Systems Thinking in Martech: How Marketers Build Antifragile Careers | Ana Mourão

00:00:00.040 — 00:01:14.940 · Jacqueline Freedman

Welcome to Making Sense of Martech. The rabbit hole goes deeper than the headlines. This is a show that pressure-tests ideas, not just platforms. On the Hot Seat today, we have Ana Mourão. Her new book argues that marketers who lead martech projects and think in systems build careers that get stronger with every disruption.

In the Netflix show The Queen's Gambit, Beth Harmon is a chess prodigy who sees the whole board. It makes her unbeatable. It also leaves her alone at the table. Today we're going to pressure-test that trade: what it costs to see the whole board and which small losses are actually worth it. Don't forget to subscribe to the podcast and our newsletter.

A little bit about Ana first. She is a brand-side Global CRM Manager and a customer data advisor, and a close personal friend. She has spent 15+ years in martech at Fortune 500 companies, including 3M, Charles Schwab, and Starwood Hotels. Her new book is Strategic Marketing Skills: How to Build Technology-Driven Expertise That Delivers Business Value.

Full disclosure: I am quoted in it. However, that does not make things easier for her or me, for that matter. Welcome, Ana. Thank you so much for being here.

00:01:15.140 — 00:01:16.700 · Ana Mourão

Thank you so much for having me.

00:01:16.740 — 00:01:34.700 · Jacqueline Freedman

That makes me so happy. And also, Ana was like the first encourager of me starting to write essays, and so I am super grateful—just fans of each other. So before we dive in, we're going to start the episode like we always do with some rapid fire. First and foremost, what was your first martech tool?

00:01:34.740 — 00:01:41.260 · Ana Mourão

I'm going to sound like a fossil here, but it was WebTrends.

00:01:43.220 — 00:01:44.900 · Jacqueline Freedman

That is a throwback.

00:01:44.980 — 00:01:50.260 · Ana Mourão

Yeah, it's in the Jurassic time. I love martech. I was using WebTrends.

00:01:50.260 — 00:01:59.440 · Jacqueline Freedman

So nice. Okay, this is related to our episode that we'll get into. But has a boss ever called you "difficult" instead of "strategic"?

00:01:59.440 — 00:02:38.000 · Ana Mourão

I think that for the most part, when I have had those types of issues with any boss—and I'm talking years, many years ago, before where I am now—I would say that it was mostly because I had a very hard time explaining myself, and I work with things that are kind of technical, right, in the intersection of marketing and technology.

So I think that it wasn't that I was considered difficult, but it was like, okay, you know, "she's technical and I'm not really understanding what she means or what benefit that would bring." I think that was more the miscommunication that I have had in the past.

00:02:38.200 — 00:02:56.560 · Jacqueline Freedman

That makes sense. And that translation is, I think, really the hardest part of our industry: being able to speak to every different audience and meet them where they are. It's hard to do. It takes practice. Okay, and in one line, what will your book have gotten wrong a year from now?

00:02:56.640 — 00:03:35.930 · Ana Mourão

I tried to write a very evergreen book, right? So hopefully where it gets wrong a year from now is that a lot of what I advise concerning how do you communicate with the other teams and how you make sure that marketers are leading martech projects—are not needed anymore because marketers are already leading the martech projects, right?

And everything is going as it should be. All the teams working together around business objectives, right? So I hope that my book can make itself—I hope that my book makes itself obsolete at the end, because it will mean that marketers are really leading those conversations.

00:03:35.930 — 00:03:44.050 · Jacqueline Freedman

I love that goal. It's kind of the goal of always trying to automate yourself out of a job, and that is the goal.

00:03:44.090 — 00:03:48.610 · Ana Mourão

Exactly. If you improve [through] continuous improvement through test and iteration, okay.

00:03:48.610 — 00:03:53.010 · Jacqueline Freedman

What do you consider the most overrated metric on a marketing dashboard?

