The HR technology landscape didn’t arrive at its current complexity overnight. While many of today’s leaders may not have lived through three decades of platform evolution firsthand, the industry has—from the dot-com era’s monolithic systems to Web 2.0’s “all-in-one” platforms, through the SaaS boom that fueled a massive unbundling of tools, and now into an AI-powered cycle of rebundling and automation.

During a thought leadership spotlight at From Day One’s November virtual conference, Alex Uhre, enterprise sales manager at Rippling, walked through this history to share how HR leaders can make smarter, purpose-driven technology decisions. “Companies above 1,000 employees on average have 177 SaaS technologies within their organization,” he said. 

Employees feel that burden acutely: “It creates this position that not only are employees a little bit frustrated about trying to figure out where to go, but we’re also finding that even when you do have these all in one systems for our administrators, they’re finding themselves hamstrung.”

Against that backdrop, Uhre outlined a clear, three-pillar framework: buy for the employee experience, choose unification over integration, and adopt new systems with a methodical mindset.

How We Got Here: The Four Cycles of HR Technology 

Uhre opened with a rapid but revealing history lesson.

In the dot-com boom, he said, “desktop technology and desktop information and personnel records transitioned into this idea of the HR information systems that we know today.” These early monoliths centralized employee data and automated payroll, replacing paper systems with digital infrastructure.

The rise of Web 2.0 expanded this further. “We saw this rise of ‘integrated technologies’ where it wasn’t just about the employee records. We wanted to see technology expand to more of the practical day to day things that HR was taking care of.” Recruitment, onboarding, and performance tools all moved under the umbrella of the “all in one.”

Then came SaaS—and a structural shift. “We saw this unbundling of technology,” Uhre said, where organizations adopted “individual point solutions that provided exactly what they needed.” The gain in specialization created an explosion in total platform count.

Now the pendulum is swinging again. “AI is here, massive automation is here,” Uhre said. “We can unify systems again. We can rebundle systems to give HR and business professionals holistic systems that provide exactly what they need.”

The Three Pillar Framework

Too often, Uhre said, HR tech is marketed around “what saves HR time.” But he encouraged leaders to rethink the goal altogether: “I’d love to shift this mindset from saving HR time to reducing friction for your employees.”

An employee tech journey audit offers a practical starting point. “Talk to all of your individuals within your organization,” he said. “From the first day that they join your company, throughout the life cycle of their employment, where is it that they’re finding inefficiencies, and where can things be better?” And utilization is what determines value. “Utilization is the true test,” he said. 

The proliferation of disconnected systems has created what Uhre called the modern “Frankenstack.” “APIs are great. Integrations are fantastic,” he said, “but they’re a bandage for what could be structural redesign.”

The cost of this patchwork approach is significant: dual maintenance, data discrepancies, compliance risk, manual work, and fragmented reporting. “Efficiency comes from data talking to itself,” he said, “not having administrators check on APIs or check on integration.”

Uhre shared the diagnostic question he urges leaders to ask vendors. First, “If you make a change to an employee, how many systems does that need to touch?” And, “Am I able to report on everything entirely in one single report?”

Even at Rippling, the impact of unification is visible. “It should start and stop with as few systems as possible.”

The third pillar, he says, rather than roll out new platforms in one sweeping change, Uhre advises leaders to identify a minimum viable rollout. “When you have a unified system, you are actually able to roll out individual pieces over time,” he said. 

He urged teams to start with high-impact, low-friction improvements: “Maybe it’s expense reporting, maybe it’s PTO requests, things like that.” He also emphasized the importance of measuring everything. “I would really ensure that you are measuring adoption and gathering feedback,” he said. “If it works, promote it. If it doesn’t, let’s fix it before we launch the next module.”

Across every stage of the framework, Uhre returned to one theme: clarity.

The Way Forward: Purpose-Driven Decisions in an Era of AI and Complexity

As the industry enters another major inflection point—this time shaped by AI and automation—the lesson from Uhre’s session is clear: companies cannot afford accidental tech stacks.Unification, intentional design, and employee-first thinking are no longer differentiators; they are survival strategies.

And while the tools have changed dramatically since the dot-com era, the goal has stayed the same: making work easier, clearer, and more connected for the people at the center of it.

Editor’s note: From Day One thanks our partner, Rippling, 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 Thawatchai Chawong/iStock)