Ashley Simon on Connecting the Dots Between Ideas and People
Mixing Board Studio Session
Ashley is a senior marketing executive with over 15 years of leading brand and product GTM strategies for Medium, Airbnb, Foursquare, MTV, Upworthy, Daily Harvest, and more. She’s a creative, scrappy, and hands-on leader with expertise in brand strategy, leading visual content creation, acquiring and retaining customers, and establishing growth partnerships. She also has an entrepreneurial spirit — she co-founded Curious Elixirs, co-authored the satirical book Where Does Your Penis Belong?, and launched the My Body Does campaign covered in Mic, People, and MTV News. She’s a certified yoga instructor, too.
In this Studio Session, Ashley and Mixing Board Founder Sean Garrett talk about why it’s essential to question your own assumptions, how good marketing is simply staying centered on customers, feeling good about failure, and the often existential and ‘blobby’ nature of doing brand and comms work today.
SG: First steps always fascinate me. You lived in Cape Town after school. Why South Africa? And how did it impact you?
AS: I was a gender studies major in college and I wrote my thesis on domestic violence in South Africa. I was specifically focused on why it was that South Africa had some of the most progressive legislation in the world, in terms of prosecuting gender-based violence and supporting women through the judicial process, and yet their rates of gender-based violence were doing nothing but increasing. Women weren’t taking advantage of all of these resources and new laws. I focused on the disconnect there.
In 2003, I lived in Cape Town for about nine months. I was studying with a couple professors at the University of Cape Town, doing field research, and trying to make friends (mostly unsuccessfully) in a new culture where everyone was just like, “Why are you here?” But it was a really great experience. One of my biggest learnings was — whatever you think you know, you’re probably wrong. Or maybe half right. I had spent so much time studying, doing all this prep work, sitting with all these professors. Then I got out into the field where I was interviewing real women, who were in really serious abusive situations and were often living in poverty, and everything I thought I knew, both conceptually and intellectually, fell apart. That was one of the biggest learning experiences I had. I learned that a lot of my assumptions, maybe all of my assumptions, are off. I needed to go back to the drawing board.
I learned a lot about the complex lived experience of people, particularly how the intersection of history, class, race, et cetera, can inform their worldview and their behaviors. All those factors can cause us to do contradictory things, which I do myself all of the time. I learned that lesson in the field.
It really messed with me because I thought I was going to arrive at the Truth with the capital T. But I realized that although I’m still going to write this thesis, I believe in it and I have enough research to do it, I don’t know that there’s going to be a Truth at the end.
Studying in South Africa was a huge precursor to how I approach my life and my career. I learned that seeking some very black and white clear Truth or solution is often a fool’s errand and you have to seek out discomfort in order to really learn and grow.
SG: How would you describe your career and focus?
AS: I typically say that I have over 15 years experience of working across pretty much every aspect of marketing — from growth to brand to product, the whole life cycle. I’ve spent most of my career in media and consumer tech. I go really broad, but the places where I have the most expertise are brand and product marketing.
My point of view on the number one role of a marketing team, is to know the customer better than anybody else in the company. In any internal meeting, the marketing team should be able to be the voice of the customer. They should know their problems, motivations, and cultural contexts better than anybody else. If they’re not doing that, then they won’t do their jobs well. People like to say that they are customer first marketers, but what does that actually look like? Are you talking to your customers all the time? I think people say that more than they live it.
SG: How does this get away from people? How does this customer-centricity dissolve over time?
AS: The most common way that it dissolves is you get really big, really fast. All of a sudden you have a lot of different types of customers. Not only do you not know much about all of them, but you don’t know if you even want to keep all of them. Because you can not focus on certain customers, and that’s fine. But that’s a conscious choice that needs to be made. It’s not just, “Oh shoot, we didn’t build for that person.” You need to really think it through.
When companies start out, they usually know exactly who they are going after. Now it’s two years later — we have a lot of customers, the product’s changed, the world’s changed, and we’ve never checked back in. We don’t know who all these people are. We also don’t have consensus on who we really want using this, nor do we really know who is using this.
SG: If you get there, how do you call a timeout within the organization? Acknowledge that we’ve lost the thread here and there’s a lot of competing interests. What do you do to turn back the clock to that moment when you actually were connected?
AS: When that happens, most people in the organization agree that that is what’s happening. It doesn’t take much to convince people that it’s a problem. That’s the good part.