00:03:53.050 — 00:04:13.870 · Ana Mourão

I would say ROAS—return on ad spend—especially because sometimes we take into consideration media, but we may not take into consideration the costs around creative, right, or the time of people involved. So I think it's always tricky. It's a tricky metric as well.

00:04:13.910 — 00:04:19.549 · Jacqueline Freedman

Systems thinking or analysis paralysis: which do you most commonly see?

00:04:19.630 — 00:04:54.070 · Ana Mourão

Unfortunately, analysis paralysis. Sometimes we are in situations where we see just one piece of the puzzle or few pieces of the puzzle, and then we're like, okay, so what should I do? And you get stuck on how do you start or how you proceed? And when you see more of the system—the entire system that enables you to say, okay, I think I can see the levers that I can push here or I can understand them—what these changes may represent in the future, right?

As we go through the whole system and the whole processes, for instance.

00:04:54.110 — 00:04:58.370 · Jacqueline Freedman

Makes sense. All right, last but not least, what is your hottest take?

00:04:58.370 — 00:06:29.950 · Ana Mourão

So actually I have two. One is what I mentioned already: that marketers should lead martech projects and martech conversations, right? MarTech stands for Marketing Technology. And if it's marketing technology, marketers must be highly involved and they should lead some of those conversations. And I think a lot of marketers actually miss this opportunity because they may think that, you know, "oh, no, IT will set it up for me. Other teams, ops will take care." But actually, the knowledge of the marketer is needed as well, right? That use case, that context. So that's one.

And then the second, which is related to the first, is that by going through that process, by leading those marketing technology projects, marketers can actually make their own careers antifragile. And I use here the antifragile term that I borrowed from Nassim Taleb's Black Swan theory, because it's not only about making the career more resilient. It's actually making sure that your career, your marketing career, gets better after each disruption and does not depend on one specific technology, right?

So I think the two things go together. And but during my writing of the book and researching of my book, I ended up realizing this, right? If you go through these processes to make the most out of technology, marketing technology, for your company, you are already making your career more resilient and more antifragile.

00:06:29.990 — 00:07:01.930 · Jacqueline Freedman

I couldn't agree more. To set the stage, you have made a career out of seeing the whole board—really systems thinking—while everyone around you is likely defending just a single tiny bit of the situation. Now you've put that view in a book. Now let's pressure-test this together. Your book leans on Donella Meadows: "change the relationships between components, not the components." What does that look like inside a CDP program? And not just on a very pretty slide?

00:07:02.170 — 00:08:52.080 · Ana Mourão

This means that you are going to make the most with what you have, right? So it's not like, "oh no, I'm going to wait until we have the new technology or I'm only capable of doing such and such with this platform." Well, perhaps you won't be able to use the platform that you want or that you prefer, right?

And you have to work with what you have. That's the very high-level idea: you're making the most out of what you have, right? So in the case of a CDP project or any other type of large marketing project, it's really about understanding how that technology, that platform, can help you—not only with all the activities that are customer-facing, right, everything that generates more conversion, engagement, etc.—but also how can they help your own operations, right? How can they help—maybe your campaigns go to market faster? They can help you be more iterative and launch campaigns faster, or be able to share those insights that you learn in a better way with the other teams that are involved, and create a feedback loop that helps everyone, right?

So how is it that those platforms can help you on both ends? Because they can. And I think sometimes marketers over-index, right, on everything that is customer-facing, which is of course awesome. It's what we need to do. But they need the opportunity, right, to improve processes or decrease time to market or decrease dependencies on external vendors while they're also going through those platforms or developing the processes around it, the governance around it.

So I think that's what I mean by that. And that's what I address in the book: how is it that you take advantage of all those opportunities, whichever way they present themselves, right? That's the idea.

00:08:52.080 — 00:09:02.480 · Jacqueline Freedman

It's making perfect the enemy of good, and that is not helpful in these situations. What was the first component and relationship you changed, and what did it cost?

