Built to Last: What the First Ten Years Taught Us About What’s Next

A conversation with Sanish Mondkar, CEO and Founder of Legion Technologies

Ten years ago, Sanish Mondkar didn’t set out to build a workforce management company. He set out to solve a problem: why do hourly workers leave, and what would it actually take to change that? That pursuit led to a clear answer: traditional workforce management was part of the problem. So, Legion rebuilt the category from the ground up.
As Legion marks its tenth anniversary, we sat down with Sanish to reflect on what the company got wrong, what it got right, and why the most consequential decade is still ahead.

What We Actually Set Out to Do

“When we started Legion, we didn’t actually think about workforce management as a category. We wanted to focus on how to make labor more efficient and employee experience far more elevated. Workforce management happened to be the category that came in the way, serving a different set of goals. So, we had to disrupt it to achieve what we actually wanted to achieve.”

That framing, customer outcome first, category second, has shaped how Legion has operated ever since. And it’s driven the way we’ve redefined what workforce management should deliver.

What We Got Wrong Early On

Sanish is direct about early missteps. In year one, Legion had rich data on what was driving employee turnover, but operators kept pushing back with something the data couldn’t capture: firsthand knowledge. They knew specific employees who had left, the real reasons why, and the on-the-ground context that no survey ever surfaces. “You have to talk to customers,” Sanish says. “You have to get the real-world examples.”

The lesson stuck: data tells part of the story, but the facts that matter most come from customers. Today, that belief is built into how Legion operates. Product innovations are co-created with customer conversations, not in siloed dashboards, and real-world context carries as much weight as the data itself.

The Hardest Moment: Navigating COVID

In early 2020, Legion was weeks away from launching its Series B funding round. Investor packages had just gone out when the world shut down. The company’s core customers in physical retail and hospitality were closing en masse.

“We sent packages to more than 50 investors and heard nothing back. In our minds, yes, this COVID thing was happening, but we didn’t understand how quickly it would escalate into a true black swan event.”

The team pivoted fast, adding in-app communication tools, supporting customers through store closures, and working through the uncertainty together. The twelve months that followed produced record-breaking revenue growth. Legion closed not just Series B, but Series C the following year.

“Great teams find a way,” Sanish says simply. “That period proved we had one.”

What a Decade Teaches You

Asked what separates durable companies from temporary winners, Sanish comes back to the problem, not the product. “Is the problem you’re solving material? Is it pervasive? Is it likely to persist? That’s the definition of a durable problem, and it’s a good high-level indicator of whether you’re building a durable company.”

He distills a decade of operating into three principles:

• Stay focused on what customers want. Not just what they say today, but where their business is going and what they will need tomorrow.
• Organize your people and execute with urgency. Growth companies have limited time and a limited runway. Progress is not optional.
• Keep the mission as your true north. “Not all days are great days. What keeps me grounded is remembering why we are here: to turn hourly jobs into good jobs. That is the antidote against the bad days.”

The Next Ten Years: AI, Agents, and Accountability

Sanish is bullish on AI, but clear-eyed about where the hype ends and the hard work begins.

“AI has evolved from surfacing insights to generating actions. Now we’re at the threshold of something bigger: end-to-end automation of entire business processes. Not just a task, but an entire workflow. An agent that can reason, act, and get things done.”

For workforce management specifically, the opportunity is enormous. Even if a WFM platform is executing perfectly within its stated scope, roughly 90% of labor management costs reside in the surrounding operational work: verifying pay files, feeding forecast models, nudging employees to enter preferences, processing time-off requests, etc. Agents, Sanish believes, are built for exactly this: the fragmented, manual work that sits between systems and slows everything down.

But he’s equally focused on what AI has to earn: trust. The gap between an impressive-looking answer and a reliable one is real, and customers will increasingly demand accountability for both.

Legion is building directly toward that. This month, the company is introducing a “prove it” capability in its AI assistants: a multi-level verification engine that checks every number in an AI-generated answer against underlying data, validates the narrative conclusions, and confirms the scope of the analysis. “Citations ask the user to do the work,” Sanish says. “We want our AI to show its report card.”

Leadership in the Age of AI: Everyone Becomes a Builder

Over the last decade, Sanish says he’s learned to prize a specific kind of person on the team: someone who can build but who also has a strong sense of why. What outcome is a product, feature, or campaign actually meant to drive for the customer and the business? “It goes hand in hand with customer empathy. When you get the right person who already thinks that way, it comes naturally.”

But the bigger shift in leadership over the next decade, he argues, isn’t about finding those people. It is about the fact that AI makes that potential available to everyone.

“With AI, everybody has the potential to be a builder. You’re bound only by your imagination, which is the only real constraint at this point. If you’re in finance and you’re doing the same analysis every week, build an agent to do it and free yourself for higher-value work. If you’re in content, the applications are obvious. If you’re a leader running operational reviews, where all those spreadsheets and decks are essentially a summarization. You don’t have to wait for tools. You can build an agent right now.”

The leadership imperative, in his view, is simply this: embrace that change before it happens to you. The bar for what any individual can build is falling fast. The only question is whether leaders create space for their teams to use it.

What We Hope People Say at Year Twenty

After a decade-long conversation spanning a pandemic-era fundraise, AI hype cycles, and the structural forces reshaping labor operations, Sanish lands on something quieter than any of it.

“Ultimately, AI is the how. What I hope people say ten years from now is that our focus on employees in the workforce management equation really elevated their experience and reduced turnover for entire industries. That’s the founding thesis of Legion. That’s the impact I expect us to have.”

Ten years in, Legion is still driven by the same mission: turning hourly jobs into good jobs. The tools will keep evolving. Our aim remains the same.