What I've Learned (So Far) From Being A 3-Time CMO & First-Time Mom

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This is a podcast episode titled, What I've Learned (So Far) From Being A 3-Time CMO & First-Time Mom. The summary for this episode is: Tricia Gellman is the host of CMO Conversations, and on this episode, she’s also the guest. At the end of 2020, Tricia went on maternity leave to welcome her daughter into the world. But now she’s back at it and figuring out the balance of being a new mom, wife, and – you guessed it – CMO. She’s joined by Dena Upton, Drift’s Chief People Officer, for a candid discussion about her journey to motherhood, her transition back to work, and what she’s learned so far. Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends. You can connect with Tricia and Vidya on Twitter @triciagellman @heydenaupton @DriftPodcasts -- Tricia's Article in Business Insider --> I'm a 3-time CMO and 5-time ironman triathlete, but having a child is the hardest thing I've ever done: https://www.businessinsider.com/drift-cmo-tricia-gellman-motherhood-infertility-ivf-loss-career-2020-10 The Rainbow Fish by Marcus Pfister https://bookshop.org/books/the-rainbow-fish/9781558585362 Big Words for Little People by Jamie Lee Curtis https://bookshop.org/books/big-words-for-little-people/9780061127595

Tricia Gellman: Hey, everyone. Welcome to CMO Conversations. I'm Tricia Gellman, the CMO of Drift. And in this podcast, I interview CMOs. I try to publish every other week. And my goal is to talk to CMOs about what it's like to weather the storm of the changes that are happening for CMOs in the world, and also, to sort of look at what it means in my mind to be a CMO 3.0. And what I mean by that is that, as a CMO, you should be stepping up to be a leader that's adding value, not just for marketing, but across the organization, helping to bring everybody together and also taking ownership of revenue, not leads. So you may not have realized this, but in the past three and a half, four months, I have been on maternity leave. I worked my little butt off before I went on leave to do lots of interviews so that we could have podcasts running every other week while I was out, but now, this is my first episode recording while I'm back. And we've decided to do something totally different. And instead of me interviewing people, I have with me, Dena Upton, who's the chief people officer of Drift, and we're going to talk about my journey to motherhood and what it's like to be a CMO at a hyper- growth company and have a new little baby at home.

Dena Upton: Welcome back, Tricia. You've had quite the journey.

Tricia Gellman: Well, thanks, Dena. It's good to be back. I'm still adjusting, but it's going to be back.

Dena Upton: And you've been back for a month, which probably seems like a couple of years. How's the transition been?

Tricia Gellman: Yeah, I mean, I made the decision that I would literally shut off work when I went out on leave. And I just felt like this is a once in a lifetime thing to have these early days of my child's life. And it took us so long to get here, why would I try to work while I was also trying to figure out how to be a mom? And so, as a part of that, I kind of, in my mind, recognized that, as a leader, there will be a lot of decisions that were made that I would just have to kind of get on the bus when I got back, which I think is difficult because I'm used to being a big collaborator in those decisions. But I would say that was one of the trade- offs, is you have to sign up to the fact that you're just going to go along with your other leaders and you feel confident in the company that that's okay. But I just didn't feel like I could be engaged in the way I would want to be and be out. There was kind of one or the other. Coming back, it's definitely been really hard, harder than I thought it would be. One, it was just like," Oh, I spent all this time with this child and I've been wanting to have this child for so long, and then now I'm just going to see her like two to three hours a day or something," because they sleep so much. Yeah, so I think it's just been hard to trade- off the time, re- engage on projects. And then I think at Drift specifically, we're such a hyper- growth company, we have so many things going on, just even re- engaging in all the projects, finding the time to get up to speed, it's been a challenge.

Dena Upton: Did you ever, as you were sort of picturing coming back to work... You're a planner, Tricia, I know that because I know you, but you can't plan everything, right? You can't plan that maybe your child will have trouble eating. There's certain things you can't plan. How do you emotionally get over that? Because planning a child's schedule that you don't have complete control over, and especially as they're three or four months old, it's hard to do that. How do you manage it?

