Ashley Mayer on Getting More Comms Leaders onto Cap Tables
Mixing Board Studio Session
Ashley Mayer is the cofounder and GP of Coalition Operators, where she and her partners back early stage founders. She began her career at enterprise software company Box, where she led global communications from a 50-person startup through IPO. She then moved to Social Capital, where she led all things marketing and communications for three years, helping to launch new capital products and working with founders spanning healthcare, aerospace, climate, fintech, enterprise and education. Most recently, she led communications at New York based beauty company, Glossier.
Ashley has also been a key advisor to Mixing Board since before its official inception and serves on the organization’s operating council.
In this Studio Session, Ashley and Mixing Board Founder Sean Garrett talk about making the career transition from comms to investing; why comms folks are uniquely valuable on cap tables; what a company needs to become the voice of a category; and, how people just getting started in comms should think about building a career.
SG: Tell us about what you’re doing now and how you shifted into venture from a decorated career in comms?
AM: I am a co-founder and general partner at Coalition Operators, an early stage fund and operator network. I should be honest that my move from communications to venture capital was not part of some grand career scheme. Even back when I worked in venture as a marketing partner, I didn’t imagine a future for myself as a professional investor. Angel investing was my unintentional gateway.
A big part of my job at Social Capital was spending time with founders in our portfolio, mostly Seed and Series A stage, helping them figure out how to tell their stories and build awareness. When I joined Glossier as VP of Comms shortly before our first unicorn fundraise, I loved having all those resources and momentum, but missed working with founders at the earlier stages of company building.
I had a few friends who were active angels, and they essentially peer pressured me into writing my first angel check. I loved it. It’s such a unique relationship to have with a founder, to have skin in the game and learn from them as they navigate uncharted territory. And with a comms background, it’s pretty easy to be helpful. Just demystifying how the media world operates can be impactful.
Things snowballed pretty quickly on the angel front when I started investing with the three women who are my partners at Coalition today. A few of us had been approached by Thrive Capital to be scouts. We proposed pooling that capital and creating a scout fund of sorts. We all had different functional and sector expertise, different networks, and really just loved looking at and supporting companies together.
Our first year, in 2020, we were focused on scout investing but also couldn’t stop thinking about the opportunity to bring more operators onto cap tables. Especially women and women of color, who we did not see represented in most of the deals we were doing. So in 2021, we piloted a new model to bring top operators onto cap tables at scale, in partnership with two firms, Thrive Capital and General Catalyst, while continuing to invest in parallel.
I left my job at Glossier later that year and candidly wasn’t sure what I would do next. I knew it probably wasn’t another communications role. I started spending more time on Coalition, and as I took stock of both the investing side of things and the incredible network of top women operators we were building, it became clear that we had something pretty special going, and it deserved my full time and attention. We raised a fund at the end of 2021, beginning of 2022.
When I was fundraising, a few people asked me, “Why start your own firm instead of joining an established VC firm?” And the honest answer is that the latter hadn’t even occurred to me. So much of the decision to go all-in on building Coalition was about the people. Not just my partners, who are amazing, but also the founders and operators we were getting to work with. Once I saw the path, even though it was a big pivot for me, it felt inevitable.
SG: Comms, marketing, and brand folks often ask: How do I make this journey to being an investor or having skin in the game through advisory work? How do people best cross that transom to get on the cap table? How do you make that ask? It’s a leap that a lot of people don’t make, just because they don’t know what questions to ask.
AM: I have a lot of empathy for people in that position. Even though I was pretty embedded in the startup ecosystem and knew so many founders, it wasn’t like people were asking me to invest in or advise their companies — until I made my first investment, and the momentum built from there.
There’s often a mismatch between the people who have both access to deals and capital to deploy, and the people who have the skills and experience that would be most valuable for a particular startup. Many of the most impressive people in the startup world are in that latter, much larger bucket. They’re heads down on their core jobs, and either don’t know how to get started as investors or advisers, or don’t feel welcome.
If you’ve built a monster startup career, the process of finding relevant advisory roles, potential angel investments, and even board seats should be pretty straightforward. But because this part of the ecosystem is so opaque and network driven, it’s really not. This sucks equally for the founders who would benefit enormously from operational expertise, but are limited by their own networks and the need to get through fundraising and back to building as quickly as possible. It’s an access problem in both directions.
