When people hear me say that I’m the Executive Assistant to a unicorn startup CEO, the reactions are usually one of two things: “Wow, that must be glamorous!” or “So… you do scheduling?” I usually just smile and nod because trying to explain what I actually do feels like trying to explain quantum physics during a coffee break.
But here’s the truth: being the EA at this level is more like a high-stakes game of 4D chess, less like the “The Devil Wears Prada”. It’s always on fire; there is something to do every day and every time. I joined this company back when we were a scrappy series. A team squeezed into a WeWork. The CEO was 28. Brilliant. Impatient. Running on caffeine, cortisol, and conviction. I was supposed to “keep things on track.” I thought that meant booking meetings and organizing Notion boards. But that quickly turned into managing fundraising, cleaning up investors’ decks, screening people who wanted to meet the CEO for just “15 minutes”, and eventually becoming the unofficial chief of staff.
Now we’re a unicorn, and my job has evolved into something that feels like a hybrid of ops lead, gatekeeper, therapist, and sometimes, babysitter.
My day usually starts around 6 am, usually a Slack message from the CEO that says something cryptic like, ” Need to talk to JP before noon”(no context, of course). I figure out what J.P. means, what he might want to talk about, and whether we have his number, how to fit into between an already packed day of board calls, product reviews and some ridiculous podcast interview someone committed him to without asking.
It’s part detective work, part diplomacy, part fire-fighting. I once had to re-route a private jet due to a last-minute conference change and simultaneously find a last-minute gift for a partner’s wedding, all while pretending it was just another Tuesday.
But it’s not all chaos. There’s strategy, too. I sit in on most leadership meetings. I get copied on almost every email that matters. I know what keeps the CEO up at night. I know when he’s avoiding something. I know when the leadership team is aligned and when the wheels are about to come off. And when it gets political (it always does), I stay neutral, invisible, and useful.
Being an EA at this level means influencing without ego. You have to be smart but not threatening, confident but discreet. You don’t just manage time; you protect energy, reputation, and momentum. If the CEO is a race car, I’m the pit crew, keeping it moving at top speed without blowing up.
People ask me how long I’ll keep doing this. Honestly? I don’t know. It’s exhausting. But it’s also the best MBA I ever paid for. I’ve seen companies rise, implode, and rise again. I’ve seen the real Silicon Valley, not the TechCrunch version, but the messy, brilliant, behind-the-scenes hustle that builds billion-dollar companies.
And I’ve had a front-row seat to all of it.