies like these. Plus, she said, “there’s not a pre-existing or industry standard on rates for these drugs.”Claims are often subject to single-case negotiation with no benchmark for what an employer pays. There’s also little infrastructure for post-treatment monitoring, which makes it hard to track the outcomes for patients. Additionally, many CGTs get accelerated approval, and durability is still being studied.“Put all these factors together,” said Hohman, “and you’re creating such a uniquely unpredictable financial landscape for self-insured employers, specifically.”There’s year-over-year volatility too, with per member per month costs fluctuating significantly over time. And it’s not the result of a single outlier, Hohman says. “Over the last five years, we’ve had employers show up consistently across multiple years with cell and gene therapy claims, which tells us this is an ongoing exposure.” Employers of all sizes are feeling the impact. While small companies are disproportionately affected, even large employers are seeing $1 million to $2 million per member per month cost, according to Quantum Health data.Shrank said Aradigm is able to mitigate some of these costs thanks to the volume of patients they manage. They charge employers a monthly premium, where risk is capped, pooling those funds into a larger pool to ensure price stability. Employers pay nothing beyond those premiums.By building a national network of providers, Aradigm guarantees them more volume, and in return, they get discounts from manufacturers, in some cases based on patient outcome, which means some dollars return to the pool when treatments aren’t successful. While Aradigm works behind the scenes, Quantum is a single point of contact for patients, which enables the company to form what Shrank and Hohman describe as a “bear hug” around the patient. “From an operational perspective,” said Hohman, “there is such an identified need in this space to support patients and providers with end-to-end coordination, before, during and after administration of these drugs.”Care navigation is critical, Hohman says. “Employers are coming to us for help navigating applicable benefits and putting the pieces of the puzzle together—because there are so many pieces out there.”Editor’s note: From Day One thanks our partner, Quantum Health, for sponsoring this webinar. Emily McCrary-Ruiz-Esparza is an independent journalist and From Day One contributing editor who writes about business and the world of work. Her work has appeared in the Economist, the BBC, The Washington Post, Inc., and Business Insider, among others. She is the recipient of a Virginia Press Association award for business and financial journalism. She is the host of How to Be Anything, the podcast about people with unusual jobs.(Photo by metamorworks/iStock)
What's Going On? How You'll Finally Solve the Age-Old Marketing Question in 2026
BY Paul Kersey May 07, 2026AI has turned marketing into a high-speed content machine. But as the volume of AI-created content explodes, marketers face a new challenge: standing out while maintaining quality, consistency, and a recognizable brand voice.George Huff, CEO of Opal, suggests that marketing leaders fight fire with fire, harnessing specialized computer systems and AI to track output and guide creative professionals. He spoke during a thought leadership spotlight at From Day One’s Silicon Valley marketing conference, sharing his approach to a software suite tailored for marketers, one that enables collaboration and streamlines the organization of content throughout the production process.Huff had long been fascinated by marketing, especially the creation and growth of brands. As a young consultant in Portland, Oregon, in 2012, he had a front-row seat as Nike expanded its footprint in athletic shoes and apparel. One moment that stuck with him was how difficult it was for Nike executives to monitor the output of their large marketing team. As both sponsor and outfitter, Nike was deeply involved in sporting events around the world, yet leaders often struggled to see what their teams were actually producing for those events.That disconnect stood out at a company that otherwise excelled at building and protecting its brand. Recognizing the challenge ultimately led Huff to start Opal, a company focused on helping organizations better manage and coordinate marketing teams and their work.George Huff, CEO of Opal, led the session“We’re almost like anthropologists of marketing teams and marketing workflows,” he said. What the team at Opal has found is that there are serious structural impediments that make marketing teams difficult to manage. The creative people who generate the content tend to work as individuals, and the system has to allow them freedom, he says.But assembling and organizing the material they generate, including text, images, audio, and video, requires a significant amount of time and labor. Information has to be compiled into memos or slide decks. It does not happen automatically. It then has to move up and down a multilevel corporate structure. Meetings can be lengthy, and there are often moments of panic when things go wrong and executives need to be quickly brought up to speed on content they are not familiar with.All of this results in what Huff calls “friction.” The process is laborious, and each level of bureaucracy creates room for misunderstanding. Executives can’t always get a quick response if they want to know what content is being created for a key event. And if they can’t see the material quickly, they can’t respond quickly to problems and shape the content so it fits the company’s marketing strategy.Things will likely get worse before they get better. This year, roughly half of marketing content will be AI-generated, says Huff. Much of it risks turning into slop: images of people with extra fingers, or copy that feels choppy and mechanical. Even if teams are sharp-eyed enough to catch the obvious AI-generated mistakes, the sheer volume of content will make tracking, reviewing, and evaluating everything far more time-consuming than it is today.Opal’s vision is to make content generation a more “multiplayer mode” process, using software that encourages collaboration while simplifying the collection and distillation of content into formats that are easy to review, says Huff. Its platform helps teams organize campaigns and events, making it easier for managers to identify and evaluate content as creative staff collaborate.By streamlining coordination and oversight, the goal is to help executives ensure that marketing output stays aligned with a company’s brand and overall strategy. “We believe that alignment should be a low friction activity” Huff said, as opposed to fire drills. Huff’s goal is to make much of the alignment work automatic, so executives, managers, and content creators can focus on delivering a great experience for customers.Editor’s note: From Day One thanks our partner, Opal, for sponsoring this thought leadership spotlight. Paul Kersey is a former attorney and freelance writer who has covered events for Bloomberg News and other outlets. Paul is based in Chicago, IL.(Photos by Josh Larson for From Day One)