Tricia Gellman: Yeah, I mean, I think that actually, this is the biggest thing. I think in life, hopefully you're taking risks and you're putting yourself out there to do new things all the time to have this sort of continuing learning and growing experience in life, right? And grow your career, grow your experience level, fail in things and be okay with a failure. But I've found that in this baby thing, that you know there are these milestones, you know there's these things, but you don't know how you're going to feel when it happens. And so, we were really lucky to be able to hire somebody to help us in the first two months, and I kind of saw that as a way to invest in my marriage and my child's success. Some people were like," Whoa, that's really expensive to hire a nurse for the first couple of months," but I'm like," It's more expensive to go through divorce and to go through counseling, to be honest." So we had this other person. And I always knew we're going to have this person for two months and then, it's super expensive, so we're not going to have them. But then when it happened, I was like," Oh crap, now I have to be the leader. I have to step in and make the decisions and I have to do this stuff." And I found it really overwhelming. The same thing when I came back. I knew I was going to come back. I knew I would have to go through the challenges of saying goodbye in the morning and coming home and all of these things. But in the end of the day, once you do it, you start to feel what's happening. And it was hard at first because I didn't know what would bother me. And then I realized in the first week that I was having a hard time just getting up to speed with everything. And I had to realize, okay, what are the things you really need to get up to speed on and how can you prioritize those meetings and talking to those people? And then I also realized I wanted to be able to check in with the nanny to understand what's happening in the middle of the day. So maybe not be there, but at least get an update and get pictures. So I asked her to start sending me pictures and things. So I think it's just checking in with yourself and understanding what's really going on with yourself on a regular basis, and then being able to pivot.

Dena Upton: What made you decide to write the article that you did and you published in Business Insider, and what has the response been?

Tricia Gellman: Yeah. When I was talking to the team about being out on maternity leave, one the things that came up is just what a big deal it was for me to be having a kid. And I think people just think," Oh, you want to have a kid," you decide you're going to have a kid, it's like in the fairytales and the movies and it's so simple, but I started expressing my anxiety about it because it had taken so long. And up until the moment that we had our child, I kept thinking" It's still not going to happen, it's still not going to happen." And so I kind of was talking about it a lot to people and realized it's beneficial to me, but it's also beneficial to a lot of people to really talk about these stories. Because for so long in my journey to have a child, I felt really isolated and I was struggling with the fact that something's wrong with me. And it's because these topics of fertility and having a child when it's not working out a hundred percent are just kind of taboo, right? People don't talk about miscarriages, et cetera. But then when you start talking about it, you find, oh my God, there's so many people who have the same challenges. And so I wanted to create an environment where maybe if I put my voice out there, it would encourage other people to put their voices out there so we could stop this sort of taboo culture. It's somewhat working because there were people that I don't even know who saw... I posted about the article in LinkedIn, and then people posted back and I didn't know them. And they shared with me their own journeys, or they shared how they felt it was so important because they knew other people who had the problem. And I think that that's good. If I can feel like I helped a couple people, to me, that's really an awesome.

Dena Upton: Have you noticed any changes or differences in the way you approach your work, the way you lead your team or the way you consider kind of marketing in general because of the, well, the addition to your family and then the time that you've taken away from work?

Tricia Gellman: I don't know yet about any different way of thinking of marketing. I think with COVID, what I at first found is that, well, obviously you have to bring much more empathy into your marketing, into your leadership, into everything. And then I think it's very emotional having a child and not being there all day to see how they're developing and everything. And so maybe that's impacting... I think a lot of what we're looking at right now is our brand and what does it stand for? And we kind of rebranded the company look and feel before I left and a whole new category. And so I'm trying to figure out how do we make it resonate at an emotional level what we're doing and what our brand stands for. And I don't know that that's really being influenced by the emotional component of having a child or if it's just really where we need to be. Yeah, so it's hard to say that, but I do think on how I'm working now, I kind of let the work- life overtake almost my personal life with COVID because I was never leaving the house. And it's like, okay, well I'm here, so yeah, I can jump on a Zoom. It's not like I'm in my car commuting. It's not like I'm doing something else. And so, before I went on leave, I was working a lot, and now, I'm just not willing to put that much time, right? And I don't have that much time. Otherwise it's like, why do I have a child? And so I'm finding that I definitely am having to pick up much more ruthless prioritization, and then also prioritizing the things that I need, the time I need to move forward on the agenda that impacts what I have to do, prioritizing that. Because historically in my whole life, I've prioritized everyone else over myself. And so it's been a big exercise of identifying, okay, if I'm on the board for these metrics for this month, am I prioritizing the meetings that are going to get us to those metrics versus helping Dena to get to her metrics or whatever.

