Surround Yourself With People Smarter Than You

Tiffany Pham

Hi, Andrea. How are you?

Andrea Cooper

Good. Thanks, Tiffany. Thanks for having me.

Tiffany Pham

I'm so delighted to have you and super excited for everyone to hear your story. I just find it such a delight to talk with you each time. So really excited for this.

Andrea Cooper

Thank you. Me too. I'm excited to just have the conversation. You are such a, I don't know, like somebody to look up to, a model of entrepreneurial ambition and success. It's so cool.

Tiffany Pham

Thank you, Andrea. And, you know, I wish everyone could see you right now. My favorite joke to Andrea is to say to her that she looks exactly like Zooey Deschanel. So if you're not watching, you're only listening, you're missing out, because you would see on screen she looks like...

Andrea Cooper

Well, I object to that assessment, but I'm also flattered. So thank you.

Tiffany Pham

Wonderful. I'm excited to get to hear your story. So I'm excited to just hear from you about your incredible journey prior to your Chief Officer role. And then of course we'll dive into that role itself shortly, but excited to hear about where you grew up and how you grew up and the journey that you undertook before that Chief Officer role.

Andrea Cooper

Yeah, thank you. So it's funny, I was at a conference about a week ago and I knew we were going to have this conversation. Something at that conference really stuck with me, which is people were talking about their origin story, and they were talking about it in terms of corporate origin. And it really resonated with me. So I was thinking about my origin story. I grew up in a small town in Kentucky, in a pretty religious family, but also a big family. I have four siblings, and didn't grow up with a whole lot of financial means. And so I don't recall my parents really ever talking about work. My dad was a salesman, my mom stayed home and took care of us. And so I never really knew what corporate was. I wouldn't have even known the words human resources. That would have been a completely unheard of concept to me. And so when I started at Walmart when I was 19, I was a full-time student at the University of Kentucky at that time and I was going to be a social worker. I was super excited. And I think I shared with you before, Tiffany, that my store manager came to me. And at this point I was a front end supervisor, so I supervised the cashiers, and I don't know what I made, but call it probably $5.25 an hour is my guess.

Tiffany Pham

And that's $5.25, just for clarity.

Andrea Cooper

And I was talking to my store manager and reminding him that I needed to go part time for my practicum in my degree program. And he asked me, he said, how much are you going to make when you get out of college? And I was like, probably 16, $17,000 a year. And just for those listening, if you can't see me and realize my age, this was in the mid-90s. So many, many years ago. But he said to me, well, did you know if you decided to do the management training program at Walmart and became an assistant manager, you could make like thirty thousand dollars a year. And I will never forget that moment. I think I was twenty at that point and I'd been working at Walmart probably a year-ish. And I went home, called my mom and just was gushing about, can you imagine what it would be like if I made thirty thousand dollars a year? I was salary. I wasn't counting on every hour and doing the math and thinking about how will I get gas, how I'll pay my rent, how I'll pay my tuition. All of that goes away. I'm making $30,000 a year. I'm set. And my mom, being the loving, practical mother that she is, she said, you know, I support whatever you think is best for you. I'm excited if you're excited. And also, what she shared is, in her experience, we adjust our lifestyle to match our income or our means. And I was like, oh my gosh, I'm going to be fine. That's so much money. Don't even worry about it. So I proceeded to quit school, became an assistant manager trainee, did the whole training program. And I was an assistant manager for a few years and it was hard. I'm not going to lie. It was very different than the life I had imagined for myself as a school social worker. I was carrying out muzzleloaders from the sporting goods department. I was mixing paint, I was working overnights, unloading trucks. It was just really hard physically and mentally, and just so different than how I had imagined my professional life to be. And I remember there were moments that I definitely thought, yeah, my mom was right. I have a car payment now, I have a nicer place to live with higher rent now. It all kind of changed in that way. But anyway, so I went to this training program and it was for leaders at Walmart, and I don't remember exactly the content other than it was leadership development and it was in the training room in our store. And after that I was like, okay, I want that guy's job. And suddenly I could see a path for myself, right? I knew that being a retail manager long term just wasn't going to be the right fit for me, but I also didn't want to feel like I had made a mistake and I didn't know how to restart. And so seeing that person training others, investing in others, and really connecting with people really gave me hope. And so fast forward a couple of years later, I was able to pursue a trainer job. And that was my first foray into HR. And again, I probably still didn't know the term HR, because at Walmart we just called it the people team. I didn't know human resources was a thing. But I knew I wanted that job. And I moved from Kentucky to North Carolina to be a regional trainer for other managers. And that really kind of began my true enjoyment and joy in working in HR. Through the years, I was with Walmart about 20 years.

