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 Study From Her.

We had overlapping circles after which turned associates. 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 corporations, and spend money on Coalition, a enterprise agency she based together with three different wonderful feminine operators. Her private story and insights into tech are beneficial and novel, therefore why I requested her to share them with you, in 5 Questions.

Hunter Stroll: Okay, so we first met while you had been main comms at enterprise software program firm Field, a startup you joined after they had 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 bit 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 prime regulation faculty 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 mission. Higher Place was constructing the charging infrastructure to allow mass adoption of electrical autos; 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 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 not too long ago reconnected. Once I realized they had been hiring a neighborhood supervisor, I threw every 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 loads of hierarchy, the place everybody was doing variations of the identical job. Field had simply 50 workers 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 unbelievable supervisor, and Aaron Levie, the co-founder and CEO, was a unbelievable accomplice on all issues communications. Each milestone was a possibility to inform the most important attainable story.

With the advantage of hindsight, I’m glad I spent these first two years feeling considerably misplaced, career-wise. There’s loads of stress 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 attention-grabbing conditions. Every expertise is a constructing block and, sooner or later, you’ll determine easy methods to organize (and rearrange) all these blocks in ways in which make sense for you. Folks with spectacular careers could sound like they had been strategic all alongside, however I’m satisfied that usually, 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 means of an IPO, I at all times wish to ask in regards to 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 throughout the quiet interval and so forth, all whereas letting Aaron nonetheless be Aaron. Any good tales or recollections 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 really change 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 correct. We had been attention-grabbing 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 stage of skepticism as our buzzier, extra extremely valued shopper 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 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 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 correct transfer? Might we nonetheless belief our instincts? We cast 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 had 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 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 workforce and firm had been so a lot better ready for no matter was forward as a result of we’d been by means of one thing onerous, 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 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 developed from its authentic kind and that was the interval the place you moved on, so I need 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 in regards to the firm, and so forth)?

AM: I really 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 corporations and classes offers you perspective. It’s a strong mixture, and I later realized 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 off after leaving Social Capital, and even attempt to write a guide (one thing that’s nonetheless on my bucket listing). 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’d study: about shopper 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 of problem and broaden conventional founder archetypes by means 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 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 converse 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 method. How do you assist feminine leaders navigate this potential bias? I’m significantly curious about 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 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 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.

Happily, 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 girls founders keep beneath 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 wish them to do? For some early stage startups, investing in comms gained’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 towards potential rewards.

These choices change 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” 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 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 remedy 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 corporations, 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 best way society as an entire views girls in positions of energy. Immediately, 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 publish on this). However what I really need for this subsequent era of founders isn’t only a good protection. I need 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 girl 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 section of your profession? What kind of alternatives are you most curious about?

AM: Angel investing was our collective gateway to constructing Coalition. We had 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 purposeful and sector experience, so this was a possibility to study with and from each other whereas supporting early stage corporations, 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 operating comms at Glossier).

Within the technique of investing, we turned somewhat obsessive about serving to founders construct extra various 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 Normal Catalyst to attach wildly proficient 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 stage. We not too long ago 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 method” 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 loads of our time in areas the place we have now expertise constructing, together with healthcare, future of labor, e-commerce, marketplaces, and local weather. We’re additionally consistently assembly with unbelievable 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 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 corporations), 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, despite the fact that it’s additionally my greatest pivot and I’ve a lot to study. If you spend your nights and weekends constructing one thing you care lots about, getting to provide it your full power and a focus is an unbelievable privilege.

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