00:09:02.520 — 00:10:11.620 · Ana Mourão

I think that the cost was really making sure that the governance was in place. So it was about making sure that whenever we had this stack that had to collect data, unify data, and then make the data ready for activation. So what I had to do—what I helped do—was really make sure that there were processes around it.

And those processes helped the business stakeholders, like the marketers, also be accountable for the quality of the data entering the stack, because if the data comes as clean as possible, it's going to be ingested, digested, and unified much faster and be ready for the activation that the business stakeholder wants to do way faster.

So it was that realization that business stakeholders could also be the co-owners of the data quality. And that was really, really helpful. And it's something that helped us really make sure that we had our governance in place, and that governance is very portable as well, right? Depending [on what changes], we can change the components, but the governance stays.

So that's the beauty.

00:10:11.660 — 00:10:23.420 · Jacqueline Freedman

It's kind of like total cost of ownership but in a different perspective. Yes, and it's not something that's typically considered when you're crunching the numbers to calculate something to determine if it's the right approach. We don't think about that.

00:10:23.460 — 00:10:24.100 · Ana Mourão

Exactly.

00:10:24.100 — 00:10:37.420 · Jacqueline Freedman

So for you, where's the line between systems thinking and never shipping anything, because we're just too pie-in-the-sky? We know how it will disrupt what exists or what we seek and aspire to.

00:10:37.460 — 00:11:15.360 · Ana Mourão

So systems thinking should really be put in place to support the business objectives. You have to make sure that the system would deliver against that. If the system that you were thinking of or designing or implementing does not deliver against those two pillars—so to speak—business objectives, then yes, it's not worth it.

It's going to be pie in the sky. So it needs to be very practical. Even though it's something that seems more subjective at the end, it needs to be very practical. It needs to match against the business objectives that you have.

00:11:15.400 — 00:11:20.920 · Jacqueline Freedman

Love that pragmatism. So how would you tell your boss the difference if they're inquiring?

00:11:20.920 — 00:12:28.660 · Ana Mourão

So I would tell my boss what systems thinking would bring. If we go that way—if we think of all those components together as a system, instead of just thinking them on their own—we can ship faster the next campaign, for instance, or we can make sure that we can implement more tests and with that get more insights to create a feedback loop.

Or we can be faster in creating content and test it to understand what engages our client the most. And then from there, we can develop a new plan and make sure that we use what performed best, right? So all those things—I think that sometimes our bosses, people that are not on the day-to-day, they may not see. So it's really up to us to make them see and then get their feedback, because once they can picture that, they're like, "okay, I understand."

So this is what I think, and this is where I think we could make the most impact. And then it becomes really a collaboration. And it's not just you thinking by yourself. It's something that's you, your boss, the team, etc., and it's much more engaging, much more fun.

00:12:28.700 — 00:12:31.060 · Jacqueline Freedman

Yeah, it's a shared language and perspective.

00:12:31.100 — 00:12:31.820 · Ana Mourão

Exactly.

00:12:31.820 — 00:13:12.720 · Jacqueline Freedman

And so in my opinion, seeing all of this is the easiest part—and it's not an easy thing to do—but saying it out loud is where things can get really difficult and expensive as well. In terms of our industry, I want to dive into maybe something unpopular about it.

Your book calls integration the most in-demand capability in marketing. If that is true, you would expect integrators to be rather protected. So let's find out whether they are. Who resists? And what are they trying to protect? Is it silos? Vendor sprawl? Visible busywork? When you integrate, at the end, you are going to change the way someone works.

00:13:19.440 — 00:13:21.920 · Jacqueline Freedman

Something will change, and change is hard.

00:13:21.960 — 00:13:50.460 · Ana Mourão

Exactly. Usually, human beings are resistant to change because it's going to change your day-to-day, the way you are used to working. Top-down like, "oh, I came and communicated innovation. Go do it." No, it's something like, "okay, if we see things this way, what are the benefits, right?" So can we start with something small? Can we start with a small test, right? It may be that you cannot go and do the same thing during all the martech activities at once. No, that's okay. You can start.