Tiffany Pham

20 years, wow.

Andrea Cooper

Yeah.

Tiffany Pham

And you rose throughout your time at Walmart?

Andrea Cooper

Yeah. There was that trainer role, the step out of being a retail assistant manager. By the time I left, I was the Senior Director of HR. And I did different roles. I would say probably the biggest roles in scope: I was the head of HR for the health and wellness division. So that's the pharmacists, the vision centers, that part of Walmart. So, I don't know, 50,000 plus employees in that space. And then I would say the most complex opportunity I had at Walmart was in global procurement, the global sourcing division. That was an opportunity to build a division that didn't exist at Walmart and to then hire and develop people across, gosh, I don't even know, we were like 25-ish countries at the time. And so those are just two of my favorite experiences. And then the last role that I had at Walmart, I was a leader in the diversity and inclusion area. And I know it's not something we hear a lot about right now, right? This inclusion and belonging.

Tiffany Pham

They'll come back probably in some way.

Andrea Cooper

It will, it will. And to be honest, I'm not convinced it's gone. I just think it's gone underground, because it matters, right? It matters. So to do a job like that, where it's truly all about inclusion and belonging and thinking about the benefit of diverse talent and what that means to the org, it was a good note to leave on, right? After all those years with Walmart. And I would say the other thing that I found I loved during that 20 years: I really love leading teams. It was really fun to lead. I mean, sometimes they were small teams, but sometimes they were global teams, sometimes they were bigger teams, but no matter the scope or the number of people, it was just so much fun. There was this cultural value I picked up on in early days at Walmart, and I don't even remember the leader who said it, that you should surround yourself by people that are smarter than you, better than you, just more capable than you. And I took that sincerely to heart. And now fast forward to Talkspace, never has it better been illustrated in my career than that. I have the most intelligent, creative, scrappy team. And they're always smarter than me. And I feel really grateful for that. So yeah, leading is definitely one of my favorite parts of HR.

Tiffany Pham

That's amazing. Just to chime in on what you just said, I think about that a lot, about how people share, there's that popular quote that you're the average of the five people you hang out with.

Andrea Cooper

Oh yeah.

Tiffany Pham

So I always think about that, like, oh, who are my five? And am I the average of them? I think so.

Andrea Cooper

Yeah, they're raising my average. I feel like, again, when you surround yourself with really smart, creative, resourceful people, it just makes you better.

Tiffany Pham

Yeah, absolutely. I do have a question about your Walmart days. When you were training people, was the opportunity given to you, or did you have to go after the opportunity to move into corporate?

Andrea Cooper

That's a great question. It wasn't just given, no. It was definitely something I had to, you know, in a big company, you have to learn to figure out how do you get information. And it took a little time, right? Like I said, it probably took a couple years of me being an assistant manager in different stores, and then asking, and I don't remember if it was my district manager, I don't recall how I finally figured it out. Walmart has a really strong culture of internal opportunity and internal promotion. And so they post all their openings. So I would have been looking at the intranet and finding that opportunity that led to the interviews. So yeah, it definitely wasn't given. It took some resourcefulness on my part to figure it out. But I will say that in that twenty years, probably every two to three on average, I was moving into a different role, often up, but sometimes across as well, just to continue to build out the areas of passion I had within HR: talent, diversity, and then obviously just that business partner space. But I think that you had to pursue it, but it wasn't too hard, because there was an openness and an invitation to continue to try new things.

Tiffany Pham

Amazing. Were you somewhere in between Talkspace and Walmart?

Andrea Cooper

Yeah. Let's see. I left in 2015, and as much as I learned and grew in those 20 years, I would say that in the 11 years since I've left, I've grown so much more. I think that's just the diversity of experiences that I've navigated. I left Walmart, I went to work for an Amazon subsidiary in Madison, Wisconsin, which is where I am. We love it here. And after I left Amazon, I decided to work for myself and did that for about three and a half years. And I'm just going to say, being a corporate girl my whole adult life, stepping away from a regular paycheck took a ton of nerve on my part. It was not natural. But once I got into it, it felt so energizing, and I met some amazing people, different entrepreneurs and different consultants. I realized that all those years of diverse experience let me say yes to a lot of projects from a consulting perspective, so I could continue to be scrappy and get business. And it was really fun. Really hard, I'm not trying to sugarcoat that, like, oh, I was amazingly successful, I never had any struggles. No. But I learned about myself, and I realized I think I had been carrying this fear of, what if I got fired? Especially in a big corporate, you do a lot of RIFs, a lot of layoffs over the years, and I often was in charge of executing on those things. And so I always had carried this, oh my gosh, what if that happened to me? And I think that working for myself those years took away most of that fear. It's like, if it happens, I'll be fine. I can figure this out.

