17 | Scaling Culture from Scratch: A Conversation on Building Trust & a Business That Lasts with Tom Hickey
Update: 2025-08-25
Description
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
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