v10 What I Learned Running a Startup for a Week
Last week, I unexpectedly got a crash course in what it really feels like to run a startup.
With our CEO on spring break, I was asked to step in and make final decisions across the business. I’m the Chief of Staff, so I’m used to operating across teams—but this was different. For one week, I lived the full founder life: from shaping go-to-market strategy and interviewing CFO candidates to reworking landing pages, writing agreements, and yes—restocking bathroom supplies.
I started early, ended late, and context-switched more than ever before. And by the end of the week, I walked away with one big realization:
Startups don’t run on titles or org charts. They run on people who wear the hats and fill the gaps.
A CFO candidate said it best…
During one of the CFO interviews I led, someone shared something that truly resonated:
“The best culture I’ve ever worked in felt like a collegiate environment. It didn’t matter your title, age, or background—everyone was working together on a class project, trying to find the fastest, smartest way to solve a problem. No silos. No politics. Just shared urgency and respect.”
He reminded me: early-stage CFOs aren’t just "finance leaders." They are a one-person department—expected to handle financial operations, cash flow, fundraising, accounting, payroll, and more. And when needed, they roll up their sleeves and help with business operations too. Titles don’t matter. Value creation does.
That’s the culture I want to build and protect.
What this week taught me about the founder journey
As someone who is on her Entrepreneurship journey, this past week's experience hit differently.
I’ve always understood, in theory, how much early-stage founders carry. But this past week gave me a front-row seat to the reality: founders are constantly throwing the ball and catching it too. One minute you're setting strategy, the next you’re restocking snacks, chasing down a draft contract, or unblocking someone in Slack.
And here’s the part that really stuck with me:
💡 Without people who proactively take weight off your plate, it’s not sustainable.
Not for the founder. Not for the business. That’s when I truly understood why early-stage CEOs need to be surrounded by two types of people—often rolled into one:
The Hat-Wearers:
They don’t just stick to their title. They flex, adapt, jump into new roles as the business evolves.
The Gap-Fillers:
They don’t wait to be told what to do. They look around, spot the white space, and take initiative.
These are the teammates who say, “I’ve got this” before you even ask. They free up the founder to focus on what only the founder can do: vision, direction, and high-leverage decisions.
Because when a founder is drowning in details, no one’s steering the ship. And the last thing any startup can afford… is a burned-out CEO stuck in the weeds. That’s why hiring people who wear multiple hats and fill the gaps isn’t just a hiring strategy—it’s a survival strategy.
👉 It’s foundational to building something that can actually scale.
The best people I’ve worked with had one thing in common: they filled the gaps and wore multiple hats.
Let me tell you about three of them.
First, our Executive Assistant.
While officially responsible for supporting the CEO and keeping the team running smoothly, she consistently goes above and beyond. She leads our benefits and payroll, contributes to marketing campaigns, and has even taken the lead in sales conversations with prospects. She’s one of those people who sees what needs to be done and does it—no job too small, no ego in the way.
Second, our QA analyst.
When we didn’t have a product manager or researcher in place, she stepped up to lead user interviews. She distilled real user pain points and feedback into themes, shared them with the engineering team, and helped improve the product direction—not because it was her job, but because the team needed it. That mindset didn’t just help the product. It helped her grow. Today, she’s formally transitioned into a product manager role—and even now, she continues to jump in wherever the business needs her most.
Third, our UX designer.
She was hired to focus on our app design. But when we needed help on packaging, marketing collateral, website visuals—even copywriting—she didn’t blink. She took it all on. She didn’t ask, “Is this my job?” She asked, “What does the business need right now?” In many ways, she’s been doing the work of two or three roles. She’s not driven by ego. She’s driven by mission.
These are the kind of people who move the needle in early-stage companies. They don’t hide behind job descriptions. They expand them.
This isn’t just a “us” thing. The best startups all do this.
At Stripe, early engineers were expected to write code and answer support tickets. Why? Because hearing directly from customers made them better builders—and because there wasn’t a “someone else” to pass it to. That culture of shared ownership helped Stripe scale with deep user empathy and low ego.
At Figma, before they had a dedicated community team, marketing filled the gap. They hosted events, managed user communities, and built relationships that helped turn early users into evangelists. That work laid the foundation for Figma’s famously engaged user base—and it didn’t come from a formal job description. It came from people stepping up.
At Superhuman, onboarding wasn’t just a CS function. Everyone—from the CEO to team leads—participated in 1:1 user onboarding. It was a high-touch, time-intensive process, but it gave the team unmatched insight into user behavior, objections, and value perception. It wasn’t “extra work”—it was essential to achieving product-market fit.
At Gusto, the ops team ran people strategy before a People team even existed. They led hiring, onboarding, culture-building, and internal comms—because someone had to. That scrappy, human-first approach didn’t just keep the company running. It helped create the culture Gusto is still known for today.
One Week, One Big Lesson
Startups don’t succeed because they hire the flashiest resumes or the most specialized roles. They succeed because they find the people who step up when it matters most.
People who:
- Wear whatever hat the moment requires
- Spot the white space and fill the gaps
- Default to action, not permission
- Care more about the mission than their job title
They’re the hat-wearers—versatile, curious, and unfazed by ambiguity.
They’re the gap-fillers—the ones who jump into the messy middle and get things unstuck.
That was my biggest lesson from stepping in as both Chief of Staff and CEO proxy for a week: ⚠️ I can’t throw the ball and catch it at the same time.
No matter how capable or committed you are, trying to own everything—strategy, execution, logistics, decisions—will eventually stretch you thin. The only way to lead well is to be surrounded by the right people—people who instinctively step in, step up, and take things off your plate before you even ask.
If you’re a founder or on the executive team:
Don’t just look for top talent. Look for the ones who wear the hats and fill the gaps.
That’s how you build something that lasts.