Tiffany Pham

Yeah. That's such a blessing that you figured that out. I love that. I actually rarely hear someone else outside of my own family talk about that.

Andrea Cooper

Really?

Tiffany Pham

Yes, it's so wonderful to hear you talk about it. It just reminds me how my own father, growing up, part of why we kind of had entrepreneurship instilled in us as children across my family, was because my father used to always talk about that, like in corporate America and how there's always this trust you had to put into others that really maybe wasn't well deserved necessarily, and that the person you could most trust was in yourself. And so therefore, that's why he always vouched and advocated for entrepreneurship.

Andrea Cooper

You're lucky. You're lucky. Your origin story in that way is so amazing, because I didn't know that, right? And I grew up kind of in all these systems, right? I mean, whether it's public school, whether it's church, whether it's work, you kind of abdicate some of that ownership. You follow the rules, you accept that this is the reality. And it was terrifying to me to think that that wasn't going to be the case. But also, going through it made me realize, okay. I have three kids, they were school age, like elementary, and I was like, ooh, this is really hard to balance all this. And so when the opportunity came to be back in a corporate setting, it felt strategically smart. It felt like an opportunity to lead a team again, which I really missed. But I will never forget that that's an option for me, right? And I don't know at what point in my career I will go, you know, that entrepreneurial spirit, I think when you have it, it doesn't just go away. So yeah, you're really lucky that you had that learning early in your life. And I'm really glad I got it eventually.

Tiffany Pham

Yeah, and it probably makes you a better leader now today in corporate, like you said, because now you don't have that potential kind of subconscious underlying fear or anything like that. Everything you do is for the betterment of whatever you're doing, because you have that feeling of freedom probably, that you can always rely on yourself if needed.

Andrea Cooper

That's a good way to say it. I think you're right. I've said to friends before that I can't zip up my corporate suit anymore. Like, metaphorical suit, not real suit, right? I'm definitely not wearing heels or a suit anymore. But it doesn't fit me anymore. And there's times that I try, right? Because I know I should in a certain setting, but it just feels so, it just doesn't fit me anymore. And I think it's what you just said. It's because I want to do things for the reasons that align with my values and that make employee experience better and support my team. But I'm not necessarily motivated or inspired by, do it because this is the way it's done, or this is what you're supposed to do to get by and succeed in a corporate culture.

Tiffany Pham

Exactly. No, absolutely. And so was it then, after your entrepreneurial journey, that was the time that you got the phone call to join Talkspace? And how did that happen? Was there a role before Chief Officer?

Andrea Cooper

Yeah, sorry to interrupt you. So there was one job in between. So I worked for myself, and then in doing that work and being on panels and speaking, I made some good contacts. And there's an organization here in Madison, a financial services insurance organization, and they were looking to create a leader for their talent function. And that was recruiting and succession planning and leadership development. Their CEO was retiring in a couple years, so it was a really fun opportunity to really say, what's the plan for the future of the org? So I did that. Actually, that's where I was when I got the phone call. And candidly, it was just one of those random phone calls. I think the recruiter maybe started with a message on LinkedIn and then I replied, and I did a little research on Talkspace. I listen to a lot of podcasts, so I definitely was familiar with Talkspace. And it felt like this full circle moment. I think I shared this with you before. It was like, okay, here I was as a 19-year-old social work major barely getting by, but I really loved the work of social work. I love that impact that it makes. And then to be able to have an opportunity all these years later to be leading the people function for a mental health company is just the dream, right? Being able to do work that really matters, beyond just the nice to work with people stuff, but the stuff where really people's lives are getting better, has been really fun. I don't know candidly why that recruiter thought that, hey, Andrea might be the right fit. I think probably it's a combination, right, of the Walmart experience and all the things we've just talked about, that I could probably navigate a scrappier health tech company and would be able to be successful there even if a lot of my time had been in a very large Fortune 500 company. I appreciate that recruiter. Not every recruiter would think that.