Solving Before Sourcing: A Smarter Model for Executive Hiring
BY Emily McCrary-Ruiz-Esparza May 05, 2026The best hires often come from unexpected places. This might be most surprising at the executive level.A few years ago, Bert Hensley, the CEO of executive search firm Morgan Samuels Company, was working with a young and newly installed head of a Fortune 500 healthcare company. Because of his age, he wanted to pack the C-suite with highly experienced leaders, and the board insisted they come from within the industry.But the goals they set for the role—mostly to do with operational excellence—weren’t reflected among healthcare leaders at the time. Hensley recommended they look outside the field at people with experience working in highly regulated industries, managing huge, cybersecurity risks, and handling billions of transactions per day. The new hire, who came from telecom, was such a success that a few months later, the CEO told Hensley that “every board member swears it was their idea to look outside the industry.”“There’s an illusion that prior experience is a proxy to future success,” said Sandy Gould, the chief people officer at LGBTQ advocacy organization GLAAD, who joined Hensley for a From Day One webinar about better strategies for executive sourcing. Such a limited view creates tunnel vision that excludes some of the most capable and adept candidates. Bert Hensley, CEO and chairman of Morgan Samuels, pictured, spoke with moderator Emily McCrary-Ruiz-Esparza during the virtual session (company photo)When recruiting for the C-suite, or at any level of an organization, you’re seldom looking for a resume, “you’re looking for their ability to solve a certain set of challenges with certain variables in play that are inherently different at every organization,” Gould said. “It’s about adaptability and capability.”The two met decades ago when Hensley was hired to help recruit for high-level positions at the financial institution where Gould was working at the time. The company wanted to change the way it had been conducting executive search, moving away from traditional, narrowly focused ways of recruiting and toward building deeper, long-term relationships with talented leaders of all backgrounds.Hensley’s strategy was new from the word go. Gould described previous search partners who would show up to the meeting with their minds made up about who should fill the role and what their goals should be. “I’m like, ‘Wait, how do you know? Are you psychic?’” he said with a chuckle. “Having somebody come in with curiosity is important.” Hensley arrived eager to learn about the organization. “It takes a lot of effort up front to really define the problem you want an executive to solve,” said Hensley. While it’s important to identify the frustrations with whoever previously held the role, the focus should be on future results: What does this person have to get done in the next 24 months? In what market(s) will they work? How many deals do they need to make? Of what size?Company culture matters too. That is, an honest, clear-eyed view of company culture. To do the job well, new executives must be privy to the good and bad parts of culture, and that means the current leaders need to face the problems too. Every company has them. Does one department tend to clash with another? Are there deep-running office politics? Identify it, talk about it.One of the most common traps of traditional executive search is that “almost all clients confuse confidence with competence, but there’s zero correlation,” Hensley said. “Zero.” In fact, Gould and Hensley said, humility and willingness to say I don’t know are marks of the best leaders. And you can ask for specifics. In fact, you should. “You need to go deep into granular details and examples after you give principles about how you work,” Gould said. “A lot of people stay at a high level, which is not satisfying or helpful.”It’s not unlike ordinary behavioral interviewing. Gould suggested this exercise: “Talk about a situation where there was a tremendous amount of change going on. How did you adapt and respond to it? What part did you contribute to driving change?” And if you’re looking for a leader who’s not afraid to change the way things are done: “What permission did you have? What did you do when people opposed you? How did you convince them?”“What we have found through thousands and thousands of searches is that candidates who do the best are really into the details, even if they’re the CEO,” said Hensley. They can talk about what they were doing a decade ago. They’re ready to talk about mistakes they made and what they learned. “Nobody ever sets a perfect plan. None of us.”Hensley has found a correlation between executives who can work in the details and those who are inspiring leaders. Those with command and control personalities, who want to preside over teams rather than lead them, tend to resist dealing with the small stuff and are unwilling to learn.Gould’s mindset is that “learning is always right, knowing is always wrong.” Because learning means you remain curious. And if you want to know who’s curious, you have to spend time with them. “Some of our absolute best placements,” Hensley said, “are people whom we took the time to really get to know.”Editor’s note: From Day One thanks our partner, Morgan Samuels Company, for sponsoring this webinar. Emily McCrary-Ruiz-Esparza is an independent journalist and From Day One contributing editor who writes about business and the world of work. Her work has appeared in the Economist, the BBC, The Washington Post, Inc., and Business Insider, among others. She is the recipient of a Virginia Press Association award for business and financial journalism. She is the host of How to Be Anything, the podcast about people with unusual jobs.(Photo by mesh cube/iStock)
Brand Worlds Are the Next Marketing Frontier
