The Flexspring Podcast

Dean Carter spent 25 years as a head of HR at Fossil, Sears and Kmart, Patagonia and Guild. Then he took his first CEO job, at an AI company, at 60. In this conversation he walks through the career logic behind all of it, and the advice he gives young people more than any other: stop optimizing for salary in your twenties.

Dean Carter is the CEO of Instill, an AI company that coaches teams on culture and performance while they are actually in the meeting. He talks with Yan Courtois about how the great retail talent pipelines were built and then lost, what he looks for when hiring into AI roles, and why he is building AI to protect jobs rather than remove them.

Key topics:

- Learning years vs earning years, and the salary trap in your twenties

- What happened to the department store merchant pipeline, and why it matters now

- Hiring for hunger, gratitude and curiosity over technical star power

- An AI coach in the room, not a report three months later

- Camelot moments: leading a team when the company is going under

- Why 60 is a beginning, not an ending

Chapters:

00:00 Meet Dean Carter, 25 years in HR
02:14 Fossil: watches in a tin can, and a global ride
04:27 Running HR for 2,000 people with a team of two
06:22 The talent pipeline that dried up
11:55 What centralizing did to Macy's merchants
13:40 Using retention data to pick which schools to hire from
16:31 Learning years vs earning years
18:11 Selling diapers to nursing homes at P&G
21:02 Spotting HR at 24 as the job nobody wanted
22:00 Turned down by Disney, Nestle and IHOP
23:45 Arrows in your quiver, and the boss everyone avoided
26:20 From CHRO to CEO of an AI company
27:50 Putting an AI coach in the room while the team meets
31:55 Hiring hungry, grateful and curious
33:38 Building AI to save jobs, not cut them
34:28 Camelot moments and the band on the Titanic
38:37 Why 60 is a beginning, not an end
41:30 The question every CEO should ask every day
44:51 Why he is a big believer in interns

Follow Dean Carter:

LinkedIn: https://www.linkedin.com/in/deancarter/
Instill: https://instill.ai

Follow Yan Courtois:

LinkedIn: https://www.linkedin.com/in/yancourtois
Flexspring: https://flexspring.com