Tiffany Pham

Yeah, I appreciate that recruiter as well. I do see it as, obviously Mogul as executive recruitment amongst other things that we support on, your background is the perfect melding for making you the right leader for Talkspace. And full circle moment for me. Actually, I should share with listeners today, it's really fun to become friends with Andrea, because actually earliest days of Mogul were spent in the same headquarters building as Talkspace. They were our neighbor, and we were the two kind of, a decade and a half ago, startups that were taking off across the floor. And so it's really fun and full circle to be friends with Andrea now, who leads Talkspace. So yeah, excited. And so what was that moment like when you got that phone call that you were the one selected, that you were going to be able to join as the chief officer? Who did you call? What was that moment like?

Andrea Cooper

Oh, yeah. I haven't thought about that for a while. It was exciting. I was also super nervous, because I wasn't sure, can I really do this job? Would I be able to be successful in this role? Going back to my Walmart story, of course, the first person I call is my mom. And we talk it out. And that always makes me feel grounded and calm and like I can do this. And then being able to share with friends. I would say that a number of my friends, as they found out, were like, yeah, this makes sense. This aligns with you. And so that was a huge compliment to me too, that people would feel that those kind of values of Talkspace and my personal values would go well together.

Tiffany Pham

I love that. And so what was your first week like?

Andrea Cooper

Oh, it wasn't easy. I make it sound like sunshine and rainbows right now, but the reality is the business was struggling at that point. I mean, the company was public, had been in the last year-ish. I don't remember exactly, because it had just gone public pretty recently when I joined in 2022. And business was not great, or not meeting plan. I shouldn't say it was bad, but it was in growth mode. We were really stretching, kind of that post-COVID world of how employers were thinking about providing mental health benefits to their employees was shifting, and our stock price was declining. So there was a lot of really tough things. Within my first two months we had to do a pretty significant reduction in force, which I didn't know was going to be on the path so soon. But all that to say, there is something very satisfying and meaningful when you get through those really rough moments with my peers, who are now my friends, my colleagues, and we see it on the other side. We get through, we fight hard for the business, and to see the outcome of that has been really good. But it wasn't all sunshine and rainbows the first week or two or a couple months, candidly.

Tiffany Pham

And you led it to rainbows and sunshine, maybe, right? Like now you've gone through an incredible exit and you're at an exciting moment of the company journey.

Andrea Cooper

True, that's really true. Yeah, and it's really fun to see that, right? And selfishly, what a great experience as an HR leader to be able to go through that learning curve, because it is a learning curve. I'm learning a lot, and now being part of a large public company, it's a different full circle moment, right? I'm kind of being back in that space, and lots of learning, lots of personal and professional growth, and I'm really grateful for that.

Tiffany Pham

And is there anything you're excited about in the years ahead for AI, the future of work?

Andrea Cooper

Oh, definitely. I would say we have a new AI tool called Tee. It's funny that you know Gil from your days back, our chief technology officer, and he and his team have built a new AI tool, and it's just really exciting. It's that opportunity for people to have touch points in between their therapy, or maybe to be able to have an entry point before they're ready for therapy. And just seeing that tool, and it is all supervised by our clinicians, so kind of having real humans that are licensed therapists part of that tool, I think is really exciting. And again, it's exciting because it's another opportunity for people to be able to get help for themselves, get support for themselves in the way they're ready. So yeah, lots of exciting stuff. It's never a dull moment around here.

Tiffany Pham

Amazing. And what's your final advice for someone who's looking to follow in your footsteps and become a chief officer themselves one day?

Andrea Cooper

Thanks, Tiffany. Well, I would say don't follow my footsteps. I would say figure out your own path. And I don't mean that in a cliche, silly way, but truly, I think I spent a lot of my career, early in my HR career, trying to follow and trying to find, okay, how do you do this? What's the next step? And ultimately, what I've come to believe is that finding what aligned with my personal values and my professional aspirations meant I had to chart my own course, right? So I would say the advice I would give is, really the people you surround yourself with makes all the difference. And it doesn't need to just be people that are mentoring you, it's some of that. It can also be people that are early in their career and reporting to you. That whole ecosystem of people that you surround yourself with makes you better if you let it, and probably helps lead you to follow the path that is best suited to who you are as a person.

Tiffany Pham

I love that. And I feel like your journey beautifully exemplifies that. So thank you so much again for your incredible and inspiring story today. It was such a pleasure to talk to you, as always.

Andrea Cooper

Always so much fun. And I feel like we resonate so much because of similar values and life paths. It's always a wonderful time.

Tiffany Pham

So thank you again, Andrea.

Andrea Cooper

Thank you so much for the opportunity.