00:13:50.500 — 00:13:52.020 · Jacqueline Freedman

It would be so much more fun.

00:13:52.940 — 00:14:24.980 · Ana Mourão

But sometimes you have to go and get a small piece and say, "okay, I'm going to get this small piece. Let's think holistically. Let's think as a system, and let's see how that could benefit our customers and our processes." And then we can test there. "Did it work? Yes. Okay, so now we can do something bigger, or we can go and see the review of the entire stack through all those lenses."

It's going to be a lot of give and take for the integrator to be able to integrate. Really, in my opinion and in my experience.

00:14:24.980 — 00:14:56.710 · Jacqueline Freedman

It's so interesting. We're so in demand and yet we get the most resistance when we actually do the work. Yes. And it's really the job: connecting things, integrating things—the technicality. But it's actually really the change management and the interpersonal management more than any other component of any business. It is uniquely difficult in that regard.

00:14:56.750 — 00:15:25.070 · Ana Mourão

Yes, absolutely. It's way more difficult than the technology itself or even the architecture. We think that the architecture is going to be like, "oh no, I have to put the pieces here and the components in this way." But the hardest part—that's the part that's the easiest part. The hardest part is the change management: making sure that the processes serve the stack and vice versa, right? That everything is on like a virtuous cycle loop. So that's really the hardest part for sure.

00:15:25.150 — 00:15:54.050 · Jacqueline Freedman

I agree. In the phrase "people, process, and tools," it's almost always the people. It's the hardest part. We humans are complex and difficult and not by nature systems thinkers, at least not in our current modern era. So for the folks who are successful in these roles, how are they protected? How are they not seen as negative Nancies or naysayers of, "oh, this isn't going to work well"?

00:15:54.410 — 00:17:58.210 · Ana Mourão

Well, I hope they're protected, right? There are no guarantees, unfortunately. But what I would say is what helps them is that they show the benefits. So they're the ones who come, suggest the changes, help implement the changes, and then bring the learnings and then iterate upon it. I think that these people—they do this whole process, and then they come with the insights and they already suggest a new hypothesis to test.

So they created that virtuous cycle, and they run it. And this is what I think a lot of companies realize, and they cannot name it properly. Maybe it's not something that's like, "oh, it's on my review," or no. But being able to put those little or even big virtuous cycles in place where the technology, the people, and the processes, they're all feeding off each other and it's compounding—because you're getting more insights.

Those insights come back as a feedback loop, and you're enriching the data and the processes are better. And this allows the company to make better creative that engages more, for instance, right? So when that becomes clear, then it's like, "wow, wow." Because that is something that again compounds. It lives beyond the person even. It goes beyond the company sometimes, through relationships with vendors, different types of vendors. So that's the beauty, right?

The beauty is [to] go through the entire process. And that's hard because sometimes we start with the product, then we don't see the results, and then we give up. We're not able to communicate the results well. And then things kind of die off. And there is no iteration. There is no like next steps. So you have to go through this even when it's hard and you're not seeing it. Let's try to make it in a way where if you're not seeing yet the results on the customer-facing stuff, you're already seeing some results on the operational side, vice versa, right? So that you always have something that you can work with and continue and be iterating, etc.

00:17:58.450 — 00:18:25.770 · Jacqueline Freedman

Agreed. It's almost like a daily practice. Be solution-oriented. Yes, address the problems, but you can't harp on them too much. And instead, like, "we've got the solution. We have to just rally and make it possible." It's always finding the silver lining of a mistake, an issue, a problem.

And I hate it because it shouldn't be our job, but it's like we have to market to everyone.

00:18:25.810 — 00:18:26.490 · Ana Mourão

Exactly.

00:18:26.490 — 00:18:58.750 · Jacqueline Freedman

And additionally, I think the folks who struggle probably the most with this—outside of maybe politics, bureaucracy, you know, the things that get baked in—is those who've never been marketers before as well. Because if you've only ever been a technologist or systems integrator and you don't understand everyone that you are, you know, you're the nexus point in the center of that universe. If you don't understand everyone that you're serving, how are you supposed to get everyone on the same page? I don't know.