BY Grace Turney April 29, 2026Chad Reynolds spent 25 years traveling the world to understand consumers. He interviewed people in their homes, in markets, in unfamiliar cities, only to return and watch those hard-won insights get second-guessed in a conference room. The problem was never the ideas; it was the room itself.“I always dreaded entering this room,” Reynolds recalled, describing the classic focus group setup. “It wasn’t the people, I love people. It was just, they had no real context for what we were trying to solve. It was luck of the draw.”That frustration became the foundation for Vurvey Labs, the AI company Reynolds founded and now leads as CEO. During a thought leadership spotlight at From Day One’s Silicon Valley marketing conference, Reynolds laid out a sweeping vision for what he calls “people models,” or AI systems built not from scraped internet data, but from millions of real human voices, emotions, and behaviors. His argument: companies that keep treating AI as a productivity tool are missing the bigger opportunity entirely.Real, Synthetic, and SurrealReynolds frames the current AI landscape as operating across two modes: the “real” world, where human beings live, feel, and act irrationally, and the “synthetic” world, where AI agents and simulated environments do what they’re programmed to do. Most companies, he says, are stuck at one pole or the other.The more interesting territory, he says, lies between them—a space he calls “surreal.” Borrowing from the artistic movement that sought to surface unconscious, dreamlike states, Reynolds uses the term to describe a mode of thinking and building where human experience and artificial intelligence genuinely synthesize.Chad Reynolds, CEO & Founder of Vurvey Labs, led the thought leadership spotlight in Silicon Valley “Surrealism actually started as a writing movement, not painting,” he said. “When you think about how we experience the world in different ways, to truly take advantage of what AI can do, you have to live in that surreal space, because that’s where all the messy stuff happens. Where a consumer likes something one minute, and completely changes their mind the next.”Most AI systems, Reynolds says, are optimized for language but not for people. Large language models are trained on internet data that skews toward the average, producing what he calls “the mean,” the top of the bell curve. “That’s great,” he said, “but I want the edges. I want the whole bell curve. That’s where the gold lives—in the people who see the world differently.”Building a Haystack of NeedlesVurvey Labs takes a different architectural approach. The company, whose name is short for “video survey,” holds a patent on a video-based survey method that pushes questions to the phones and devices of more than 3 million people around the world. Their responses, including not just text but also video and emotional expression, feed into what Reynolds calls a “people model” rather than a conventional language model.From that foundation, the platform generates synthetic consumer populations, not single AI personas, but thousands of distinct individuals drawn from real behavioral and contextual data. The goal is to move consumer insight beyond the familiar archetype of “Jane,” a persona trapped in a PowerPoint deck, and into something dynamic.“What if Jane could talk back?” Reynolds said. “What if it wasn’t just Jane, but thousands of other Janes with all different types of lived experience, from all over the world, who could give you feedback?”The platform is already in use at scale. Unilever, an early adopter, has rolled it out across more than 30 markets and all major categories—generating AI populations of consumers for brands like Dove and Hellmann’s, says Reynolds. Rather than restricting consumer insights to research teams, the approach lets product, marketing, and innovation staff across the company test and develop ideas directly with simulated consumer segments.“We always talk about being consumer-centered or consumer-obsessed,” Reynolds said. “This has been an amazing way for companies to have their senior leaders say: here is the consumer. We’re distributing them to everybody in the company.”Focusing on Audience Specificity and PreferencesOne of the more striking applications Reynolds shared was what Vurvey Labs calls the “neuroverse,” a population of neurodivergent consumers built from recruited participants across the autism spectrum, with ADHD, dyslexia, and other conditions, including non-verbal individuals and those who contributed via sign language.The motivation, Reynolds says, goes beyond inclusion as a value. More than 53% of Gen Z identify as neurodivergent, he noted. For any brand targeting that generation, ignoring the neurodivergent population means missing roughly half the audience, and potentially designing communications that simply don’t land.During this past year’s Super Bowl, Vurvey Labs ran the entire ad lineup through the neuroverse population in parallel with the general public. The results diverged significantly. The Budweiser commercial ranked first in USA Today’s Ad Meter among the general audience. Among the neurodivergent population, it scored far lower. The gap, Reynolds says, is precisely the kind of signal that traditional focus groups and even most AI tools would never surface.“It wasn’t to critique the ad,” he said. “It’s just to understand, as you’re trying to design stories, how do you actually engage the entire audience? You don’t need to be relevant for everyone, but you should understand how to be more accessible and how to deliver a message that lands.”The same logic drives other niche populations the company has built, including a database of nearly 47,000 contractors for a major home improvement retailer, enabling that company to test concepts, loyalty programs, and product ideas with a hard-to-reach audience at scale and in real time. Simulation as Standard PracticeReynolds predicts that within three to six months, the word “simulation” will become ubiquitous in business conversations—a shift as significant as when “cloud” or “platform” entered the mainstream lexicon. The analogy he reaches for is Sim City: a world you build, control, and test inside before committing to it in the real one.“Rather than the rest of the world having access to it, you and your team have access to it,” he said. “You can test ideas. You can build things. You can explore the future.”He was careful to frame the technology not as a replacement for human research, but as a complement to it. Vurvey Labs runs ongoing validation studies, comparing what its populations surface against findings from interviews with actual humans. What has surprised even Reynolds’ team is that the AI populations sometimes raise themes that humans don’t explicitly name – but immediately confirm when those themes are reflected back to them.“They just didn’t want to talk about them,” he said. “So what can we learn by understanding what’s in the subtext of what our consumers are saying? Can we actually increase what we’re discovering?”The design school metaphor Reynolds keeps returning to captures the spirit of what he’s building: a system where you put your idea on the wall and let a diverse, critical audience tear it apart, not to discourage creation, but to sharpen it. The difference is that the audience now numbers in the thousands, spans the globe, and is available at any hour.“For us to get somewhere new,” Reynolds said, “we need people models to exist. It’s less about a tool, and more like entire worlds we’re building.”Editor’s note: From Day One thanks our partner, Vurvey Labs, for sponsoring this thought leadership spotlight. Grace Turney is a St. Louis-based writer, artist, and former librarian. See more of her work at graceturney17.wixsite.com/mysite.(Photos by Josh Larson for From Day One)
Stop Chasing AI, Fix Your Content Foundations First
