The Job Title Is Temporary. The Skills Are Not.

At 22, Nick Tooker thought a business economics degree would land him somewhere on Wall Street or helping shape strategy for a Fortune 500 company.

Instead, he found himself answering phones for a prominent NBA agent. Not the glamorous version, either.

"I was picking up dry cleaning, trying to convince airlines to hold planes because my boss was late, basically doing whatever needed to get done," Tooker says. "Think Lloyd from Entourage. Definitely not a titan of business."

It's not the opening scene most people picture for a future executive. Looking back, it's hard not to see why it mattered.

Today, Nick Tooker leads Partnerships and Corporate Development at Expensify, helping shape strategic partnerships while overseeing the company's quarterly earnings process. Corporate development focuses on strategic growth opportunities, partnerships, and business expansion initiatives, making it a natural fit for someone whose career has centered on relationship-building and storytelling. Between those two roles were five years negotiating sponsorships at Excel Sports and a leap into an early-stage startup that, at the time, looked like a questionable career decision to just about everyone except him.

From the outside, it reads like a career built on big pivots. Tooker doesn't really buy that. "The skills travel a lot further than whatever company name is on your LinkedIn profile," he says. The logos on the business card changed. The conversations never really did.

Different Rooms. Same Job.

During his time at Excel Sports, Tooker negotiated more than 100 sponsorship agreements. Sure, he learned how to negotiate contracts, but what stuck with him wasn't the mechanics of the deal. It was the people sitting across the table.

"When you do that many different deals, you kind of learn to see everything under the sun. You stop being surprised when things go south," he says.

There's something about repetition that speeds up perspective. After enough conversations, enough contracts and enough personalities, you stop trying to memorize the playbook and start recognizing patterns. Who listens. Who postures. Who wants to know you understand what matters to them.

He also learned something that still shapes the way he approaches partnerships today.

"Getting a sponsorship signed is really just the beginning. You have to actually make it work and make it valuable for both sides," Tooker says.

One mentor at Excel put it even more simply. "You're not selling a product to a company. You're selling to the person that's sitting right across from you."

It's the kind of advice that sounds obvious until you realize how rarely people actually do it.

Whether he's building a partnership, pitching investors or helping teams inside Expensify align around an idea, the work still starts in the same place: understand the human first. The rest tends to follow.

Betting on Skills, Not Certainty

When Tooker left Excel for a pre-seed startup in San Francisco, people had questions.

Mostly, why? "He thought I was joking," Tooker says, remembering the conversation with Excel's founder.

From the outside, it looked like he was trading stability for uncertainty. To Tooker, it looked like an education. "It was taking a risk on myself," he says. The startup lasted about a year. He still talks about it with surprising gratitude.

"It's like getting a real-life MBA. I probably learned more in that year than I had learned in the previous three." In twelve months, he touched fundraising, hiring, finance, operations and product. He wasn't becoming more specialized. He was becoming more versatile.

That mattered later.

When Expensify prepared to go public, Tooker built the company's investor relations function from the ground up. Most people wouldn't put investor relations and sports sponsorships in the same sentence. Tooker would. "It's extremely similar. You're just pitching a different product," he says.

Strip away the jargon and both jobs ask the same thing: Can you tell a story people believe? Can you earn enough trust so that they're willing to come along with you? Of course, believing in the story doesn't mean you aren't nervous while telling it.

"You have to be completely terrified... but not show that," Tooker says. His description of that feeling is one of the best in the conversation. "You’re like a duckling. Above the water, everything's calm. Below the water, you're completely freaking out." 

Today, his title is Head of Partnerships and Corporate Development, though he jokes it probably sounds more glamorous than it is. "I definitely am not shaking hands on a golf course. I don't golf."

Instead, his days are spent solving problems, connecting dots between teams, building relationships and, in his words, "influencing people to get things done that I don't have direct authority over."

Looking Back

One of the more interesting moments in the conversation came at the very end. We asked what he'd tell someone who worries they've chosen the wrong industry. He challenged the premise. "I don't think people pick the wrong industry. I think they pick the wrong seat," he says.

That distinction feels especially true when you look back across his own career. Sports became startups. Startups became public technology. The cities changed. The business cards changed. The responsibilities grew. The skills kept showing up. When Tooker talks about his career today, he spends surprisingly little time talking about the companies themselves.

Instead, he talks about what each one taught him. "Focus on what you're really good at. Sharpen those skills over worrying about what industry you're in." Looking back, it's easy to draw a straight line through his career. At the time, it probably felt anything but straight.

One opportunity led to another, each quietly preparing him for the next one in ways that only make sense with the benefit of hindsight. Job titles have a funny way of changing every few years. The skills tend to stick around much longer.