S4 EP13: Practising your craft in an unencumbered culture – with Tom Schmitt, Chief People and Administrative Officer, Skyward Specialty Insurance

“Cultures are not just based on what we measure and how we reward, but they’re based on storytelling. At the end of the day, a culture is really just ‘what do we care about and equally what do we don’t care about’”, says Tom.

“We don’t care about bureaucracy, we don’t care about hierarchy, we don’t care about titles. We do care about creating an empowered organization, where everybody can bring their true authentic self to work.”

Tom shares his journey, from being in HR his entire career with roles in banking, high tech and insurance to joining the Skyward team in June 2020. He highlights the contribution he has made from the company rebrand to the first successful IPO of 2023, all supported by the passion, enthusiasm and vision of CEO, Andrew Robinson.  

“We had the opportunity to build the company we always wanted to work for. I’ve worked for large companies, small companies are a lot more fun. It’s like it’s like being the captain of a speed boat versus the captain of an aircraft carrier. We can turn on a dime.”

Tom discusses the IPO process and its impact across the organization.

“It’s been a tremendous boost to all of our staff. We shared in the celebration with our entire team. Every single employee received equity in the company as part of the IPO”

Tom talks about building a wining culture and cascading information and key objectives to the entire team in a consistent way.

“What that means is every single person understands what they need to do in order to contribute to the success of Skyward Specialty.”

He emphasizes how hiring is based around hiring in the model of the ‘go forward’ organization, where people can truly practise their craft.

“People don’t want to be encumbered by a bunch of bureaucratic rules. Super accomplished individuals – whether that’s underwriting, claims or the various support functions – want to be able to bring their expertise. They want their ideas heard, they want to be able to contribute.”

Tom highlights Skyward’s approach to hiring exceptional talent and encourages applicants to know that interviews are a two-way process.

“I always encourage candidates to interview us and understand if this is the right environment. We give candidates an opportunity to meet a number of different people and ask the same question to different people and see if they get the same answer.”

Tom concludes by sharing an interview experience that has stuck long in his mind.

“Education, skills, competency, that’s table stakes. Character, drive, work ethic and never ever giving up is what wins the day. And that’s what we look for in candidates.”

Connect with Tom Schmitt on LinkedIn or find out more about Skyward Specialty Insurance

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

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