The hard part is how you solve for the problem. Because you’ve got a bunch of different stakeholders who have different opinions about who the customer is you need to go after and why, and who doesn’t matter and why. That’s when it becomes a real strategy exercise. Because you need to identify where the company is going in the next. In the next three to five years, what are you growing into? What do you want to be in the world? Who are the people in the world that are going to be the most excited about that? You need to be able to articulate that.
There are concentric circles outside of that 10%, but you better know who that 10% is. I would imagine it’s much like political organizing. Who’s your base? You need to know who your base is. Then you can say, this isn’t our base, but they’re about 10% removed, so we’re aligned on a bunch of stuff here. Let’s go there first and then maybe you go a little farther out. When you’re doing an exercise like that, you absolutely have to have the CEO on board. It has to come from the top. That person needs to be involved or it will fall apart. Because it really needs that level and stamp of approval. Without that, it just won’t get implemented. Or you may see infighting between teams and other things that just aren’t productive.
Another thing that’s been helpful is just really good research. The truth seems more obvious when it’s coming out of the mouth of a customer than it does when it’s coming out of my mouth. When you start to hear the same thing again and again and again, people will take that stuff a lot more seriously than me just diagnosing the problem.
SG: What happens when you have a CEO that says, “Customers just don’t get it. I know the big vision here, they’ll catch up to it. It’s less about me and it’s more about their lack of imagination.”
AS: Then you don’t have a business yet. You have a vision. Because a business has customers who know what to use it for and how to find value out of it.
SG: So when you look back to your time in South Africa at all these different stops along your career, how do you connect that experience to being inside somewhere like Foursquare or Medium?
AS: Being comfortable with ambiguity is something that I’ve had to teach myself and learn. It’s not something that comes naturally to me. When I look back at that time, it was one of the first times that I really had to deal with that. At startups, and at any company that’s doing something net-new, you have to figure out how to be at ease with more questions than answers. And I don’t like it all the time.
As a person, I have always been interdisciplinary in nature. When I look at my career now and all the different things that I’ve done, I see that my most natural state is connecting the dots between ideas and people. As I like to say, I’ve always been a little bit blobby.
And that can be useful in small teams that need to work fast. I can quickly pull together a lot of people and disparate ideas and distill what’s in front of us to create some semblance of a strategy to move us forward. I can bring a little bit of structure, texture, and clarity to the things that everybody’s discussing in private one-on-one conversations, in small group conversations, and in department meetings. I’m always trying to pull that together at a company wide level so that we’re all speaking the same language and we’re all identifying the same challenges.
SG: Let’s get into the blobby. Being blobby is shorthand for, I do a lot of things and it’s hard to pin me down. But why isn’t there a title for what you do? The ability to bring together disparate parties within an organization, to dig into the truth, to come up with a strategy, to connect it with marketing or product or whatever. Why is this thing ambiguous and why are we afraid of defining it?
AS: Organizations are very highly practical. In my experience, the bigger they are, the more pragmatic they get. Either you own a P&L or you don’t. It’s harder to figure out where these more ambiguous roles fit. They want to be able to place you in a very specific part of the org that pushes a very specific metric that allows them to say, “You were successful” or “You were not successful” in these very tangible ways. I understand the want for that, having led teams. Some of that is just pragmatic in the way that organizations are built.
What do you think?
SG: It’s an existential question for me, too. This role exists in many companies, someone who can be this universal translator, problem solver, fixer, and harmonizer. That person could sit in a lot of different places. Frankly this is the opportunity that people in comms/brand really have, because they are connected. They’re also required to be focused on the truth, they’re not focused on some fantasy version of the organization. Because if you operate in a fantasy land, you can’t do your job. You have to connect, you have to listen to people, because you have to figure out what the hell is going on and what’s actually the reality of the situation. Because you don’t want your communications to get beyond that or ahead of it.
That facilitative role, some might call it family therapy, there’s something to that. This is a core component of what we do. And if you’re really good at it, this is important stuff. This is equal to, if not more important, than some unicorn 10x engineer. To be able to diagnose issues internally, come up with solutions, bring people together to solve them, and then be able to turn that into outbound marketing or communications that’s resonant with the market — that is a pretty powerful thing.
The collective we, we sell ourselves short on that. It’s an incredibly strategic skill. There are many management consultants who are paid lots of money to go through and “optimize” the business and come up with the right spreadsheet structure on how to save money, in terms of creating efficiencies. But this is doing that on a much more profound level. It’s actual human optimization — getting teams working together, individuals working together, and then taking all this disparate ambiguity and inputs and then learning where you’re wrong.
