January 2016 – Shai and I might have been suitable founders for Lemonade, an insurance company, except for one glaring snag: we knew nothing of insurance. Not a problem, we reasoned, all we needed to convert our harebrained concept into a licensed insurance carrier was to hire the A-Team of insurance.

That’s when we hit snag #2.

Finding insurance natives to guide us through the regulatory, financial, actuarial and reporting maze proved hard enough for us tech natives. But we soon realized we needed more than that. We were looking for insurance ‘insiders’ who were simultaneously ‘outsiders’, able to question and challenge the foundations on which they built their career. In other words we were looking for an oxymoron. A paradox. A unicorn.

Well, pursuing unicorns is what we signed up for.

I psyched myself up by pretending I was Hannibal from the A-Team (a childhood fantasy I haven’t entirely outgrown). I told myself that like him I was looking for people with extraordinary skills, trained by the best, yet they also had to be odd-bods, nonconformists who were never fully domesticated by the machine. I didn’t expect to find folks who were dishonorably discharged from the US Rangers (how cool would that be!), but at a minimum, I wanted people in the throes of a midlife crisis.


Lemonade Company Job Requirements

Today we announced that our insurance A-Team includes the former President of Product at AIG (our Chief Insurance Officer, Ty Sagalow), Senior Vice President & Chief Underwriting Officer at ACE (our Chief Underwriting Officer, Rob Giurlando), ACE’s Senior Vice President of Claims (Jim Hageman, our Chief Claims Officer) and AIG’s Head of Financial Planning and Analysis, P&C (our CFO, Ron Topping).

Their highfalutin’ titles, bestowed upon them by Big Insurance, makes them sound buttoned down, staid, tame. Institutionalized even. They’re anything but. This motley crew bears the scars of decades of fighting the good fight. If I’d endured what they’ve been through you’d find me at the bottom of a bottle. But not this gang. They’re channeling their angst to remaking the industry, pouring their century of combined experience into Lemonade.

Are they a little crazy leaving the corner office for the life of a startup? I hope so. We like ’em a little crazy. At any rate, we’re now a team, A TEAM, and we’ve got our marching orders: our mission is to remake insurance as instantaneous, un-conflicted and downright delightful.

I love it when a plan comes together.