“I've had people tell me, ‘Oh I've heard it’s unlimited vacation and you get to work from wherever you want. The tip is ‘Have a good why!”, says Matthew.

Matthew describes his journey from a successful State Farm agency to joining the team at Obie, satisfying his entrepreneurial desires.

Headquartered in Chicago, the property insurtech caters for time poor landlords, entrepreneurs or small business owners, offering a flagship product in the 1-4 unit rental space.

In the midst of a Series B funding round, Matthew explains, “We’re doing it out of the want to grow and not out of the need to survive, which I think is key.”

Matthew highlights the ambitious growth plans for 2023 and discusses the challenges of inflation, rising interest rates on the property rental market and the plans for building its customer base in tough times.

Sharing his interview tips for candidates looking to join an insurtech, Matthew says, “I love when someone asks for the role and tells me, ‘You'd be disappointed if you don't bring me on.’”

He explains the family culture at Obie and the team’s desire for people to connect on that level as the business seeks to add up to 50 roles in the next 12 months.

Matthew concludes by sharing the other insurtechs he admires, “I don't have a poor word about any of them, they're pioneers. Whether you're insurtech 1.0 with Lemonade and Hippo, we wouldn't probably be here without them.”

Connect with Matthew on LinkedIn or find out more about Obie  

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

Copyright Insurance Search 2022 – All Rights Reserved.