Greg Stuart: This is Building Better CMOs. Let’s get back to my conversation with Heather Freeland, the chief brand officer at Adobe.

Knowing what you know now and what you see, would you wish you'd modified your education in some regard, or maybe even modified your experience? I'm trying to understand what is the precursor now to becoming the CMO and managing all these trains moving around. I don't know what that job is.

Heather Freeland: It's super interesting. So when I left Facebook, I actually initially took the job as VP of strategy and operations at Lyft, and ultimately was promoted to run all of marketing. And I did it because I specifically knew I needed to fine-tune that skill set. I knew I had done a lot of the work and a lot of the learning at Facebook, but I was like, "Now is the time to put it to the test at a company that is quickly scaling."

And so for me, that's how I've kind of managed my whole career, actually, is I'm going around gathering different skills in each role I have taken. So like, at MTV Networks, I took a role building out their vertical ad networks when that was a big thing back in 2008 and building out ad technology because I knew I needed to know more about media. I knew I needed to learn more about sales. I was working with the sales organization.

And so same when I went to Lyft, I wanted to really fine-tune those operational skills. And not surprisingly, the operational challenges I saw there were not dissimilar to those I saw at Facebook, were not dissimilar to those I see at Adobe. It is often an afterthought. But when I was at Lyft, I reported into one of our co-founders, John Zimmer, and by the end of my time there, he said, "I've come to see that whenever I will hire another marketing leader, I need to test for operational skills and savvy."

GS: Oh, wow. He figured that out.

HF: Yeah.

GS: Interesting. Boy, this is a whole other thing. I got to tell you, I think I see a whole new MMA agenda item here, a new think tank for us. I don't know really what it is or what it looks like.

HF: Well, I'm happy to help figure that out.

GS: And listen, this is important to Adobe being able to provide success. So, I mean, it totally would make sense at the industry level that the MMA work on a problem like this. Listen, I love what you just said, and I think so many people don't get that. There's a lot of paths up the mountain. Okay?

HF: Yep.

GS: And I guarantee you can't see looking forward what is the best one. You really can't. Just no way. It's only in reflection and looking back that you see how you got to where you did. It's funny. I have two daughters, just graduated from college, and the one just started her first day of work at NBCU today. Very proud of her.

HF: Ah, that's exciting.

GS: Isn't that exciting? Yeah.

HF: Amazing.

GS: So here's the question I have for you, though, around this. What experiences might you tell somebody to look to go after for this? There's two ways you can answer that question. What experiences would you suggest that somebody try to get? Or what are the new capabilities that you're starting to hire for? Is there anything you've changed in your hiring patterns? Have you brought in new roles that maybe you didn't have 10, 15, god forbid, 20 years ago? Talk a little bit about those.

HF: Yeah.

GS: They're both different angles at the same problem.

HF: So it's interesting, and I touched on this a little bit before, on how I kind of approached my career by gathering different skill sets. And every job I took, I had almost my learning agenda in mind for that role so that I could kind of go deep in a certain area, whether that was ad tech or sales or creative or what have you. And so I think that has served me well in terms of having a very well-rounded marketing background and perspective because it is so multifaceted these days. We have to wear so many different hats as marketing leaders.

But I think one phrase that always captures it well for me is that when I was at Facebook, they talked about it not being a career ladder but a career jungle gym. You remember those god awful dodecahedron jungle gyms from when you were little, and there was no straight path. You had to crawl all around to get to the top.

GS: I didn't need you to even try to visualize that. I saw it right away. I totally, yep, got it.

HF: You have to take different turns, and that will not just help you gain skills across the board but will also help you figure out what you're good at, what your passion is, what you love, and you're inherently going to be better at something you love and get excited about, too. So it's important to find that, particularly if you're more junior in your career. So for me, that was a big part of it.

Now, to your other half of your question, in terms of what I look for when I'm hiring someone. I think that the key things I look for—and it depends on the role, I actually interviewed a candidate this morning—and two questions are pretty common no matter what role I'm interviewing for. And one is ability to kind of influence and partner cross-functionally. And I think for marketers, that is absolutely critical because we are such an inherently cross-functional organization. We have to navigate with IT, with product, with finance, and within marketing, and you need to know how to influence.