BY Kristen Kwiatkowski April 28, 2026Chasing AI at scale can just as easily create problems at scale. That’s why you need to focus on your content foundations first before putting AI to good use. There is pressure as AI raises expectations, but a clear gap remains: most content foundations were not built to scale. The good news is that this creates an opportunity. With the right foundation in place, AI can deliver on its promise. These topics were explored during a thought leadership spotlight at From Day One’s Silicon Valley marketing conference, in a conversation between Misti Vogt, SVP of engagement at Orange Logic, and Kathleen Cameron, senior digital asset operations manager in marketing operations at Google.“Everyone is being pushed to adopt AI faster,” said Vogt. “From your perspective, what do marketing leaders need to understand before they invest further?”Cameron highlighted that the importance of understanding the underlying architecture and making sure those foundations and governance are in place are key components. “You’re going to want to string all of that data together from all of your different tools and that's where you’re going to get a lot of that benefit from those AI tools to get either the analytics or understand how to make those quick changes to those assets to improve performance out in the market,” said Cameron. Without those foundations, you’re making things up as you go without the benefit of the data, Cameron says. As for the difference between an organization that experiments with AI and one that builds the foundation to benefit from it, Cameron says the two can exist in parallel. Experimentation is valuable, but organizations also need to account for regulatory compliance, which requires a more careful approach. You can experiment in a controlled environment and figure out where AI can benefit you. If you don’t have a strategy, look at what your information architecture is.Misti Vogt, SVP of engagement at Orange Logic, spoke with Kathleen Cameron, senior digital assets operations manager, marketing operations at GoogleMeanwhile, there is a strong push to deploy AI widely while personnel budgets are being cut, but information security teams are urging caution, saying it is not ready for broad use yet, Vogt says. That leaves operators stuck in the middle. “So, this is where experimentation and creating those guardrails allows you to continue to move forward while you're making sure that the security team has all the information they need to feel comfortable,” said Vogt.“I think we’re all feeling the friction of the tools evolving so quickly,” said Cameron. “I’ve had the experience of tools changing throughout my career, but not at this speed. And we want to embrace new tech, and I think we just need to do it more responsibly and thoughtfully,” she said. When people come to Vogt with questions about AI, she first asks what problem they are trying to solve. Once that is clear, the path forward becomes more focused and manageable.How Content Is Created and ManagedAs for what assumptions marketing teams should rethink, particularly around how they create and manage content, Cameron says the way content is produced is changing rapidly. It is important to examine every component, including copy, video, and photography.She emphasized the need for caution, especially when it comes to existing agreements and rights holders, in order to protect the brand and its reputation. Teams also need to stay alert to new regulations as they emerge.“Every piece of content that exists for your business should understand when it was created, why it was created, how much it cost to create, which teams engaged with it, how it went to market, and how it was recomposed,” agreed Vogt. “Throughout the entire content journey, there’s a lot of value there, regardless of the audience or channel,” said Vogt. “Localization is a big one. I think everyone in this room has some kind of localization effort underway, and many are working with third-party localization agencies, but the rules are pretty similar. As long as we track those rules and can dynamically compose the elements, it starts to streamline the process and allows creatives to do what they love to do, which is be creative.”Editor’s note: From Day One thanks our partner, Orange Logic, for sponsoring this thought leadership spotlight. Kristen Kwiatkowski is a professional freelance writer covering a wide array of industries, with a focus on food and beverage and business. Her work has been featured in the Bucks County Herald, Eater Philly, Edible Lehigh Valley, Cider Culture, and The Town Dish. (Photos by Josh Larson for From Day One)
How to Support Employees Through Rapidly Changing Times: Top HR Priorities
BY Kristen Kwiatkowski April 27, 2026When priorities shift, structures evolve, or new expectations take hold, employees are often left figuring out what to do first and how to keep up. That’s where HR can make the difference, helping turn uncertainty into something people can actually navigate.Janine Yancey, founder and CEO of Emtrain, an online compliance and culture training with workforce analytics company, provided insight on this topic during a thought leadership spotlight at From Day One’s Silicon Valley conference. She offered insight into four distinct ways that HR professionals can help their team adjust to rapidly changing times. Business transformation, especially when technology begins to automate roles once handled entirely by people, forces employees to adapt quickly. At the same time, HR leaders are navigating a mix of new workforce technologies, reorganizations and reductions in force, gaps in management skills, and growing pressure on culture and engagement.The Top HR PrioritiesNew technology is the first top HR priority, especially with AI. As more companies utilize AI, it’s important to ensure your team is proficient with AI tools and determine what the work ratio looks like and what the outcomes are. Go to other departments and teams to shadow, assist, and observe what’s going on in these other teams.Once you feel confident that your team is proficient with the new technology, the next step is to see how the employee roles might shift, says Yancey. “My recommendation is to be proactive,” she said. Yancey recommends that HR leaders assess what their teams can do differently with new technology in place, then evaluate each role to redesign the organization accordingly and bring that plan proactively to the C-suite. “For decades, HR leaders have been wanting to be the true business partner to the executives,” said Yancey. “And there is no year like this year that gives us all an opportunity to do that.”The next priority is to understand the capabilities of your managers—they’re the glue that basically holds the organization together, says Yancey. “Can the managers lead a diverse, multigenerational team?” asked Yancey. “Do they know how to develop? Do they know how to coach?”Managers who appear to have the strongest leadership skills, based on employee feedback, are often those with the fewest compliance issues. Strengthening these outcomes can be supported through targeted management training.Janine Yancey, founder and CEO of Emtrain, led