Dena Upton: Yeah, yeah. Yeah, yeah. Yeah. You mentioned to me that you found inspiration in some of the children's books that you've been reading to Liliana. Can you share an example of how you're bringing that into your day- to- day?

Tricia Gellman: Yeah. It's funny because you think of children's books as just these fluffy little nursery rhymes and things that, but in today's-

Dena Upton: Lots of good nuggets in there.

Tricia Gellman: Yeah, there's so many nuggets. There's one book that's about this fish and how it has all these shiny scales, and it thinks it's the coolest fish in the sea. And there's a little meager fish that wants one of his shiny scales, and he's like," No way, I'm not going to give it to you." And it's just so rude. And so I'm like, | Liliana, that fish is being rude. You don't want to be rude." It doesn't say that in the book, but that's the lesson. And then in the end, it gives away its scales so then it can kind of have a posse of people to hang out with and not be so lonely. And I think that's a really good work lesson, right? How do you, as a leader, bring everybody along, versus just trying to chart your own path yourself and be all ego- driven and everything else? There's another book, which is a Jamie Lee Curtis book about Big Words for Little People or something. And it has words like impossible and confidence and perseverance. And it's interesting, when we were talking about perseverance and I was like," Well, you're here because we had a lot of perseverance." And it just makes you realize the things that matter again, back to that whole point of what matters. And I think that that's one of my big lessons is about the journey. I think that's something that defines me. When I was a lot younger and I started doing Ironman, our coach was basically talking about how life is more about the journey than it is about the destination. And that sounds weird because you're like," Oh, you're going to do this race and it's a total destination to get the race checkbox," but you don't really enjoy it if you just focus on getting to the race. You have to enjoy the journey along the way. And a lot of times, things don't work out the way you want. So you have to have the perseverance or at least understand truly what matters to you and what's on your checkbox list at any given time.

Dena Upton: You're the CMO at a hyper- growth software company. You're also the mom of a four month right now. So time is not necessarily on your side. How do you manage that, Tricia? I know you've been back at work for a little over a month. You talked a bit about sort of delegating to your teams, but any tricks that you have or thought process of philosophy you have on trying to be really good at both of those things, mom, spouse, all three of those things, mom, spouse, CMO?

Tricia Gellman: Yeah, yeah. I mean, I think there's just so many things and I think that's something about, as you go through life, you go from being a single person and being super selfish, to kind of expanding your horizon in terms of what it is that you're trying to juggle. And I think for me right now, for sure once you have a child, it's like where do you find time for yourself and how do you make sure that you do have some of your self time? Because otherwise, if you're not having strength yourself, then you basically can't give to everybody else, whether it's your work or your family or your child or whatever. So generally what I'm trying to do is a couple of days a week get up really early, like 5: 30 or 6: 00, and then I am trying to work out for 30 minutes. And then instead of being the person who's feeding Liliana before the nanny comes, I've agreed with my husband that he does that so I can get ready. And I think that's really... I mean, even at home, how are you delegating what needs to get done? And then during the day, I'm really prioritizing what it is I'm doing, what meetings am I spending time in, where am I giving my time. Because I do really pride myself on trying to mentor people and make time for people that I just meet through LinkedIn and listeners here who reach out and say," Hey, I'd love to get your opinion on this or that." And so really thinking twice of what am I doing with my time, why am I doing it, what bucket does it fill? And then with my direct reports, I have a Google Doc that I go through for every one- on- one so that we take the notes and it's really clear what are we working on. And that's a good reference. So you're juggling so many different things, you can always go back to it. You don't forget something. I think that's really good too.