GS: We are no longer managing a function. We are managing a coalition.

HF: Yes, that is spot on. Spot on. And so that is one. And then the other is the ability to turn an idea to action, which is operations. How do you make things happen and get them out the door smoothly and easily? And so I do think those are... Literally I kind of have questions I ask in those territories because I think it's critical for people to know how to execute and get things done in an efficient way.

And then I often ask as a follow on to that, "How do you optimize that? How do you constantly improve that and adapt that?" Because you need to have flexibility because things are changing so fast right now in our worlds.

GS: I think we could do a whole session on just that one topic right there and all the attributes to it.

So did you set out to be a CMO? Was that the goal? Did you just kind of stumble upon it? And what did you do? So given that also—back to your jungle gym metaphor, not a career ladder but a jungle gym—talk a little bit about how you got there.

HF: Yeah, I mean, I absolutely kind of set my eyes on that goal earlier on in my career, and that was why I approached it the way that I did in terms of collecting the skills that I knew I would need in that capacity. It's also why, even when I went to business school, I actually did not concentrate in marketing. I concentrated in management and diversified my classes in accounting, in finance, in operations, in leadership because I knew that a lot of the marketing stuff I would learn on the job.

It was more about knowing and understanding how to work within an organization and how to talk the talk of all the other functions, that coalition, as you mentioned. So I think for me, it was kind of the pivot I made to business school, and then going to Digitas and getting exposure to incredible brands. I had the opportunity to work with Nike and American Express and Converse. So it was just a best-in-class training model in working with a great brand. And it was also at the forefront for both American Express and Nike in thinking about digital transformation, so that was an incredible time to be there.

And then going from there to MTV Networks to diversify my understanding of how to work with a sales organization, which is critical as a marketer to understand that dynamic, to really dig in deep on media, media sales, and even ad tech. But the reason I actually took that job was because I had this vision of, if you're a good CMO, you have to operate more like a general manager than you do a functional expert.

And so part of my role there was as a general manager of this new ad network business we were starting up, and it really widened my perspective in a new way. And then ultimately, I got offered the CMO role at Gilt City and had an opportunity to then take on brand marketing at the Gilt Groupe, which was an incredible training ground for working in a fast-moving startup. And then at Facebook had the chance to really put that all on a global stage and put that to work.

GS: Did you hesitate to go to Facebook at 2,500 people, by the way? That would've been pretty early on. In fact, you went there in 2011, so they had not made the full-on pivot to mobile at that point.

HF: No. In fact, the first product I launched was mobile ads.

GS: Oh my god.

HF: Yes. So I started, I had no time off from Gilt to Facebook because we had this product we were going to launch, and we used to joke that the only ads on Facebook would've been on your thumb because we didn't have any ads in newsfeed at the time. So they were only on the right-hand side. And so my first task at Facebook was literally launching mobile ads, and that was just an incredible time to be there and to be a part of the transformation of the industry.

GS: Incredible time. Yeah, no, listen, Carolyn Everson, who served on the board of the MMA for years and years and years, and I think one of the MMA's biggest supporters...

HF: Who was a dear partner and close partner of mine when I was there.

GS: Oh my god, had to be a totally and completely connected at the hip kind of situation, I know. But she used to talk a lot at the board about how hard it was to make that transition, that it wasn't a given at any point in time, and how hard the company... And her point was, she would say in board meetings, "If it's hard for Facebook and we are founder-led and can move, and we're a fast-moving company, what does this mean for Unilever and other companies? How hard that's going to be."

HF: I remember it incredibly clearly where Mark stood up in Hacker Square, which was the main square on campus at the time, and declared we were going to be a mobile first company. And I tell you, it was like a masterclass in change management at the company. And it happened on every level, from retraining engineers to be mobile first to new incentives and training programs and L&D and marketing and everything all along the way in terms of shifting the company. And it was amazing to have a front row seat on that.

GS: Yeah, totally, totally, totally. Listen, you've been at a number of different companies who have their own particular cultures. I mean, in fact, as I look at the list, some of them are pretty radically different cultures, I would expect.

