Today marks one year in New York City.

Exactly one year to the day since I flew here by myself, collected the keys from my broker in the dark, went straight to Target to buy an air mattress and other essentials, and got caught in a downpour. I remember sitting in my empty living room at 10pm on a yoga mat I’d somehow deemed to be as necessary as hand soap and toilet paper but still have never properly used, completely drenched and feeling rather sorry for myself.

Image for post
Image for post

But then I changed into dry clothes and walked half a block to the neighborhood restaurant. I sat at the bar, planning to be thoroughly engrossed in my phone as I consumed two glasses of wine and the most indulgent dish on the menu. But my phone didn’t stand a chance. Over two hours I met what felt like the entire neighborhood, including a very sweet older couple who handed me a cocktail napkin with their address and insisted I “come visit anytime.” (I wish I could say I did.) And at the end of the night, I wasn’t allowed to pay for my (at least) three glasses of wine. …


Image for post
Image for post
Photo: Jared Erondu/Unsplash

Silicon Valley is a magical place with some strange norms—perhaps because companies, careers, and fortunes rise and fall with such astounding speed. Here are a few of the quirky, brutal, and hopefully useful lessons I learned during my 11 years living and working in the technology industry’s epicenter.

1. There’s opportunity in what others undervalue

There’s a rigid hierarchy of functions in Silicon Valley. At the top of the pyramid sit the entrepreneurs, the engineers, the venture capitalists. The closer you are to building or funding, the more respect you get—which probably makes sense. But when I began my career in tech, I wasn’t prepared for how little respect is left over for other functions: recruiting, HR, marketing, communications, etc. There’s an assumption that truly great products market themselves or that truly great companies are magnets for top talent. …


Image for post
Image for post
Saul Loeb / AP

So you have a big job interview coming up? Luckily, Brett Kavanaugh just led by example in his interview for one of the most important jobs in the nation. If these tactics are good enough for Brett, surely they’ll work for you. Even the President approved!

Just follow these seven simple steps to claim the job you’re already entitled to.

1. Hit your talking points, again and again.

Going into an interview, you won’t necessarily know what questions you’ll be asked — but frankly, that doesn’t matter. The most important thing you can do to prepare is to develop a set of talking points that you will bring up again and again and again. If you played varsity sports in high school, that is a very relevant thing to mention, especially if you’re now in your 50s. It’s also incredibly important to talk about your grades and how you had no help getting into an Ivy League institution. …


Image for post
Image for post

When Marc Benioff’s Behind the Cloud was published in the Fall of 2009, it was declared required reading for all 50 Box employees. Because I was new to the company and not yet acquainted with Aaron Levie’s insatiable appetite for business books, I complied. (I eventually retired from the “Levie Library” after slogging my way through High Output Management, and have adhered to a mostly-fiction diet ever since.)

Nearly a decade later, one mantra from that book sticks with me: “Tactics dictate strategy.” Benioff described how in its early days, Salesforce experimented with capitalizing on larger competitors’ marketing activities — something that began as a scrappy and creative tactic, but later became a marketing pillar. …


Image for post
Image for post

We met in a chat room. By we, I mean the three of us. Maura and I, huddled conspiratorially around her parents’ computer, clogging up the phone line. And Beau, presumably at his own family computer, if he was indeed the eighth grade boy he claimed to be, and not some middle-aged creep.

But Maura and I knew Beau was the real deal. You could see it in his unabashed use of exclamation points, the way he talked — er, typed — about all the sports he played. He was in our grade and attended a nearby school. Maura and I were instantly smitten. …


Image for post
Image for post

Whenever a technology company gears up to go public, I feel a wave of empathy tinged with nostalgia and a little PTSD. Nearly three years ago, Box, my then-employer, filed to go public. Ten grueling months later, we finally pulled it off. We dropped our S-1 at the start of a pretty brutal market correction and morphed overnight from a darling of enterprise software to a cautionary tale. The subsequent months were spent clawing our way back to a more nuanced place somewhere in between. It was the hardest and best thing I’ve ever been through professionally.

Of course, Snap is a very different beast, and its IPO is a very different (and much larger) IPO. To state the obvious: Box is an enterprise software company; Snap aspires to be the modern “camera company.” Box is an open and vocal product of the Valley; Snap prefers a more secretive existence in Venice. Perhaps most importantly, Box’s CEO has never been photographed by Vogue. …


Next week is my last at Box. After six amazing and crazy years, I’m joining Social Capital in December to run brand and talent. Since startup years are like dog years, I feel like I’ve spent many decades in the enterprise software industry. At the same time, I feel like I started yesterday.

I never imagined I’d work in enterprise software. But I’d gone to high school with the Box co-founders, and in 2009, one of them posted a community manager job listing on my Facebook page. “Know anyone?”

The timing was good. In 2007, Box had decided to ditch the flashier consumer market to focus on businesses, believing consumer cloud storage would be commoditized and building for enterprises offered more opportunity for differentiation. And after a long and bumpy tour of Sand Hill Road in 2007 and 2008 (hello economic downturn), Box finally raised a Series B to invest in putting that theory to work. By the time I joined in 2009, they were finding their footing selling to businesses, and things were starting to take off. …


Image for post
Image for post

When I joined Box to run PR in 2009, I was a baby. At 24, I had two years of work experience where my greatest achievement was avoiding any sort of media interaction. No small feat at a PR agency! Thanks to decent writing skills, I had carved out a safe, reporter-free corner where I could work on “messaging.”

Then I joined Box, and there were no corners. I had to do everything out in the open, with my successes and failures on full display because I was the only person doing my job. It was terrifying (and exciting). …

About

Ashley Mayer

All things communications. Beauty by way of venture capital and enterprise software.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store