Dena Upton: Yeah. And one of the things, I think we talked a little bit about this earlier, but when you were interviewing Drift for this role, you had told me that relationships were really important. So you were interviewing the executive team, how we interacted with each other, how we supported each other. How did you know Drift was the spot for you?

Tricia Gellman: Yeah, I think, as a CMO, I think this is one of the hardest things, to be honest. Because there's a lot of open positions for VP of marketing or CMO depending on the size of the company, but there's a whole multi- faceted thing I think that has to work. You have to find a technology that you're passionate about. Because it's a lot of work to be a CMO, and if you're not passionate about what the product is, you're up shits creek. The next thing is the team. Do you want to work with these people and do you feel they are going to be your peers? Are you going to learn from them? Are they really going to help to accomplish the goals? Because you don't want to be in the situation where you're the only one who is kind of on this page of whatever the goals might be. And then finally, it's like, are you going to have the right tools and materials to kind of be successful? I interviewed at companies where they didn't have values that made sense. And so there were no women in the executive team, there was no women in the board. There was no concept of a HR or people person who was helping to push forward on culture. And I'm like, well, I'm going to fail because you want me to build a high performing marketing team, but you don't care about the things that people I would want to hire care about. And so then I'm not going to be able to build that team. And so I think that to me was the interview process, is to try and figure out all of these things. And I think in the end of the day, one, I love the fact that DC and Elias worked together before, because it's also a dance to get the executive team together and to have them gel. And so at least if you have part of the team that's worked together before and they've been successful together before, you know that some of that at least is in the check boxes. So to me, that was great. And then also seeing other people that I thought I would love to work with and that had a constant desire to learn and grow, I love that about Drift.

Dena Upton: Awesome.

Tricia Gellman: Well, Dena, we're running out of time, and I thought it would be pretty scary to talk about myself, but I think it's great. And one of the things that I always do in the end of my show is I ask the person, the guest to share one piece of advice. And so I think I have to close on one piece of advice. And I think we've talked about it a lot, but my piece of advice is really to check on yourself and identify what are your priorities. Not what do you want to do, what title do you want to have, but really what are the priorities and the things that matter to you? Is it about bringing your whole self to work? Is it about working in the most innovative technology? What are those things? And then how do you start to carve out your career path to achieve your career goals, but at the same time, make sure that you're not sacrificing on those things that really matter to you.

Dena Upton: Love it.

Tricia Gellman: So that's a wrap. And I want to thank you all for listening to CMO Conversations where I am the host and also today the guest. Thank you, Dena, for having this conversation with me. I always love our conversations. And you're a mom as well, and you always bring great news about your children and your family to work, which I think it just lightens the load and helps make everything fun. So thank you for that.

Dena Upton: Thank you.

Tricia Gellman: You can help us promote the show by going into whatever channel you use to download your podcasts and giving us five thumbs, six stars, whatever it might be, and spread the word. Thank you for listening. Maybe you're happy to hear that in my next episode, I will be interviewing an actual CMO, not myself. So thanks for being a listener.


Tricia Gellman is the host of CMO Conversations, and on this episode, she’s also the guest. At the end of 2020, Tricia went on maternity leave to welcome her daughter into the world. But now she’s back at it and figuring out the balance of being a new mom, wife, and – you guessed it – CMO. She’s joined by Dena Upton, Drift’s Chief People Officer, for a candid discussion about her journey to motherhood, her transition back to work, and what she’s learned so far.

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends. You can connect with Tricia and Vidya on Twitter @triciagellman @heydenaupton @DriftPodcasts


Tricia's Article in Business Insider --> I'm a 3-time CMO and 5-time ironman triathlete, but having a child is the hardest thing I've ever done:  https://www.businessinsider.com/drift-cmo-tricia-gellman-motherhood-infertility-ivf-loss-career-2020-10

The Rainbow Fish by Marcus Pfister https://bookshop.org/books/the-rainbow-fish/9781558585362

Big Words for Little People by Jamie Lee Curtis https://bookshop.org/books/big-words-for-little-people/9780061127595