We need new models to connect operators with startup opportunities, especially groups who are currently under-activated. That’s what we’re focused on with the Coalition Network, where we bring top women operators into deals where their expertise is uniquely relevant, with no personal capital required and full upside exposure (our VC partners share their economics). There are other cool examples, like Operator Collective, which taps its operator LP base for portfolio-wide support, and Modern Angels, a group of women and non-binary angels, curated by a partner at Cowboy Ventures.
The good news is that there’s a ton of demand for comms, brand and marketing expertise, since founders rarely have those roles on their teams early on. I’d encourage anyone with these skills to be direct with founders about their interest in working for equity, especially in this current market, where cash is precious. VCs are another great channel, since they’re regularly helping founders fill out rounds and address gaps on their teams.
SG: How does one even know how to do it? When you’re doing advisory deals, how do you structure the terms? Is that something that you are sharing and helping people understand at Coalition? The fundamentals of this stuff?
AM: It’s tricky because advisory relationships really run the gamut from super hands-on to more consultative. And of course, founders can feel differently about giving up equity. One of the things we’ve done with the Coalition Network is standardize the economics and remove that friction from the process. Operators and founders can focus their attention on whether or not it’s a good match, in terms of impact to the business, chemistry, capacity, etc.
Angel investing is a little easier. You basically decide what amount you’re personally comfortable investing, and whether you’re okay with the terms of the deal, which are set by someone else. In my experience, founders are always willing to take small checks from people who they think will be helpful.
SG: When you originally started writing checks and the word got around that you were doing this stuff, a large part of that is because people know who you are and what you personally can bring to the table, which is considerable. You brought this unique perspective of having been a leader at an enterprise tech company, in venture marketing, and at a big global consumer brand like Glossier. And you’re bringing all this from a comms and marketing perspective. What about the comms part were people valuing? And why was that different or additive?
AM: The comms piece was what founders valued the most. And that’s because there simply aren’t a lot of ways to get good, affordable comms advice early on.
Founders are very aware of the areas where they have blind spots. And because most of my angel investments, and now fund investments, were seed stage, they weren’t going to have anyone on their early team who had a comms background. They often didn’t even have a marketing person yet. The comms hire is going to come much later. And it’s probably too early to work with an agency.
A founder’s job is to always think a few steps ahead, so it’s pretty easy to see where comms expertise is going to be useful during a fundraise, since one of the first things they’ll do once the round is closed is decide whether to announce the new funding and how to get the most out of that moment.
SG: Or even theoretically, as you fundraise too.
AM: Giving founders feedback on the pitch itself is the best! But I often find myself holding back, because it’s a sensitive thing if you’re meeting someone for the first time, and especially if you already know the company isn’t a fit for you. When founders ask for feedback, though, I’m always thrilled because that’s such a fun mode to get into with someone.
SG: What is it about having a comms background and filter? How does that help you invest? What are you seeing that maybe other people aren’t seeing? Or what are you hearing, more importantly, that other people don’t hear when you’re talking to a founder?
AM: Having a comms background is great when it comes to helping founders in our portfolio, because I’m usually the only investor on their cap table with that skill. I would say it’s both a strength and a weakness when it comes to making investment decisions. The part that is really easy for me is seeing the biggest possible future for any startup I get excited about. My brain just goes there, and I’m sure founders can sense my genuine enthusiasm. Sometimes, I see a bigger story than the one the founder is pitching. I’ve had to train myself to slow down, examine my assumptions and think from first principles.
SG: Now that you’re deep into investing as your full-time job, if you get a question from a founder that’s comms related, how has your perception changed since you were wearing a purely comms hat? Is there anything that’s evolved or changed for you?
AM: I’ve always tried to be really honest with founders about whether or not comms will be a big lever for them in the foreseeable future. Early on, their number one job is to find product-market fit, and prioritize their time and resources ruthlessly in service of that goal. More often than not, I find myself advocating for a precision approach to awareness building, making the most of a big moment like a fundraise or a product launch, and getting really crisp on who the target audience is.
But there are definitely some companies where I tell the founder, “You could become a voice for this category.”