the sessionManagement training can also help leaders more accurately identify compliance issues and address them effectively with their teams. As organizations invest in management and leadership development, the focus should be on both measuring and building leadership capabilities so managers, leaders, and individual contributors can operate in the most productive and effective way possible, she says.It’s important to try to ask periodic questions in annual management and compliance training. Ask people what’s happening on their teams and map the employee sentiment to behaviors and teams. This will help you know what’s really going on among the teams.Finally, a culture of respect often requires additional attention during periods of business transformation. It’s important to be intentional about integrating programs so they work together in a more holistic way. For example, initiatives like annual culture surveys, leader and manager training, and coaching and development should be viewed as part of a connected system that provides a clearer picture of what’s really happening across the organization, says Yancey. It’s also essential to use data to identify which managers need the most support. With better insights, HR leaders can be more strategic about where they focus their time and effort, ultimately driving stronger outcomes.Editor’s note: From Day One thanks our partner, Emtrain, for sponsoring this thought leadership spotlight.Kristen Kwiatkowski is a professional freelance writer covering a wide array of industries, with a focus on food and beverage and business. Her work has been featured in the Bucks County Herald, Eater Philly, Edible Lehigh Valley, Cider Culture, and The Town Dish. (Photos by Josh Larson for From Day One)
Beyond AI Literacy: Three Ways People Teams Can Lead AI Transformations
BY Carrie Snider April 22, 2026Leaders know they need to adopt AI. But how to actually make that shift can be unclear. At From Day One's Silicon Valley event, Tigran Sloyan, CEO and co-founder of CodeSignal, outlined how organizations can move beyond basic awareness to true AI fluency.His core point: AI isn’t just another tool. It’s a technology transformation, which is something every company has faced before.“Every time we’ve created new technology, we have to teach humans how to use that technology, and that essentially became a job,” he said.History backs this up. The printing press technology reshaped work. The same happened with typewriters and computers. Tasks evolved, and people learned new ways of working. AI is simply the next chapter. “The next phase of AI will do the same thing for the jobs today, where many of the jobs today become tasks of tomorrow.”For people teams, that raises a pressing question: how do you prepare a workforce for something that’s changing this fast?The Role of People TeamsTigran Sloyan, CEO & co-founder of CodeSignal, led the sessionHR and people leaders are at the center of this shift, whether they feel ready or not. According to Sloyan, their role comes down to two priorities: First, define how AI applies to their specific organization. Second, use AI to improve workflows, making work better, faster, and more efficient The challenge is speed. AI adoption is happening quickly and unevenly across organizations.“Doing both of these things is incredibly difficult,” Sloyan said, “because the timeline is highly compressed.” Structure matters. His framework breaks the process into three steps: assess, develop, and deploy. Here’s the three steps to lead AI transformations. Step One: Assess SkillsBefore you can train people, you need to understand where they stand.Sloyan compared AI assessment to learning how to drive. A written test might confirm basic knowledge, but it doesn’t prove someone can actually operate a car. “Imagine how much worse the streets would be,” he said. To get a license, a person must actually get behind the wheel and show the instructor their skills.The same applies to AI. Multiple-choice quizzes can measure familiarity, but they don’t capture real capability. Instead, organizations need practical, hands-on evaluation.“At its core, assessing skills starts from: Can you simulate it?”For example, instead of asking recruiters what they know about AI, place them in realistic scenarios: Gathering job requirements, sourcing candidates, closing hires. Then observe how they actually use AI in those moments.The same approach works across functions. Sales teams can practice negotiations. Customer service teams can handle simulated interactions. The goal is simple: see in-the-moment performance, not just knowledge. Because across any workforce, AI ability varies widely, even in companies pushing adoption aggressively. Without proper assessment, you’re guessing.Step Two: Develop AI Literacy at ScaleOnce you know where people are, the next step is helping them improve at scale. Many organizations struggle because employees aren’t starting from the same place, and they don’t learn at the same pace.“Instead of assuming that everybody is going to be learning at the same pace, you have to continuously measure,” Sloyan said.Hands-on learning becomes critical. Simulations allow employees to practice real tasks while building confidence and skill. More importantly, they create measurable progress.AI literacy isn’t one-size-fits-all. What it means for a recruiter differs from what it means for an engineer or a salesperson. It depends on the role, the company, and the context. That’s why ongoing measurement matters. It ensures no one falls behind—and highlights where additional support is needed.Step Three: Deploy AI Across the Talent LifecycleThe final step is continual learning. AI skills are always changing. As technology evolves, so must the workforce. That means embedding learning into the entire employee lifecycle, not treating it as a one-time initiative. Assessment feeds development. Development feeds application. And the cycle repeats.At CodeSignal, this process is supported by an AI assistant named Cosmo the corgi, which guides employees through assessments and hands-on learning. While the tool itself may vary by organization, the principle is what matters: make learning continuous, interactive, and adaptable. Because even once employees reach proficiency, the target keeps moving.Ultimately, says Sloyan, AI reshapes how people work. Organizations that succeed won’t be the ones that simply adopt AI tools, but the ones that invest in helping their people adapt alongside them. That starts with understanding skills, building them intentionally, and reinforcing them over time. Technology transformations have always required humans to evolve. AI is no different. The difference now is speed and the opportunity for people teams to lead the way.Editor’s note: From Day One thanks our partner, CodeSignal, for sponsoring this thought leadership spotlight. Carrie Snider is a Phoenix-based journalist and marketing copywriter.(Photos by Josh Larson for From Day One)
Are Your Employee Rewards Costing More Than You Think?
