From Field to Glossier, and Comms to Enterprise Capital, Ashley Mayer Is Carving a Fairly Distinctive Path. What She’s Discovered, And What You Can Be taught From Her.
We had overlapping circles after which grew to become mates. I’m an Ashley Mayer superfan so past the affinity, have been lucky sufficient to additionally carry her into Homebrew as an advisor to our portfolio firms, and spend money on Coalition, a enterprise agency she based together with three different superb feminine operators. Her private story and insights into tech are helpful and novel, therefore why I requested her to share them with you, in 5 Questions.
Hunter Stroll: Okay, so we first met while you have been main comms at enterprise software program firm Field, a startup you joined once they have been nonetheless fairly early and stayed at till post-IPO. First, congrats! However second, I spotted I truly don’t know the story of the way you first got here throughout Field and why you determined to affix. After which take your expertise and switch it into a bit of thought management profession recommendation to share with folks studying this 🙂
Ashley Mayer: I used to be two years post-college and dealing at a public relations company in San Francisco, a job and profession path I stumbled onto once I was rejected by my high legislation faculty picks. I wasn’t significantly good at or impressed by the function, however then I labored with my first startup shopper and was immediately seduced by the power and audacity of that venture. Higher Place was constructing the charging infrastructure to allow mass adoption of electrical automobiles; it was led by a charismatic CEO, raised gobs of capital earlier than that was the norm, and later imploded spectacularly. I attempted to get employed at Higher Place and failed. However for the primary time since abandoning my legislation faculty plan A, my mandate was clear: I wanted to work at a startup.
Enter Field. I had gone to highschool with the founders within the Seattle space, and we had lately reconnected. After I realized they have been hiring a group supervisor, I threw every little thing I had on the interview course of. They gave me a shot.
Working at Field was a revelation. I had come out of an setting with quite a lot of hierarchy, the place everybody was doing variations of the identical job. Field had simply 50 staff and was hitting an inflection level once I joined in 2009, so there was way more work to do than folks to do it. My boss, Jen Grant, was an unimaginable supervisor, and Aaron Levie, the co-founder and CEO, was a incredible accomplice on all issues communications. Each milestone was a chance to inform the largest potential story.
With the advantage of hindsight, I’m glad I spent these first two years feeling considerably misplaced, career-wise. There’s quite a lot of strain to construct the right resume proper from the beginning, however as soon as I’d failed that task, I used to be free to optimize for various issues, like studying and having enjoyable.
My recommendation to folks early of their profession is fairly easy: your mission isn’t to pursue a profession, it’s to find it. Put your self in fascinating conditions. Every expertise is a constructing block and, sooner or later, you’ll determine the best way to prepare (and rearrange) all these blocks in ways in which make sense for you. Folks with spectacular careers might sound like they have been strategic all alongside, however I’m satisfied that typically, that’s solely as a result of they’re wanting backwards. Particularly within the unpredictable and fast-moving world of startups, careers are tales that solely make sense in hindsight.
HW: Anybody who’s been by an IPO, I all the time wish to ask in regards to the expertise as a result of it’s such a basic, if statistically uncommon, startup milestone. I assume main Comms you actually needed to be cautious in the course of the quiet interval and so forth, all whereas letting Aaron nonetheless be Aaron. Any good tales or reminiscences in regards to the course of or itemizing day itself?
AM: Attending to work on the Field IPO was one of many coolest issues I’ve ever executed. It was additionally one of many hardest. We initially filed to go public in March of 2014, and didn’t truly turn out to be a public firm till January of 2015. A course of that usually takes 5 weeks, give or take, took us ten months! Our timing was brutal: the Field S-1 coincided with the beginning of a significant market correction for SaaS shares, and our newly revealed financials made us a pure poster firm for that change in sentiment.
Till then, Field’s narrative had been constantly up and to the fitting. We have been fascinating sufficient to be newsworthy, particularly since Aaron was such a compelling spokesperson for the evolving enterprise software program class, however we hadn’t attracted the identical degree of skepticism as our buzzier, extra extremely valued client contemporaries. So when public notion of Field modified in a single day, I wasn’t ready, emotionally or strategically. Years later, I wrote about a number of of my hard-won classes from Field’s IPO course of.
