On the Podcast: Andy Hamilton Talks COBRA, AI, and Building When

Life’s a Pitch (podcast)

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May 1, 2026

CEO Andy Hamilton sat down with Jared Gibson on Life’s a Pitch for a 35-minute conversation about what happens when people leave a job, and why so few companies think it through. Andy also shares the personal story behind founding When, drawing on his own experience navigating healthcare during the pandemic.

Highlights from the episode

• Most companies invest heavily in recruiting and onboarding, but few think through what happens when an employee leaves - even though departing employees often stay on the company plan through COBRA and drive up costs.

• Andy talks candidly about how his own experience during the pandemic shaped the decision to start When.

• Why healthcare shopping is confusing for almost everyone, and where AI and concierge-style human support work best together.

• The shift from founder-led sales to a professional revenue organization, and why startups keep rewriting their messaging while searching for product-market fit.

• The personal side of entrepreneurship: the emotional highs and lows, parenting, and staying grounded.

Are you ready for When?

Curious what better offboarding and COBRA support looks like in practice? See how much you could save with our COBRA Savings Calculator, or schedule a demo to see the platform in action.