BY Christopher O'Keeffe April 21, 2026Employee-recognition programs are intended to boost morale, strengthen retention, and reinforce culture. But many organizations may be unknowingly reducing the impact of those efforts through the way rewards are delivered.At From Day One’s Boston benefits conference, Tray Ross, VP of growth at Corporate Traditions, said common incentives such as gift cards, bonuses, and other cash equivalents often create avoidable tax consequences, payroll complexity, and employee frustration. His message to HR leaders: appreciation programs should feel rewarding to employees while remaining efficient and compliant for the business.Ross says he frequently hears from HR leaders who begin the year energized to launch or refresh employee-recognition initiatives. “They get super pumped that this is going to be the year they roll out an employee recognition program or revamp it,” he said. But once rewards begin reaching employees, confusion can follow when the value is reduced through taxation or the program becomes harder to understand than expected. “Employees don’t understand,” he said. That disconnect can turn a positive gesture into a frustrating experience while creating extra work for managers and payroll teams.The Hidden Cost of Cash Rewards and an Overlooked Opportunity Many organizations underestimate the real cost of taxable rewards, says Ross. Employers may choose to gross up the value so employees receive the intended amount, or allow taxes to reduce what employees ultimately receive. He added that when taxes are passed through to employees, “they don't see the entire value or benefit.”Ross pointed to de minimis fringe benefits as a lesser-known tax-code opportunity that may allow certain modest, infrequent tangible gifts to be excluded from payroll tax obligations. “These particular types of gifts can be excluded from payroll tax,” he said.He referenced occasions such as holidays, birthdays, work anniversaries, and service awards as examples of moments where organizations may have more flexibility in how they recognize employees.The Importance of ChoiceRoss acknowledged that many organizations default to familiar branded merchandise because it is easy to approve and easy to repeat. “You guys have enough t-shirts that have your company logo on it, or sweaters, umbrellas, and mugs.”But he says that appreciation becomes more meaningful when employees can choose items they actually want. “They don’t want another umbrella. They want to be able to get what they want off of their Amazon wish list.”Programs built around catalogs or e-commerce-style selection tools, he says, can still remain compliant while improving the employee experience.Recognition systems should also reflect the realities of today’s workforce, whether employees are remote, hybrid, or in-office. Ross said ease of use matters for both employees and administrators. “You want to keep it easy and simple.” The right program, he says, should scale from a single team to an enterprise-wide initiative without creating unnecessary training or operational burden.Ross summarized what effective recognition partners should deliver: practical compliance support without losing the emotional value of appreciation.“The best recognition partners keep the compliance under control, but the gratitude visible, by allowing employees to get what they want.” For employers balancing budget pressure, employee expectations, and tax complexity, that combination may be the real key to successful recognition.Appreciation should not create hidden costs or unnecessary headaches, says Ross. “We want you to win, and tax free gifting is the best way to make it happen.”Editor’s note: From Day One thanks our partner, Corporate Traditions, for sponsoring this thought leadership spotlight. Chris O’Keeffe is a freelance writer with experience across industries. As the founder and creative director of OK Creative: The Language Agency, he has led strategy and storytelling for organizations like MIT, Amazon, and Cirque du Soleil, bringing their stories to life through established and emerging media.(Photo by Josh Larson for From Day One)
It’s Time for Disruption: Why Caregiving and Backup Care Programs Are Breaking Down
BY Kristen Kwiatkowski April 16, 2026Family care needs aren’t just occasional. Many employees are ongoing caregivers for children, parents, or other relatives. When support falls short, stress rises and PTO gets stretched. So why does backup care break down, and how can employers fix it?This was the topic of discussion at a From Day One webinar titled, “It’s Time for Disruption: Why Caregiving and Backup Care Programs Are Breaking Down,” led by Jess Brown, vice president of marketing for Cariloop.Employers are turning to solutions such as Cariloop, an employer-sponsored caregiving benefit that helps to provide solutions for working parents and caregivers, and other avenues that help caregiving employees with their multifaceted needs. Caregiving Support IssuesDee Brown, TV personality, freelance reporter, and session moderator, stated that the system isn’t working the way that we had hoped it would. “73% of the workforce is caring for someone and nearly half say finding last minute care is very difficult. Additionally, 48% of employers offer caregiving support but only 36% offer backup child care,” said Dee Brown. As a caregiver, she can relate to the need for caregiving options all too well. The state of caregiving is a multifaceted problem and system under intense pressure due to an increased demand and lessened supply, says Jess Brown. She stated there are two types of caregiving supply including family caregivers and professional caregivers. Family caregivers are individuals caring for their family members and this has a direct impact on employment as these individuals are often pursuing a full-time job while handling caregiving duties. Professional caregivers for adult care have been facing shortages and 48 states have reported shortages, according to AARP. “More professionals are leaving the field than are entering the field,” said Jess Brown. Jess Brown is the VP of marketing at Cariloop, a comprehensive caregiving solution for employees (company photo)“The good news is that data is showing us that new licensed child care centers are slowly coming back and rebuilding a little bit year over year,” said Jess Brown. However, waitlists are an issue for parents seeking child care centers and there is an average of 6 months to 2 years on a waitlist. In