From Field to Glossier, and Comms to Enterprise Capital, Ashley Mayer Is Carving a Fairly Distinctive Path. What She’s Realized, And What You Can Be taught From Her.
We had overlapping circles after which grew to become pals. I’m an Ashley Mayer superfan so past the affinity, have been lucky sufficient to additionally convey her into Homebrew as an advisor to our portfolio firms, and put money into Coalition, a enterprise agency she based together with three different superb feminine operators. Her private story and insights into tech are worthwhile and novel, therefore why I requested her to share them with you, in 5 Questions.
Hunter Stroll: Okay, so we first met whenever you have been main comms at enterprise software program firm Field, a startup you joined after they have been nonetheless fairly early and stayed at till post-IPO. First, congrats! However second, I noticed I really 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 chunk of thought management profession recommendation to share with individuals 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 prime regulation college picks. I wasn’t significantly sensible 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 challenge. 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 regulation college 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 just lately reconnected. Once I realized they have been hiring a neighborhood supervisor, I threw the whole lot I had on the interview course of. They gave me a shot.
Working at Field was a revelation. I had come out of an atmosphere with numerous 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 individuals to do it. My boss, Jen Grant, was an unimaginable supervisor, and Aaron Levie, the co-founder and CEO, was a improbable associate on all issues communications. Each milestone was a chance to inform the largest attainable story.
With the good thing about hindsight, I’m glad I spent these first two years feeling considerably misplaced, career-wise. There’s numerous strain to construct the proper resume proper from the beginning, however as soon as I’d failed that project, I used to be free to optimize for various issues, like studying and having enjoyable.
My recommendation to individuals 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 tips on how 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 usually, that’s solely as a result of they’re trying 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 way of an IPO, I at all times prefer to ask concerning the expertise as a result of it’s such a traditional, if statistically uncommon, startup milestone. I assume main Comms you actually needed to be cautious through the quiet interval and so forth, all whereas letting Aaron nonetheless be Aaron. Any good tales or reminiscences concerning the course of or itemizing day itself?
AM: Attending to work on the Field IPO was one of many coolest issues I’ve ever accomplished. It was additionally one of many hardest. We initially filed to go public in March of 2014, and didn’t really develop into 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 persistently up and to the best. 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, once we made the weird transfer of elevating and asserting one other spherical of personal financing whereas on file to go public. We may have simply left the information cycle at that, however determined to proactively launch our Q1 numbers in tandem to point out our progress, like a mini earnings. I bear in mind on the final minute we had a disaster of confidence…was this actually the best transfer? May we nonetheless belief our instincts? We cast forward, and reception was optimistic. 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, individuals had a significantly better understanding of our enterprise fundamentals and trajectory.
The second second was the IPO itself. I bear in mind feeling oddly calm amidst the clamor of the NYSE buying and selling room ground. 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 staff and firm have been so significantly better ready for no matter was forward as a result of we’d been by way of one thing arduous, 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 am 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 unique kind and that was the interval the place you moved on, so I wish to concentrate on the choice to return to working. Field and Glossier really feel like two very completely different industries! Are they form 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 individuals perceive what’s particular concerning 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 sincere, whereas attending to work throughout a number of firms and classes offers you perspective. It’s a robust mixture, and I later realized I may 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 day without work after leaving Social Capital, and even attempt to write a guide (one thing that’s nonetheless on my bucket checklist). However an informal 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’d be taught: about client companies, the sweetness {industry}, model and neighborhood constructing, and past. After working for 2 male CEOs, I used to be able to help a visionary feminine chief, and hoped I’d be capable to problem and develop conventional founder archetypes by way of my work at Glossier.
Moreover, my Field expertise taught me that I liked 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 perhaps Glossier could be one other alternative for that sort of story — both in magnificence particularly, or e-commerce extra broadly.
HW: You persistently communicate out whenever 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 keen on how language as soon as used supportively for empowerment by some feminine CEOs (#girlboss) can then be used negatively by media and detractors in a while. The reply can’t simply be “keep very boring” proper?!?
AM: The factor that worries me probably 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 girls 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 suppose the trail ahead is to “keep very boring.” Perhaps that is my inherent bias as a comms professional, however in mixture, I imagine the uncaptured upside when girls founders keep beneath the radar is way 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 by way of 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 in opposition to potential rewards.
These choices develop into extra nuanced with visibility and success, when girls 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” sort 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 convey, whether or not or not they search it out. Investing in inside communications, constructing out owned channels, and figuring out advocates who will name out unfair therapy after 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 an entire views girls in positions of energy. At this time, my greatest recommendation is to be ready, and when issues get robust, for founders, boards and comms groups to take a deep breath and never overreact (I may write an entire weblog put up on this). However what I really need for this subsequent technology of founders isn’t only a good protection. I wish to see girls on offense: taking dangers with daring concepts, and experimenting with new methods to get them in entrance of individuals. I suppose we’ll know we’ve made it when a lady can get away with behaving like Elon Musk.
HW: You lately launched Coalition Operators, a enterprise agency + operator/advisor community to essentially 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 following part of your profession? What sort of alternatives are you most keen on?
AM: Angel investing was our collective gateway to constructing Coalition. We have been all at completely different factors in that journey, and in early 2020, we began investing along with pooled scout capital from Thrive Capital. We every have completely different useful and sector experience, so this was a chance to be taught 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 somewhat obsessive about serving to founders construct extra numerous and impactful cap tables. We’d all benefited tremendously from getting access to scout capital…may we create a brand new mannequin to convey extra girls 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 following degree. We just 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 prime 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 numerous our time in areas the place we’ve expertise constructing, together with healthcare, future of labor, e-commerce, marketplaces, and local weather. We’re additionally continuously 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 buyers. We’ve principally constructed the merchandise we’ve at all times 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 probably the most natural and apparent profession transfer I’ve made to this point, though it’s additionally my largest pivot and I’ve a lot to be taught. While you spend your nights and weekends constructing one thing you care rather a lot about, getting to provide it your full power and a focus is an unimaginable privilege.
Thanks Ashley, trying ahead to working with you and Coalition!