So if you were to give advice to others who fall in your shoes, what does it mean to sort of continue to operate at the C-suite level, to be effective within those roles? What's your lessons learned?

HF: I mean, I think for me, there's probably three things, two of which may not be expected. And one, I think, is you have to be incredibly well-prepared and know your shit. I mean, honestly, the amount of prep I do for meetings and knowing the ins and outs of what's happening is a lot.

GS: Dara Treseder said the same thing on Friday. She was like all over that. She was like, "Oh my god, I am the most prepared person you will ever meet," is what she said.

HF: You have to be.

GS: Have to be, okay.

HF: And then you have to be able to clearly articulate and have a point of view. And so I think having a point of view is critical.

But the two I will say that are not often thought of but are huge, particularly in terms of leading a broader organization, a large complex organization, are kindness and gratitude. And it is not always what you would expect. But I find time and time again that I can build deep partnerships by listening, by extending help and support, by taking a meeting from someone who needs help or to bounce an idea off of me, and to be generous with my time. And I find that that has built deeper trusts and partnerships, and that enables me to get more done.

So I think that, and then the last one is gratitude because I do think none of being a good leader happens without an army of people standing there with you and making sure that they know they are appreciated, that they know their work matters, and that it is seen and that they are seen as individuals is really critical. And so I'm a big believer in practicing gratitude.

GS: So that's practicing gratitude for the team. I got that. What about your own orientation towards gratitude or where you are? How do you keep yourself pointed in the right direction? Listen, it's hard under the pressures of business sometimes to show up and be full of kindness and gratitude. I mean, I live in New York City. Those are not virtues here.

HF: No, no. I mean, I always say it starts at home. So we have a moment... I have a seven-year-old and a nine-year-old. And every night our bedtime routine—and even if I'm traveling, they call because they have to get the question in—which is, "What was your favorite part of the day?" And we spend a moment talking about what mattered to us and what we are grateful for. And having that moment to just reflect on what I'm grateful for, I have to answer the question, too. And some days it's hard. It's hard to have a good answer to that one, but it is a reminder to be appreciative of the opportunities you've been given and that you're learning every day, that you're growing every day. And I think it's really important.

There are actually studies done that the art of practicing gratitude has very real physiological benefits to your physical health as much as your mental health. So I am a huge believer in that. I did this with my team at Lyft, and I've brought this here to Adobe, too, where we have Thank You Thursdays. We start in our Slack channel, and I start posting a thank you to someone on the team. It could have been a big project they led. It could have been a little thing, they organized an event for the team, whatever it is, or I just saw them reach across the aisle to help someone on whatever it was. But the idea is that they then have to pass it on. So they then reply in the thread.

GS: Oh, so you thank somebody...

HF: I thank someone, and then they thank someone, then they thank someone, then they thank someone. And the number of emojis and GIFs that light up that Slack channel on Thursdays is heartwarming, but it just feeds this culture of gratitude across the team. And I think that's really important for all of us to be grateful for what we have and reflect on our accomplishments and what it took to get them done. It's usually not just you, it's someone else who helped you accomplish that.

GS: Well, you kind of identified it early on here. It takes larger than a village. It feels like a small metropolitan city in order to get any advertising campaign or marketing campaign done.

HF: That is for sure.

GS: And so that's a lot of gratitude to go around. Hey, let me ask you a funny question to that, too, and then we'll sort of move on here. What happens when they just don't get it right? It's hard to be grateful when they just mess it all up.

HF: Here's the thing, I think 99.9 percent of the time intentions are good. Everyone is generally well-intentioned. I do think when something goes wrong, it has to be called out. But I also think you have to do it with compassion and understanding. This is a human that you were talking to who has very real feelings. They need to understand what went wrong, but you also need to do it in a way that demonstrates, "Hey, listen, I care about you. I care about the outcome. This may have messed up, but I'm giving you this feedback because I care about you and I care about the outcome." And that's an important reorientation.

GS: Wow, I love that. I love that.

HF: Oh, yeah.

