Andy Hamilton is CEO and cofounder of When Insurance, an AI-powered workforce transitions platform that helps employers and transitioning employees navigate post-employment health insurance options, reducing overall healthcare costs. A serial entrepreneur and tech veteran, Andy brings deep expertise in scaling B2B marketplaces and a mission-driven focus on transforming the employee offboarding experience. His unique combination of operational excellence from building enterprise SaaS platforms and firsthand understanding of HR pain points positions him to revolutionize how companies manage employee transitions.

Previously, Andy co-founded and led ApartmentJet, guiding the company through its successful acquisition by Expedia Group, where he later oversaw operations for the company’s multifamily division. Before that, he served as Chief Technology Officer at CriticalKey, where he helped scale technology solutions for enterprise clients.

In our latest Top of the Ladder feature, we sat down with Andy to discuss his journey into healthcare benefits’ innovation, When’s mission to bring clarity, compliance and healthcare cost savings to employee transitions, and his perspective on the future of tech-enabled support that puts the consumer first.

Could you share a little bit about your childhood background?

I grew up in Glenview, IL, the youngest of three by seven years. It was the 80s, and I had a lot of freedom as a kid. Both of my parents were technical consultants, and my dad was entrepreneurial, he often said he just didn’t like working for other people. I remember when he left his job to start his own firm, and not long after, my mom joined him.

Some of my clearest memories are family dinners where they talked nonstop about work, everything from programming challenges to signing new clients. At the time, I found it annoying and swore I’d never go into computers. But I also watched them take a big risk leaving stable jobs to build something of their own. I recall those early days of their business where money was tight for our family, but I watched them put in crazy hours to grow it into a successful business, eventually selling it, and retiring at 55. Their experience left a lasting impression on me and certainly shaped my career path.

You’ve built and exited multiple companies prior to When, including ApartmentJet, which was acquired by Expedia. Looking back, what were some of the defining lessons from those earlier ventures that shaped how you approach building When today?

Prior to becoming an entrepreneur, I was a technical consultant for several years. I became good at discovery work for new client engagements. I honed my skills for isolating problems and developing custom solutions for my clients. It was that experience which gave me confidence as an entrepreneur to build a business around solving a complex problem with a mix of technology and redefining antiquated processes. The most important lesson I’ve learned from my previous companies is the build process is never linear. As an entrepreneur you need to be flexible and nimble in your solution design. It’s ok if you don’t get it right on the first try. Listen to the feedback, adjust, correct course, but stay true to the problem you sought out to solve and you’ll eventually get there.

What inspired you to start When?

My co-founder and next-door neighbor, Dan Wertheimer, was the original inspiration. He saw the problem long before I did. After losing his job in 2008, pre-ACA, he got a COBRA letter and couldn’t understand why his health insurance jumped from $50 to $800 a month. At the time, he was getting his MBA at Chicago Booth and built the original concept for When, even entering it into a business case competition. Like a lot of good ideas, he got busy with a new job and shelved it.

A few years later, Dan moved in next door and was relentless with pushing the idea on me. He was convinced COBRA was outdated and employers needed a better way to support employees after they leave. Amusingly, I had no idea what he was talking about. It didn’t fully click for me until I was laid off from Expedia during Covid. Going through it myself, the lack of technology, the confusion, and the frustration of that COBRA packet made it obvious. Dan had identified a real blind spot, one that impacts millions of employees at a critical moment.
How is When’s approach differentiated, and what excites you most about the future of the company?

When is differentiated in our approach as a B2B solution that integrates our health insurance marketplace directly with the employer, and we’re a fully licensed agency in all 50 states. We don’t just educate or offer options, we intervene at the exact moment risk shows up, when an employee experiences a qualifying life event, and guide them to the best individual coverage for their situation. That’s a fundamentally different approach than traditional COBRA or consumer-facing navigation solutions, which tend to be passive and too late. We’re solving a problem that employers have largely accepted as unavoidable, high-cost claims at predictable moments.

What excites me most is how early we still are. We’re just getting going! Employers are just starting to recognize this as a real lever to improve plan performance, and once they see the data, it’s eye opening. We’re building something that can meaningfully reduce costs for employers while also improving outcomes for employees at critical moments in their lives, from a job transition to Medicare eligibility. It’s a powerful combination and a unique win-win for employers and employees.

When focuses on what happens after someone leaves a job—something most companies historically haven’t prioritized. Why do you think the end of the employee lifecycle has been such an overlooked part of the benefits experience?

I think we spent our first year working on When talking to as many people as possible, assuming there was no way this problem had been overlooked. We figured we’d find an existing solution and move on. But nobody was really addressing the end of the employee lifecycle or helping with coverage transitions. Sadly, we heard this phrase frequently (still do at times), “I don’t care about employees after they leave the company.”

For whatever reason, most employers have just accepted the status quo of offering COBRA, even with the ACA and the continued rise in employer healthcare costs. It’s a major blind spot, and one that’s unique to the U.S., where most people get coverage through their employer. Because of COBRA, employers can still be on the hook for former employee claims for up to 18 months after they leave. We’re shining a light on the claim risk COBRA participants present to employers, like they generate 15x more million-dollar claims than active employees. The claim data and our innovative solution is making the forgotten part of the employee lifecycle a priority.

What is your superpower?

I like to say I’m pretty good at handling the rollercoaster ride of a startup. I think I’m pretty good at handling its highs and lows. I love the speed, the thrill of climbing the unknown, the twists and turns, and I don’t get too nauseous on the big drops. I think I’m just wired for it. Ironically, as I’ve gotten older, I need Dramamine before going on actual rollercoasters with my kids or I’m a mess afterwards.

Are there any specific books or podcasts that have had a significant impact on your personal growth or leadership style?

I haven’t listened to it recently, but I’ve gone through a lot of How I Built This episodes over the years for inspiration, clarity, and motivation. I’m sure those stories and lessons have influenced how I think and operate.

For entrepreneurs working on big systemic challenges – like healthcare, insurance, or workforce benefits – what advice would you give them about where to start and how to stay resilient?

It all starts with discovery. Drop any preconceived ideas about the solution and spend your time getting buried in the problem. Talk to as many people as you can who actually experience it, not just the buyers, and look at it from every angle. Some of the most valuable insight will come from people who don’t even think it’s a problem, spend more time with them.
Dan and I joke that if we knew how hard this would be, we never would’ve started When. Sometimes a little ignorance is helpful. You have to be ready for people to dismiss your idea, buyers, investors, even friends and family. It sucks but that’s a part of it. And honestly, the naysayers can be the most valuable. Early on, pre-revenue, we had an employer turn us down. Instead of moving on, we dug in to understand why. Based on their feedback, we scrapped nearly two years of work, rebuilt the When Benefit product, and ended up launching one of the most effective severance solutions in the market.