Because more often than not, everyone walks into these organizations with an assumption, the same way you showed up in Cape Town. Everyone walks into a new job saying, “This is awesome. I can’t believe this great company with this incredible mission is doing all these amazing things.” And then the inevitable occurs and reality sets in. The question becomes, what do you do with it? Do you just recoil or you can be a problem solver?
And no one hires for this role, they hire for something else. Like if you were to sell yourself as a consultant, you’d probably say, “I do marketing, go to market, product marketing, et cetera.”
AS: That’s exactly what I say.
SG: Let’s talk about failure. I don’t think it’s as taboo as it once was, there’s been a lot more willingness to discuss it. A lot of people listen to Brené Brown’s podcasts. But what’s your view on failure as a way to evolve yourself? How does it shape you as also a person and a practitioner?
AS: We’ve gotten better at talking about it and it being socially acceptable, but I wonder if we’ve gotten better at actually feeling okay about it. Speaking for myself, I still don’t feel very good about it. Even though I know it’s okay to fail and actually it’s good to fail. If you talk to a scientist, they’re like, “All we do all day long is fail. And hope eventually one of these things works.”
I don’t know very many people, and I’m putting myself first here, that actually know how to live with failure and feel okay about it. Personally, I always still feel like something is wrong with me, or that I haven’t worked hard enough, smart enough, or whatever the case may be. But I’m intellectually good about it. Like if you went through a list of all your failures, I would be like, “That’s amazing. You’re still an amazing smart person.” I would never judge you. I would think you were still the same smart person I met at the beginning of this conversation. But for me to feel that about me, is incredibly challenging.
I think a lot about the practices that I need to put into my own life to actually be truly at peace with failure — or perceived failure or inadequacies or perceived inadequacies. As a side note, part of that is really what led me into yoga, I’m a certified yoga teacher. That is a piece of what needs to be a larger toolkit when I think about how I metabolize my own beliefs. I don’t find that I’m always doing that. It’s so much easier to do it for other people than for yourself.
SG: When we think about this in terms of organizations, how do we create these kinds of conversations internally? Maybe it’s not about the P&L, reaching our customers, or the metrics, maybe the CEO is just scared of failing. Their last company failed, or they had to fire 20% of the team last week and they are totally freaked out about that. They are not managing well because of this traumatic experience. So how do we take this self-analysis and apply it to the humans at work? Especially in leadership positions? There’s so much theater you can do around problem solving, when actually, the problem is often much more internal.
AS: It’s funny how quickly we forget that organizations are just people. We’re just a bunch of people hanging out and trying to do something together. That’s it. The poet David Whyte has this great line “Your great mistake is to act the drama as if you were alone.” And what I take him to mean by that is that every person in your life, every object, every experience is in this whole chaotic cosmic dance with you. If that’s true, and I believe it is, how does that affect how you show up in the world? And specifically how you show up in hard times?
I think that even when you’re not a “leader” at a company, how you show up is more important than literally anything else you’re doing. Anything. And we don’t learn that in school, we’re not told that, we’re typically not rewarded for it in any sort of tangible way. But I do firmly believe it. How you show up in every room and every conversation, how you create space for people to be honest and speak up, how you create opportunities for laughter and perspective and humanity — that creates the most amount of impact.
When companies have a good culture with great leaders who create truly open spaces and are able to bring both confidence and levity in times when people are stressed, and get them out of a place of fear and back into a high functioning place — those are the companies that will thrive in the modern workplace, in my opinion. They’ll be able to have big, tough conversations and come out stronger and better.
SG: If there’s a young Ashley Simon out there, who is the first marketing hire at a startup tasked with all the marketing things. What’s your advice to that person on how to think about their job and how to navigate their career?
AS: My marketing advice, especially for new young companies and first marketers in, is if you don’t have a lot of money, you better have a point of view. Know who you are and what you’re for and stand firmly in it.
My advice on how to show up, is to work hard and be kind. I love that Conan line because it’s just never going to fail you. You’re never going to be mad at yourself for working hard or being kind. You’re never going to look back at your career and regret that moment when I was really nice to that person, or when I worked an all-nighter to get something out the door that I really cared about and I know is important to other people. Just work hard and be kind.
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