Changing behavioural psychology from head to toe – with Jon Cooper, CEO & Co-Founder, Overalls

“I realised that big company culture just wasn’t for me. I operate best in the start-up space”, says Jon.

The lifelong entrepreneur and insurtech pioneer talks about launching his second business Overalls, after selling Life.io in 2021.

An early stage business with a current team of 10, Overalls is reinventing workplace protection and changing our psychology and attitude towards insurance. Through its three-pronged product offer – Hassle Helpers, Mighty Moments and Pocketbook Protector – Overalls is helping employers and their people reclaim the time, money and joy that are often lost to life’s hassles.

“It allows us to engage people at the moments that matter most and help position the right insurance products for them at that time”, says Jon.

Jon shares how access to capital and a team of culturally aligned, experienced entrepreneurs is providing a solid platform from which to scale, but highlights how cracking the code of remote-working keeps him up at night.

“We’re trying to figure out how we allow people the freedom to be independent, while maintaining that culture and connective tissue on the team.”

Jon discusses future growth plans, T-shape leadership and maintaining values as the business scales, highlighting the transparent culture from top to bottom and the weekly ‘show & tells’.  

“It gives you a window in to what everyone else is doing and how it fits together.”

Jon talks about access to talent, the value insurance knowledge brings to the team and work-life balance, as well as how infrastructure is allowing insurtechs to launch and build quickly.

In conclusion, Jon gives his thoughts on the common misperceptions of being part of a large business versus a start-up.

“People underestimate how risky it is being with a larger company. There’s a randomness to things outside of your control.”

Connect with Jon Cooper on LinkedIn, email jon@overalls.ai or find out more at www.overalls.ai  

The Insurance Coffee House Podcast is hosted by Nick Hoadley, CEO, Insurance Search, the Executive Search Consultancy for growing Insurance and Insurtech businesses across the globe.

To discuss identifying & attracting the very best talent to your team or being a podcast guest, reach out to Nick via nick.hoadley@insurance-search.com or connect on LinkedIn

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