Andrea Cooper, Chief Officer at Talkspace: Surround Yourself With People Smarter Than You

Andrea Cooper is Chief People Officer of Talkspace. She grew up in a small town in Kentucky, one of five children in a family without much money, where nobody talked about work and the words "human resources" were never said out loud. She started at Walmart at 19, a full-time student at the University of Kentucky on her way to becoming a social worker, supervising cashiers for about $5.25 an hour. Her store manager asked what she would earn out of college. Seventeen thousand, she said. He told her the management training programme would pay thirty. She called her mother, who said she would support whatever Andrea chose, and also that in her experience we adjust our lifestyle to match our income. Andrea quit school and became an assistant manager trainee. The next few years were muzzleloaders out of sporting goods, mixing paint and unloading trucks overnight. Then a leadership training session in the back room of her own store, where she watched the trainer work and thought: I want that guy's job. That was the first time she could see a path. She stayed at Walmart twenty years, leaving as Senior Director of HR. Along the way she ran HR for the health and wellness division of more than 50,000 people, built a global sourcing function across roughly 25 countries that had not existed before, and finished in diversity and inclusion. Then an Amazon subsidiary in Madison, three and a half years working for herself, and a talent leadership role at a Madison financial services firm. The recruiter's message arrived on LinkedIn. Talkspace was a full circle she did not expect: the 19-year-old social work major, now leading the people function for a mental health company. She joined in 2022, shortly after the company went public, into a declining stock price and a reduction in force inside her first two months. Talkspace was acquired by Universal Health Services in August 2026. In this episode, Andrea tells Tiffany Pham what her mother said about money, what losing the fear of being fired actually did for her, why she can no longer zip up her corporate suit, and the advice she gives anyone who wants her job. Chapters: 00:00 Welcome 00:46 Before the chief officer seat 01:05 Origin stories, and why corporate ones are not the whole picture 01:21 A small town in Kentucky, five kids, no talk of work 01:42 Walmart at 19, and a social work degree in progress 02:06 The store manager's question 02:47 Thirty thousand dollars a year 03:15 Her mother on lifestyle and income 04:01 Muzzleloaders, paint and overnight trucks 04:27 The training room, and "I want that guy's job" 05:10 Her first foray into HR, which Walmart called the people team 05:31 Twenty years, up to Senior Director of HR 05:53 HR for health and wellness, 50,000 people 06:16 Building global sourcing across 25 countries 06:38 Her last Walmart role, in inclusion and belonging 07:16 Why leading teams is her favourite part of the job 07:42 Surround yourself with people better than you 08:31 Was the opportunity given, or did she go after it? 09:22 Moving every two to three years 10:00 Leaving in 2015: Amazon, then working for herself 10:43 What stepping away from a paycheck took 11:09 Losing the fear of getting fired 11:57 Tiffany on where her own entrepreneurial streak came from 13:05 Why she went back into a corporate setting 13:51 "I can't zip up my corporate suit anymore" 14:42 The job in between, and the call from Talkspace 15:35 A 19-year-old social work major, all these years later 16:48 Mogul and Talkspace as startup neighbours 17:14 The call, and the first person she told 18:20 A first week that was not sunshine and rainbows 18:42 A reduction in force inside two months 19:36 Coming out the other side 20:02 Tee, and AI with a clinician behind it 21:05 Her advice: don't follow my footsteps 21:31 The people you surround yourself with 22:16 Close Quotes: "I never really knew what corporate was. I wouldn't have even known the words human resources." "She said, in her experience, we adjust our lifestyle to match our income or our means." "After that I was like, okay, I want that guy's job. And suddenly I could see a path for myself." "Surround yourself with people smarter than you, better than you, more capable than you." "I had been carrying this fear: what if I got fired? Working for myself took that away. If it happens, I'll be fine. I can figure this out." "I can't zip up my corporate suit anymore. It just doesn't fit me anymore." "Here I was a 19-year-old social work major barely getting by. To be leading the people function for a mental health company all these years later is the dream." "Don't follow my footsteps. Figure out your own path." "That whole ecosystem of people that you surround yourself with makes you better if you let it." Listen on Spotify, Apple Podcasts or Amazon Music, all from one page: https://share.transistor.fm/s/d7832a9c More from Mogul: https://onmogul.com Chief Officer, all episodes: https://onmogul.com/podcast