Chitra Kanagaraj spent most of her career solving enterprise problems before an ordinary Tuesday afternoon changed everything. Her spouse (and co-founder) drove to school pickup only to come face-to-face with the wrong child in the car. Everyone was safe. The mistake was caught quickly. But that split second — what Chitra calls their "oh sh*t moment" — was unshakeable.
She looked for a solution, found nothing, and decided that if no one had built it yet, maybe that was the point. Today she's COO and co-founder of PikMyKid, a school safety platform serving the 140,000 schools in the U.S. that are still reuniting hundreds of kids with their families every afternoon via walkie-talkies and controlled chaos.
When I sat down with Chitra on Work Made Human, we talked about what it actually takes to build something that solves a real problem — and what it looks like to do it without losing yourself in the process. Here are three things I learned.
Frustration Gets You Started While Expertise Gets You Through
Chitra is clear about what gave her the first push: pure parental shock. But what gave her the confidence to actually build something? Years of enterprise problem-solving that she didn't even know she'd been storing up.
She went to the market first, the way any of us would, but found nothing. And instead of seeing a dead end, she saw a serious gap — one that existed in 140,000 schools, not just hers. That reframe, from "I have a problem" to "we all have a problem," is what turned a frustrated parent into a founder.
What I loved about this is that Chitra didn't position her corporate background as something to escape. She positioned it as the permission slip. The frustration got her out the door. The expertise kept her moving (and building) once she opened it.
Stop Waiting for the Perfect Plan And Fail (with Intent)
Chitra launched PikMyKid through the USF Connect incubator — part of the very first cohort, at a time when Tampa Bay's startup ecosystem was still figuring itself out. She describes those early days as learning to operate without the guardrails corporate life had quietly given her. There was no structure waiting for her and no team of resources. Just: you have an idea, now go.
The mindset shift she had to make? Stop waiting for clarity before moving. Corporate trains you to plan for every risk before you step. Founding a company teaches you that the step is the plan.
But she was careful to distinguish this from reckless experimentation. Her version of failing forward comes with a caveat: fail with intent. Go in wanting to make it work. Have a thought for what comes next if it doesn't. "If your goal isn't failure," she said, "it's a better way to learn."
Relationships Are the Foundation for Everything
Chitra and her co-founder are also husband and wife! So yes, sometimes dinner conversations become product roadmaps and road trips become strategy sessions. She's honest about how hard it was at first to find the line — and how intentional they had to be about drawing it.
What they figured out eventually was to know each other's rhythms and protect them. Chitra is a night person. Pat Bhava, Co-founder and CEO, does his best thinking in the morning. As simple as it sounds, naming that and respecting it changed everything. You stop accidentally blowing up each other's focus time. You come to work with clarity instead of friction.
That same logic now shapes how they onboard every new team member. The first week isn't about the product, it's about the person. What are your non-starters? When do you need to be left alone? When's your kid pickup? Because when people feel seen, Chitra says, they don't trade work for life or life for work — they show up fully for both.
Most of us aren't building companies with our partners. But the principle translates everywhere: Relationships built on real trust and real empathy are what let people go above and beyond. Not perks, snacks, or ping pong tables. Trust.
Listen to the full episode of Work Made Human to hear more from Chitra Kanagaraj — including why she swore as a kid she'd never be an entrepreneur like her dad (spoiler: it's in the genes), what it was like to be in Tampa Bay's very first incubator cohort, and why she thinks AI is our internet moment — exciting, a little scary, and absolutely not going away.
LEAVE A COMMENT