GS: Yeah, hard to do sometimes in the moment. It's funny. What I notice is that if I can take the time to find out how they got to where they did, it does, at some level, make sense. I try to remember that. At some level, if I probe, almost always, I'll go, "Oh, I see how you got there. It's not right, but I see how you got there." So we have a foundation problem here. We have an objective problem here. We have a goal problem here. We have an aiming for... usually it's aiming for the wrong thing. They thought this is the right idea. And it's like, "No, no, no. Your goal, your anchor's over here, I think, on this one." Or I find out I'm wrong.

HF: Well, and then the key is learning from it, too, and you got to learn from it. So how are we going to do this differently next time so this doesn't happen again? How are we going to instantly pivot this to improvement, not wallowing in our misery?

GS: But I love that. "Care about you and the outcome." Okay. A couple of quick rounds and we're going to wrap up and let you out of here. Okay. You ready?

HF: Great.

GS: So...

HF: Yes.

GS: Who in marketing... It can't be anybody there in Adobe, okay, or your agency, for example. Okay. Who in marketing, person or company, do you admire? Whose work do you really like? Who out there you've had a chance to interact with, you think is just phenomenal? It could be historical in your experience. Just pick on somebody or company. I'm not sure if you're watching anybody else's work right now, but...

HF: Yeah, I mean, I have to give a nod to Ann Lewnes. She's no longer at Adobe, so I can mention her.

GS: She's the greatest of all time. Totally.

HF: I know. And I joined Adobe because of her, and I had watched her career for so long and watched what she did to transform this company and build the brand. And so absolutely top of my list. I do think the person now who I love to follow is not a marketer from the beginning but has evolved into it is—and I feel like everyone must be saying this name now—is Ryan Reynolds.

And I am currently watching Welcome to Wrexham, and they have season two out. And increasingly, marketing is not about advertising but is about really authentic connections with brands. And I think that show is a masterclass and brings brands to life in meaningful ways through storytelling and where you never once feel you're being marketed about at all, yet here I am drinking Aviation gin. So I think there's just some incredible thinking, and I love that he's not a marketer and he's forcing all of us as marketers to think differently.

GS: And Ann, if I just call out to Ann Lewnes there. First off, I agree. I mean, Ryan's done an amazing job. It's incredible. The value creation he's done for himself and his shareholders is just phenomenal.

HF: Yeah.

GS: But Ann Lewnes I love. She is a graduate of the Bronx High School of Science and Technology.

HF: I know.

GS: And I love that. When I found that out, I was like, I admired her double when I heard that. Because listen, I can't imagine 30, whatever, 40, I don't know. Sorry, Ann. Years ago, being a young girl in a tech high school like that. I mean, I live in New York. Those are very hard schools to get into, and so all street cred there.

Okay, what might be most over-hyped in marketing today?

HF: This is controversial, but I'm going to say advertising.

GS: Oh, counter. Okay. Okay.

HF: Yes. Even though that is my job, I think increasingly—I mean, you touched on it before with customer experiences. But I think increasingly marketing should not be about advertising but should be about showing up authentically as a part of culture.

GS: Totally.

HF: And I talk to my team a lot about how do we become part of the cultural ether so that we are a natural part of the next generation's days, lives, the things they care about, the work they do, instead of just interrupting their experiences with advertising?

GS: You know what, Heather? I hear you on that. Yeah, exactly. I mean, I love advertising. It's what I grew up with. But you're right. Maybe...

HF: I know, me too.

GS: Maybe it's time we put it aside a little bit. Okay, well, there's another problem for me maybe to work on.

Okay. What's most underappreciated in marketing? I think I know what it's going to be. What's most underappreciated?

HF: Operations.

GS: Yeah, there we go. There was too much of a setup. So I guess, everybody, just go listen to before. If you just replay that, then you're all set.

Heather, listen, I am finding these in general to be the most fun, and I love people like you who have just a strong point of view based on the experience of what is right in the world and how we need to be better. Oh my god, I could listen to that kind of thing all day long. So I can't thank you enough for being on Building Better CMOs. Thank you.

HF: Oh, well, thank you. I've had a lot of fun, too.