Two further moments stand out to me. The primary was in July of 2014, after we made the bizarre transfer of elevating and asserting one other spherical of personal financing whereas on file to go public. We might have simply left the information cycle at that, however determined to proactively launch our Q1 numbers in tandem to indicate our progress, like a mini earnings. I keep in mind on the final minute we had a disaster of confidence…was this actually the fitting transfer? May we nonetheless belief our instincts? We solid forward, and reception was constructive. Placing out these numbers didn’t magically repair our story, after all. Field’s ten-month quiet interval taught me that rebuilding belief and confidence is one thing that occurs incrementally. We continued to report our financials each quarter main as much as the IPO, and by the point we have been lastly able to go public, folks had a a lot better understanding of our enterprise fundamentals and trajectory.
The second second was the IPO itself. I keep in mind feeling oddly calm amidst the clamor of the NYSE buying and selling room flooring. I used to be on the balcony with my colleagues for the bell ringing, and through all that clapping and cheering, I felt a wave of gratitude for all we had skilled to get to that milestone. It was clear to me that this crew and firm have been so a lot better ready for no matter was forward as a result of we’d been by one thing exhausting, and had made it to the opposite facet with a deeper resolve and thicker pores and skin. At any time when I’m at a profession low level, I’m going again to that second.
HW: Then you definitely did a little bit of a Enterprise (Social Capital, another person’s agency) -> Glossier -> Enterprise (Coalition Operators your individual agency) loop. Social Capital has clearly advanced from its authentic type and that was the interval the place you moved on, so I wish to deal with the choice to return to working. Field and Glossier really feel like two very totally different industries! Are they type of just like the ‘two sides of Ashley’ or are they really extra comparable (from the attitude of your function: work with a compelling founder/CEO, assist different folks perceive what’s particular in regards to the firm, and so forth)?
AM: I like switching between an working view (depth) and an ecosystem view (breadth): it’s the one constant sample in my profession! Working retains you trustworthy, whereas attending to work throughout a number of firms and classes provides you perspective. It’s a strong mixture, and I later realized I might have my cake and eat it too once I began investing and serving as a Homebrew Advisor whereas main Comms at Glossier.
I used to be initially going to take break day after leaving Social Capital, and even attempt to write a e book (one thing that’s nonetheless on my bucket record). However an off-the-cuff espresso with Emily Weiss on the eve of my final day at Social Capital in the end modified these plans. I joined Glossier due to all of the issues I hoped I might study: about client companies, the sweetness {industry}, model and group constructing, and past. After working for 2 male CEOs, I used to be able to help a visionary feminine chief, and hoped I might have the ability to problem and develop conventional founder archetypes by my work at Glossier.
Moreover, my Field expertise taught me that I cherished telling tales of class transformation, and that changing into a poster firm for an evolving class can create main narrative tailwinds for a enterprise. I believed possibly Glossier can be one other alternative for that kind of story — both in magnificence particularly, or e-commerce extra broadly.
HW: You constantly communicate out while you see feminine CEOs get handled otherwise by the press. Not that CEOs are above criticism or evaluation, however that there are profile tropes which appear fairly gendered and don’t get utilized to male leaders in the identical manner. How do you assist feminine leaders navigate this potential bias? I’m significantly fascinated by how language as soon as used supportively for empowerment by some feminine CEOs (#girlboss) can then be used negatively by media and detractors afterward. The reply can’t simply be “keep very boring” proper?!?
AM: The factor that worries me essentially the most is the hidden industry-wide toll these tales take. I’ve heard from too many founders, together with these on the very earliest phases of firm constructing, who’ve learn these articles about a number of the most seen ladies in our {industry} and really feel like they have already got a goal on their backs. That’s a heavy burden to hold when your job is to push boundaries and break with the established order.
Thankfully, I don’t assume the trail ahead is to “keep very boring.” Perhaps that is my inherent bias as a comms professional, however in combination, I imagine the uncaptured upside when ladies founders keep below the radar is much extra detrimental than the dangers that include visibility.