SG: What are the characteristics of those companies?
AM: Three things. The first is that the category you’re in is going through some sort of meaningful transformation. Secondly, what you’re building is, in some way, a microcosm for that change. And lastly, the founder should have the aptitude and appetite to be that spokesperson.
If you’re lucky enough to have those three ingredients, there’s the potential to become a spokesperson and poster company for that category’s transformation, which creates incredible narrative tailwinds for your business.
I experienced this first hand at Box, because Box’s rise coincided with the explosive growth of the enterprise SaaS category. We spent far more time talking about the booming enterprise software landscape, work shifting to the cloud, and the changing role of IT than we did file sharing and collaboration. The 30,000 ft view.
I’m naturally drawn to these types of companies, and I make sure founders know when I think they might have this kind of opportunity ahead of them.
The most obvious modern example is Ryan Peterson at Flexport as the spokesperson for the supply chain crisis.
SG: It doesn’t matter if you know what Flexport does, he is just synonymous with supply chain.
AM: Exactly. And there was obviously a lot of work that got him there. There are several categories like that, where there’s an open opportunity for someone to become the voice for that change. What’s driving it? How should we feel about it? What does the future look like? That all accrues to your business, from a narrative standpoint.
SG: That’s super abundant thinking, proactive, and strategic. But then you slip on the banana peel of the current economic environment, and people will say, maybe it’s just better if we don’t talk at all. We’ll just go under our rock for nine months and see what happens while we ruthlessly refine what we do. How are you advising founders to think about comms in these times we’re in now?
AM: Being heads down is the right move for a lot of people. The most important thing is building a business that can survive this period and has a chance to come out the other side.
But there are a few silver linings in this market. From a hiring perspective, we’ll see talent accrue more efficiently to the most promising startups. And I’m also excited to see attention accrue to companies that can seize this moment.
A lot of the bigger players are pretty quiet right now. That creates more space for founders who have a story to tell. It’s going to be much easier to get attention than it was a couple of years ago when everyone was out there talking about what they were building.
SG: You’ve definitely gone on a journey to different continents of categories in your career. You were at an agency, moved into leading an enterprise tech company going public, moved into the venture world, and then going to the opposite of Box — a consumer beauty company based in New York. What do you tell young people entering into comms about that journey and what you learned? How might people apply that to their own personal careers?
AM: The thing I tell anyone who’s early in their career, whether or not they’re in comms, is don’t overthink these decisions. Your job is to collect experiences and go after opportunities that could be interesting. All of these jobs, all of these milestones — they’re building blocks. You get to decide how to arrange them later.
Anyone who’s old enough to have a handful of career chapters can talk about them in a way that sounds super strategic. I could certainly tell the story of my career as if every decision I’ve made has very intentionally led up to what I’m doing now. And the cool thing is, it does actually feel that way. But that’s not the truth. It’s a story told in hindsight.
I used to envy people who said, “I want to be a Fortune 500 CMO, so I’m going to do A, B and C to get there.” I’ve never had that career north star, but because of that, I’m in a role I never would have imagined for myself. And now, for the first time, I’m starting to think decades out, which is both scary and extremely cool. But doing that in my twenties, without any of my building blocks, without everything I’ve learned about myself over the past 15 years, would have been paralyzing.
I hope that’s freeing, especially for younger people in comms who are just getting started and see all these different career trajectories, all these different blueprints. That’s stressful, especially if you’re going to work in the startup world. There are so many unknowns. You could be getting on a rocket ship, or a sinking ship. You don’t know. But hey, you’re going to learn a lot in both scenarios! If you’re curious, if you go after interesting opportunities, and if you take the time to reflect on what all of these skills and experiences you’ve collected add up to — it will lead you to your next move. It’s more an exercise in discovery than strategy.
And to people who are further along in building a comms career in the tech industry and are looking to shake things up: don’t let people pigeonhole you. Use your expertise to broaden your professional identity, through advising, investing, writing, side projects, whatever. Comms is an incredibly strategic function, and the skills you’ve built will be relevant in literally anything that you do next. But the reality is that this industry does not believe a comms leader can do anything like it believes a product leader can do anything. You’re going to have to work harder to help the market see you in a more creative and expansive way, and you have all the tools to do it.
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