“I assume we’ll know we’ve made it when a lady can get away with behaving like Elon Musk.” Speaking With VC Ashley Mayer About Discovering Your Profession, Taking Field Public, And Why She’s Not In Studying But One other Feminine CEO Takedown

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 turned buddies. 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 put money into Coalition, a enterprise agency she based together with three different superb feminine operators. Her private story and insights into tech are useful 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 noticed I really don’t know the story of the way you first got here throughout Field and why you determined to hitch. 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 after I was rejected by my high legislation college picks. I wasn’t notably good at or impressed by the position, however then I labored with my first startup shopper and was immediately seduced by the vitality 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 legislation 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. After I discovered they have been hiring a group supervisor, I threw all the things I had on the interview course of. They gave me a shot.

Working at Field was a revelation. I had come out of an surroundings 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 after I joined in 2009, so there was much 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 accomplice on all issues communications. Each milestone was a chance to inform the largest potential story.

With the good thing about 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 proper 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 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 methods to prepare (and rearrange) all these blocks in ways in which make sense for you. Folks with spectacular careers could sound like they have been strategic all alongside, however I’m satisfied that typically, 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 via an IPO, I all the time wish 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 in the course of 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 achieved. It was additionally one of many hardest. We initially filed to go public in March of 2014, and didn’t really 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 persistently up and to the appropriate. 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 saying 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 appropriate transfer? Might we nonetheless belief our instincts? We solid forward, and reception was optimistic. Placing out these numbers didn’t magically repair our story, in fact. 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 a lot 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 a lot better ready for no matter was forward as a result of we’d been via one thing arduous, and had made it to the opposite aspect with a deeper resolve and thicker pores and skin. Every time I’m at a profession low level, I’m going again to that second.

HW: Then you definately did a little bit of a Enterprise (Social Capital, another person’s agency) -> Glossier -> Enterprise (Coalition Operators your personal 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 give attention to 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 related (from the attitude of your position: 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 provides you perspective. It’s a robust mixture, and I later discovered I may have my cake and eat it too after 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 ebook (one thing that’s nonetheless on my bucket listing). However an informal espresso with Emily Weiss on the eve of my final day at Social Capital finally modified these plans. I joined Glossier due to all of the issues I hoped I might study: about client companies, the wonder {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 be capable of problem and increase conventional founder archetypes via 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 assumed possibly Glossier can be one other alternative for that kind of story — both in magnificence particularly, or e-commerce extra broadly.

HW: You persistently communicate out while you see feminine CEOs get handled in another way 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 method. How do you assist feminine leaders navigate this potential bias? I’m notably occupied with 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 levels of firm constructing, who’ve learn these articles about among 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.

Fortuitously, I don’t suppose the trail ahead is to “keep very boring.” Possibly that is my inherent bias as a comms professional, however in combination, I consider 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 objectives not solely makes this side 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 turn out to be 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 side 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 remedy 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.

In fact, media scrutiny doesn’t exist in a vacuum. Many of those tales, and the anecdotes that form them, are a mirrored image of the way in which society as a complete views girls in positions of energy. As we speak, 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 a complete weblog publish 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 assume we’ll know we’ve made it when a lady can get away with behaving like Elon Musk.

HW: You latterly 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 occupied with?

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 practical 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 means of investing, we turned reasonably obsessive about serving to founders construct extra various and impactful cap tables. We’d all benefited tremendously from accessing scout capital…may we create a brand new mannequin to carry 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 change for advisory help.

Now in 2022, we’ve taken each of those efforts to the subsequent 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 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 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 traders. We’ve mainly constructed the merchandise we’ve all the time needed 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 so far, despite the fact that it’s additionally my largest pivot and I’ve a lot to study. Whenever you spend your nights and weekends constructing one thing you care lots about, getting to provide it your full vitality and a focus is an unimaginable privilege.

Thanks Ashley, trying ahead to working with you and Coalition!

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