addition, the cost issue is problematic as well since higher demand than supply equals higher cost, she says.Beyond caring for children, many people aren’t prepared to care for aging parents, making it a daunting responsibility that employers should take seriously.There have been changes in workforce participation in the past few years, says Jess Brown. Women’s workforce participation rates have reduced whereas men’s have started to slightly increase. This may be due to women opting out of the workforce or not being able to work due to caregiving duties.Employers should pay close attention to employees’ caregiving responsibilities, as added stress can impact productivity and drive costs tied to absenteeism and turnover. Care demands can lead to leaves of absence, burnout, mental health challenges, and exhaustion.There are also early signs of backup care breaking down. Employees dealing with issues at home may be distracted at work and more prone to burnout. More visible signals include missed work, increased claims related to family needs, and employees leaving the workforce altogether, says Jess Brown.Why Caregiving Support Benefits Matter There are three core areas of caregiving benefits. The first is backup care, an employer-subsidized benefit that provides temporary solutions when regular care falls through, helping reduce unplanned time away from work. The second is caregiver support, which addresses broader challenges across all life stages, from navigating a parent’s new health diagnosis to finding child care. Lastly, caregiving benefits can include access to discounts and resources, such as marketplaces and child care centers.Traditional backup care models often fall short because, while they help employees search for care, supply is limited, says Jess Brown. The provider networks employers select may also not meet the specific needs of employees and their families. In addition, she said, “we need to invest in programs where 100% of the dollars allocated to sponsoring caregiving costs go directly to the care provider.”Return on investment is an important consideration with caregiving benefits. It includes soft ROI, such as reducing stress that can lead to health issues for employees, and hard ROI, such as measurable improvements in clinical outcomes. Dollar-for-dollar savings should also be part of the equation, says Jess Brown.As for how employers should get started considering the impact of caregiving benefits, they can compare leave claims between those who used caregiving benefits and those who didn’t. Survey data can also be consulted to come up with information regarding caregiving benefits and unplanned leave. The best way for employers to evaluate new or updated caregiving programs is to take advantage of their benefit consultants and ask the right questions regarding planned investments and desired returns.Providing the Benefits That Matter MostWhen asked how these benefits can be used when they matter most, Jess Brown emphasized the need for strong promotion. Employees can’t use programs they don’t know about, and access must be quick and seamless.For organizations new to caregiving benefits, impact can be measured through cost savings if a program is already in place, or by tracking reductions in missed work if one is not. Surveys and year-over-year analysis can also provide insight, she says. Companies that get these programs right tend to see stronger retention. Success often comes from refining offerings to fit both employee needs and budget, sometimes even resulting in cost savings.Jess Brown also noted a disconnect that can exist between the care networks offered and what’s actually available or comfortable for employees to use. In some cases, people don’t even identify themselves as caregivers, which limits uptake.Finally, she stressed that caregiving challenges aren’t solved overnight. Employers need to invest in support and be patient in seeing results. Employee sentiment can be tracked through engagement surveys and qualitative feedback, alongside honest, transparent communication.Editor’s note: From Day One thanks our partner, Cariloop, for sponsoring this webinar. Kristen Kwiatkowski is a professional freelance writer covering a wide array of industries, with a focus on food and beverage and business. Her work has been featured in the Bucks County Herald, Eater Philly, Edible Lehigh Valley, Cider Culture, and The Town Dish.(Photo by jacoblund/iStock)
Building Meaningful Support From Maternity Leave Through Return to Work
BY Grace Turney April 14, 2026As soon as Lauren Smith returned from maternity leave after her first child, she encountered a question that still makes her shake her head: “Is your baby sleeping through the night?” She had just come back after four months away. Her baby was barely old enough to begin sleep training. “That’s impossible,” she remembered thinking, “unless you have one of that very small percentage of babies that do.”It sounds like a small moment, a well-meaning but clueless question from a colleague. But for Smith, senior director at Maven Clinic, it represented something fundamental about how companies misread the return-to-work experience for new parents. They think the hard part is the leave itself.They’re wrong.That insight anchored a From Day One webinar titled, “From Maternity to Return to Work.” Shern-Min Chow, journalist and founder of Smart Media Content, moderated the conversation with Smith, who drew on more than seven years at Maven, during which she also had two children, to share what meaningful postpartum and return-to-work support actually requires.Fragmented Care Is a Core ProblemFor HR leaders, the challenge of building family benefits often resembles what Smith called “a game of Whack-a-Mole,” pulling one lever to address breastfeeding support, another for mental health, another for parenting resources, none of them connected. The experience for employees on the receiving end is just as disjointed, she says.Lauren Smith is a senior director at Maven Clinic, the world’s largest virtual clinic for women and families (company photo)“When your baby is born, frankly, that’s when the healthcare system forgets about you,” Smith said. New parents are left to navigate on their own between OB-GYNs, pediatricians, mental health providers, HR teams, and managers. And that’s before even accounting for complications like preeclampsia or a NICU stay.The consequences are predictable: avoidable emergency room visits, extended leaves, and what Smith called “quiet