00:18:58.790 — 00:19:15.070 · Ana Mourão

Exactly. So yes. So I think this is the opportunity for those marketers who live in the intersection of marketing technology: be that person, be the one doing this, be the one communicating and going after this and carrying that torch, so to speak.

00:19:15.110 — 00:19:36.410 · Jacqueline Freedman

That's the opportunity. Speaking of kind of quelling fears around change management: Have you ever accidentally intimidated a boss by accident? What did they do? How did they respond? Because that's one of the downfalls of being a systems thinker. You think big picture, and I can be a threat.

00:19:36.450 — 00:20:34.300 · Ana Mourão

I would say that throughout my career, before what I'm doing now—where I am now—at this point, I don't think that I intimidated [anyone]. I think the change itself is intimidating. So sometimes I would say things like, "okay, let's do this and break the silence." And it's like, "whoa." They would say, "well, you know, I see it, but the intention is good, but I'm concerned how we go about it," right?

So I think that change management part of it is what is really concerning and scary. And sometimes you're the one delivering it, right? So hopefully I didn't take that personally. And I was like, "no, I understand because change management is hard. So that's how we can do it."

But not all companies [can do it]. Sometimes you can do it right. In some companies they won't be able to do it at that point, to do the whole systems thinking. It's going to be one piece, or so. You have to also understand the environment you're in, in that sense.

00:20:34.340 — 00:21:42.880 · Jacqueline Freedman

Well, especially if you're thinking such a big picture. Like, it is kind of overwhelming. It is. If you're just being informed of all of these issues—it's not one small fire drill, except it is. It can be taken in a larger context. I think I've intimidated a few bosses unintentionally. It's not like I'm ever trying to intimidate anyone or anything.

I just get told that I'm that. And I did have one boss early in my career. I will always respect the ownership of it. Not that we need to be friends, but the person made my life a living hell for six weeks. This person had to approve that change in the transition meeting. This person owned that. They were intimidated by me and gave me hell.

And it was the first time when I was like, "oh, okay, we can like truly apologize for our behavior, and I deeply respect the person." Don't need to be friends, but I respect that they owned and acknowledged their own stuff because it wasn't me.

00:21:42.920 — 00:21:43.640 · Ana Mourão

Yes.

00:21:43.720 — 00:21:45.160 · Jacqueline Freedman

That's very much true.

00:21:45.200 — 00:21:46.480 · Ana Mourão

Yes, that's very much true.

00:21:46.480 — 00:21:46.720 · Jacqueline Freedman

And.

00:21:46.760 — 00:21:49.760 · Ana Mourão

That's very mature of the person, I would say.

00:21:49.800 — 00:22:09.960 · Jacqueline Freedman

I think a lot of people in our industry, specifically, especially if we're broad thinkers, we can get labeled as trying to do something when it's actually not. There shouldn't be ego in that. And we all have our own ego, and sometimes our egos get in the way of progress for sure.

00:22:10.000 — 00:22:55.020 · Ana Mourão

And in those cases, what I would say also is also have this long-term view of your career. So if in a place you are not able to do it because of a boss or what have you, you still tried. You still put in the work. You did your part. Even if that doesn't bear fruit there, you are where you are right now.

You are making that happen for you, for your career. So don't be discouraged. Even if you cannot apply it right away, you will be able to. So put in the work. Try [to] get yourself out there on the systems thinking, on having that systemic view of marketing, because that is going to benefit you in the medium and long term for sure.

So keep [going].

00:22:55.020 — 00:23:20.980 · Jacqueline Freedman

It's also a signal of how it's being received—either by your delivery or is it a reflection of the individual you're delivering it to? Or thirdly, is it a reflection of what the company's philosophy is and if it's a fit or not? And not every company is a fit. And if you are in the place and have the privilege of maybe looking elsewhere while I have a job, [you want to] be more receptive.

