17 | Scaling Culture from Scratch: A Conversation on Building Trust & a Business That Lasts with Tom Hickey

In this episode, Jess talks with Tom Hickey, CEO of Wedgewood Insurance, about the messy, meaningful work of leadership. From scaling a team without a playbook to building trust that sticks, Tom shares what he’s learned his decades-long career. Leading with heart, staying curious, and figuring it out one honest conversation at a time Chapters (00:00:00) - Unlocking Your People: Leadership and Culture(00:01:29) - Tom Munn(00:02:25) - Wedgwood CEO on People, Culture and Leadership(00:09:02) - How to Ask the Lead Why They Want to Lead(00:12:41) - In the Elevator With Steve Jobs(00:13:13) - What are some of the pitfalls of new leaders?(00:19:27) - Small Businesses and the culture(00:24:21) - In the Elevator With Businesses(00:24:45) - Getting People to Believe in Their Values(00:26:56) - How Do You Ensure a Good HR Team?(00:31:09) - Employee Relations: The Role of HR in a Company(00:36:22) - Jess on Self-Advancement(00:38:06) - Question of the Day(00:38:32) - How Do You Build a Remote Company Culture?(00:40:46) - Leadership With a Lead(00:41:51) - Is culture part of the business?(00:47:17) - Working Remotely