attrition,” employees who reduce hours or leave entirely because they never felt like they had a plan.Her prescription is a single integrated platform where employees can access postpartum care, mental health support, lactation consulting, pediatric guidance, and return-to-work resources in one place. “You have to ensure that those benefits span clinical, emotional, and practical needs and are not a one-size-fits-all solution,” she said. “Having a benefit like Maven checks a lot of boxes, but it doesn’t just check a box.”Mental Health Doesn’t Announce ItselfOne in seven women report severe depressive moods postpartum—a figure most HR professionals know. What’s less understood is that symptoms can last up to a year and frequently appear in people who have never experienced anxiety or depression before. Among Maven’s own members, nearly a quarter report experiencing anxiety when they join the platform, and the numbers include fathers and non-birthing partners.Smith recounted filling out a pediatrician’s intake form after her son was born, and encountering a mental health questionnaire. “I kept thinking, there is no way I am going to tell this pediatrician that I’ve known for an hour about any of my mental health needs,” she said. She checked boxes to move the process along.That same instinct, to hide vulnerability rather than ask for help, plays out in workplaces every day. The antidote, she says, isn’t just offering mental health resources. It’s proactive outreach: a manager, an HR contact, or an onboarding buddy who reaches out and says, simply, ‘How are you doing?’ “Without that, it feels like, as the individual, you are the one knocking on the door,” Smith said.Return to Work Is a Phase, Not a DateManagers often believe that once they’ve secured paid leave and childcare assistance, they’ve done their job. Smith pushes back hard on that framing. “Women are juggling physical symptoms during pregnancy and then postpartum physical recovery, emotional health challenges, breastfeeding logistics, and just overall identity and career questions,” she said. “Can I be on a promotion track, and how do I do all of this?”When those challenges go unaddressed, women come back without a plan—and they are far more likely to reduce hours or leave entirely.What does a real return-to-work plan look like? Smith said it starts before the employee leaves. A strong pre-leave transition should align on dates, clarify flexible-return policies, build a genuine coverage plan, and (crucially) discuss career path and performance expectations before the leave begins. “It really sets the stage on, we value you as an employee,” she said.That support shouldn’t end when the employee walks back in the door. Maven originally offered three months of postpartum support, which Smith called groundbreaking at the time. “Very quickly after we realized there was a huge gap in needing to extend that even further.” The platform now supports families through the first year postpartum and beyond.The Business Case Is ClinicalFor HR professionals who need to make the case to a CFO or board, Smith offered a direct framing: addressing maternity spend is not a perk—it’s a risk management and equity strategy.Maternity-related costs rank in the top five expenditures for most employers she has worked with. A vaginal birth versus a C-section represents a cost difference of $10,000 to $12,000. A NICU admission can run $30,000 to $70,000 per case. Across more than 25,000 births studied over a decade, Maven has found a 15-20% lower C-section rate and a 28% lower NICU admission rate among its members.In one case study, a Fortune 10 company enrolled nearly 2,000 families in Maven’s maternity and return-to-work program, says Smith. The result: 95% of members returned to work, more than half specifically crediting Maven, and the company saved over $1.2 million annually from increased productivity and reduced attrition.Identity-Matched Care Builds TrustMaternal mortality rates in the U.S. have doubled over the last decade, and Black women face disproportionately higher risk of complications and death during childbirth. Many arrive in the healthcare system already carrying distrust, Smith noted, and with good reason.Maven addresses this through what it calls care matching: using clinical data and personal preferences to pair members with specialists who share their background, identity, and language. A Black female member, for example, would be matched with a Black female care advocate, OB-GYN, doula, mental health provider, and career coach. “What that really does is build trust in a system that has a lot of distrust in it,” Smith said.Across Maven’s provider network, 40% of providers identify as BIPOC and 11% as LGBTQ+, and care is delivered in 35 languages. About 6% of mental health providers in the U.S. identify as Black; at Maven, they account for more than a quarter of mental health specialists.The platform also uses virtual doulas, a concept that sometimes raises eyebrows. But with 36% of U.S. counties lacking an OB-GYN, and maternity wards closing in underserved areas, in-person care is often simply unavailable. Two appointments with a virtual doula have been associated with a 40% decrease in C-section rates at Maven.Leave Equity Matters TooDuring Q&A, Smith was asked about disparities between leave offered to birthing and non-birthing parents. She didn’t hedge. “I am a big fan of equity when it comes to leave,” she said. Shorter leaves for non-birthing parents signal that their caregiving role is secondary, creating long-term effects on family involvement and gender equity at work.Research from Maven finds that 90% of non-birthing parents report parenthood-related anxiety. Same-sex couples, adoptive parents, and parents through surrogacy face the same caregiving challenges as birthing parents and deserve policies that reflect that reality.The thread running through Smith’s advice is consistent: stop treating maternity and postpartum support as a checklist and start treating it as the high-variance, deeply personal medical and emotional experience it actually is. The employers who do that, she says, end up with not just healthier employees, but also stronger teams, better retention, and a measurable return on investment.Editor’s note: From Day One thanks our partner, Maven Clinic, for sponsoring this webinar. Grace Turney is a St. Louis-based writer, artist, and former librarian. See more of her work at graceturney17.wixsite.com/mysite.(Photo by JLco - Julia Amaral/iStock)