For any particular person founder, all comms choices ought to begin with the specified enterprise impression. Which viewers do we have to attain, and what do we would like them to do? For some early stage startups, investing in comms received’t meaningfully transfer the needle; for others, it may be transformative. Framing profile constructing choices when it comes to enterprise targets not solely makes this facet of the job extra palatable for founders who aren’t publicity inclined, it additionally makes it simpler to weigh potential dangers towards potential rewards.
These choices turn out to be extra nuanced with visibility and success, when ladies and different underrepresented founders are invariably held up as symbols of their respective identities. Deciding whether or not to embrace this facet of profile constructing, and any of the “girlboss” kind lingo that comes with it, is each an expert and deeply private calculation. What’s important is that founders are ready for the extra scrutiny this consideration will carry, whether or not or not they search it out. Investing in inner communications, constructing out owned channels, and figuring out advocates who will name out unfair therapy once they see it (a job we should always all play if we are able to afford to) give founders a stronger basis as spokespeople for firms, classes and actions.
After all, media scrutiny doesn’t exist in a vacuum. Many of those tales, and the anecdotes that form them, are a mirrored image of the best way society as a complete views ladies in positions of energy. In the present day, my finest recommendation is to be ready, and when issues get powerful, for founders, boards and comms groups to take a deep breath and never overreact (I might write a complete weblog publish on this). However what I really need for this subsequent era of founders isn’t only a good protection. I wish to see ladies on offense: taking dangers with daring concepts, and experimenting with new methods to get them in entrance of individuals. I assume we’ll know we’ve made it when a girl can get away with behaving like Elon Musk.
HW: You lately launched Coalition Operators, a enterprise agency + operator/advisor community to actually assist startups with extra than simply capital. I’ve seen your work firsthand since we’ve been fortunate sufficient to have you ever as an Advisor to Homebrew’s portfolio. What satisfied you — and your different companions — that this was the subsequent part of your profession? What kind of alternatives are you most fascinated by?
AM: Angel investing was our collective gateway to constructing Coalition. We have been all at totally different factors in that journey, and in early 2020, we began investing along with pooled scout capital from Thrive Capital. We every have totally different purposeful and sector experience, so this was a chance to study with and from each other whereas supporting early stage firms, alongside our core jobs as founders (Toyin Ajayi at Cityblock, Jackie Nelson at Tribe AI, Lindsay Ullman at Umbrella) and operators (I used to be working comms at Glossier).
Within the technique of investing, we grew to become fairly obsessive about serving to founders construct extra numerous and impactful cap tables. We’d all benefited tremendously from accessing scout capital…might we create a brand new mannequin to carry extra ladies into this a part of the startup ecosystem at scale? So in 2021, we partnered with Thrive and Basic Catalyst to attach wildly gifted operators and startups of their portfolios, with the VC companies sharing a portion of their potential upside in alternate for advisory help.
Now in 2022, we’ve taken each of those efforts to the subsequent degree. We lately introduced Coalition Fund I, a $12.5M early stage fund (our candy spot is Seed and $200–300K investments), and the Coalition Community, a spot the place high operators can take a “portfolio strategy” to their careers and construct their wealth and impression past their day jobs. We’re unsurprisingly very founder pushed in our investing, and whereas we’re class agnostic, focus quite a lot of our time in areas the place we’ve got expertise constructing, together with healthcare, future of labor, e-commerce, marketplaces, and local weather. We’re additionally continually assembly with unimaginable operators, and along with the mannequin we’ve created with Thrive and GC, love pulling them into offers alongside us as angel traders. We’ve principally constructed the merchandise we’ve all the time wished for ourselves as founders and operators.
That is now my full-time job (my companions are part-time as they run their firms), and I’m nonetheless in awe of how I get to spend my days. For me, this was essentially the most natural and apparent profession transfer I’ve made thus far, despite the fact that it’s additionally my greatest pivot and I’ve a lot to study. Once you spend your nights and weekends constructing one thing you care quite a bit about, getting to offer it your full power and a focus is an unimaginable privilege.
Thanks Ashley, wanting ahead to working with you and Coalition!