00:23:21.060 — 00:23:22.420 · Ana Mourão

Be more receptive.

00:23:22.460 — 00:23:36.880 · Jacqueline Freedman

You want to be in a place where your thoughts and ideas are received in a manner in which it is not taken as a personal attack, but as a solution to an institutional issue. And it can be big. It can be small.

00:23:36.880 — 00:23:37.600 · Ana Mourão

Exactly.

00:23:37.600 — 00:23:48.120 · Jacqueline Freedman

But you want to be somewhere where you're valued. And hopefully we all are in a place where that will happen because we're forever needed, whether they're willing to admit it or not.

00:23:48.160 — 00:23:49.040 · Ana Mourão

Absolutely.

00:23:49.080 — 00:24:34.580 · Jacqueline Freedman

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And now back to the episode. The next question is whether your career survives the next disruption moment—either it's a complete system change or you recognize something more needs to be addressed. And so it's kind of a complex gambit you're put into. And I think there's a lot of help with the framework you've built.

And your framework is really on experimentation and small bets, capped downside—something learned either way—and having folks aligned along for the ride. To your point, some people will call that antifragility. Fair. And I want you to say it your way. But it makes me think: in chess, the Queen's Gambit gives up a pawn early to take the center.

Obviously, great TV show, but it just reminds me of that same idea: a small, deliberate loss for a better long-term position. Is a small bet with capped downside your version of antifragility? Or if you had to encapsulate how you approach things?

00:26:27.580 — 00:27:59.070 · Ana Mourão

Well, the Queen's Gambit analogy—thank you so much. I would say that having those small gambits, right—it's actually putting in the work to become antifragile: developing the hypothesis, testing the hypothesis, bringing that back to the appropriate teams, sharing those insights, right. That is the work.

And if you do that over and over again, you are really, really, really putting in the work to think as a systems thinker regardless of the technology. Again, the technology may change, but you will still be able to develop your own hypothesis and help with any practice and bring back the insights and learn.

So I would say that that's the foundation for antifragility. But antifragility will be a way of developing our career thinking in two ways, right? What helps me right now on my day-to-day and what helps me in the future, what helps me throughout my career: the big-picture thinking.

Automation is coming. AI is taking a lot of that operational [work], so you don't want to be cornering that position, right? But on the other hand, you also don't want to be the pie-in-the-sky that we're just thinking holistically but it doesn't apply on the day-to-day. So you have to be mixing both. So by mixing both and having these small bets, I think that's how you make the career antifragile.

00:27:59.110 — 00:29:15.610 · Jacqueline Freedman

You have someone more senior than you who maybe isn't as experienced in our space. The easiest example is, "I want to have this email sent as a fully designed, image-based, want to look perfect and exactly like what our designer wants," and then doing a 50/50 test with the exact same content, just either completely simple plain text or just pared down.

So the experiment is literally, "okay, let's see what the numbers pull"—where, who wins? And so my favorite thing is disproving people with exact data and knowing you might have to be a little upset that you're wasting, quote-unquote, a campaign on something you know won't deliver. But it also builds credibility: "see, I can meet you halfway, but also we're going to learn about our audience."

And then we have this historical reporting of, "yeah, it doesn't work for our audience. How about we try this?" and then you iterate on, "okay, now let's try plain text versus just a pared-down, you know, hero image." I don't need to win this, but I will win something.

00:29:15.770 — 00:30:26.450 · Ana Mourão

And plus, it makes it long personal. The customers are telling us what they prefer. Sometimes your hypothesis will be tested. Sometimes your hypothesis will be disproven. Yay! And now I know that it doesn't work, right? So it's having that mindframe, that attitude, right? That also helps because we're like, "okay, it's not personal.

Let's put it out there. Whatever wins wins. And we learn, right?" So you go back to the person that had the idea of the holy meal as an image, and said, "you know what, we tested it and the customer told us otherwise. So great. Now we know," so that they feel encouraged to come with those ideas again, because you also don't want people to