Insight

Why Staying Put Paid Off: 9 Years at One Startup (and What It Taught Me)

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There’s a lot of noise about moving fast and chasing quick exits, and staying put can feel like the bigger risk.

But sometimes, staying put is what unlocks the biggest growth.

When a business keeps evolving and the challenges stay interesting, sticking around can be the smartest move you make.

Dan Sherfield, CFO of Grind, isn’t someone who job-hops. He’s spent nearly a decade at Grind, starting out as Head of Finance and eventually becoming CFO. Over that time, he’s helped the business grow from four London cafes to a multi-channel coffee brand, launched during a pandemic, and stayed rooted in his belief that the right fit is worth sticking with.

Here, Dan reflects on what that journey has taught him: about loyalty, leadership, and how to build something that lasts.

From cafes to compostable pods

When Dan joined Grind in 2015, it was a small but growing high street brand with four cafes and startup energy. “We were a startup back then. It was great fun,” he says. There was no handyman, so when a coffee roaster wouldn’t fit through the garage door, Dan grabbed an angle grinder and took the door off himself.

By 2019, they’d grown to 11 sites, raised funding through CrowdCube, and invested in roasting and tinning equipment. But it was what happened next that changed everything.

In early 2020, Grind launched its online business, just before the pandemic hit. The timing was accidental but critical. Within weeks, their high street revenue dropped to zero. But online sales exploded. “We went to 10,000 a week and 20,000 a week and 30,000 a week,” Dan says.

That shift turned Grind from a cafe business into an omnichannel brand. Today, they split their revenue roughly into thirds: high street, online, and grocery/B2B. “It’s been a really exciting journey,” Dan says. “We’re trying to get better coffee that’s better for the planet into as many hands as we can.”

Always a startup person

Dan didn’t fall into startup life by accident. “I always knew I wanted to be in a small growing business,” he says. His parents ran small companies, and he spent his teenage years filing and doing expenses in his dad’s office. He studied maths and economics, trained at EY, but always had his eye on building something.

His first leap out of corporate life was to join a social enterprise, a factory in Haringey that produced clothes and trained local apprentices. It wasn’t a traditional next step for a Big Four accountant. But it set him up for Grind.

“I took a big pay cut. I made mistakes. But it was an amazing experience.”

“You need to believe in what you’re building. And I really believe in what we’re building. That’s been really important to anyone in their career but particularly as you’re working towards these businesses that are trying to build something.” – Dan Sherfield, CFO of Grind

Problem solving and purpose

Ask Dan what keeps him engaged, and the answer is simple: solving problems. “I’m not great with a blank canvas. But give me something to fix, and I’m in,” he says.

At Grind, that’s meant everything from figuring out how to build a finance function from scratch to navigating the shift to DTC. His role has evolved alongside the business. Early on, he was FP&A, commercial finance, investor relations, and everything else. Now, it’s much more about leadership.

“You go from being in the weeds to thinking about strategy, structure, and how you lead a team,” he explains. “That’s been the most rewarding thing I’ve done.”

He’s also proud to work for a brand with purpose. Grind is a certified B Corp, with a clear sustainability agenda and a commitment to ethical sourcing. “We’re not perfect. But we’re trying to be better every day.”

When you find the right fit, stay

Nine years is a long time in startup land. But for Dan, the fit was right, and it still is. “I’m proud of the product. I’m proud of the brand. I love the challenge,” he says.

It helps that his relationship with Grind’s CEO is strong. “We view the world in the same way. We complement each other’s skill sets. That relationship is pivotal.”

He’s quick to acknowledge that luck played a part. Right place, right time. But it’s also about knowing when it’s working. “I’ve lucked out. But also, I know what I want from a business, and this gives me that.”

Family first, always

Dan’s had three kids during his time at Grind. And he’s made it clear to everyone he works with that being a dad comes first.

“Everyone in the business knows that I’m walking out the door at five. I don’t sneak out. I say it. And if I need to log on later, I will. But I’m going home.”

That boundary-setting isn’t just personal, it’s cultural. “We’ve got working parents in the business who are encouraged to do the same. Clear goals, deadlines, and trust. That’s what matters.”

Her own leadership style blends optimism with accountability. “I take my work very seriously. I don’t take myself very seriously. But I will show my teeth if I need to.”

Better decisions, not just better numbers 

Dan’s view of finance is grounded in one principle: the job is to help the business make better decisions.

“The purpose of finance is to deliver accurate and timely information that gives visibility to make better decisions,” he says. That means prioritising what matters, even when there’s a lot going on.

“You walk into a startup and everything’s a mess. You have to ask: what are the most important decisions we need to make? Focus there. The rest can wait.”

That mindset has shaped how he leads. “You don’t need to know everything. You need to prioritise. Communicate. And then go home.”

“The most important thing about a CFO is you’re a leader. First and foremost, you’re a leader of your team. And you can only be that leader and a good leader if you’ve got a great team beneath you.” – Dan Sherfield, CFO of Grind

Being a CFO is about leadership

Dan remembers hearing a CFO from Deliveroo say he wasn’t an accountant. At the time, it shocked him. But now he gets it.

“The most important thing about being a CFO is being a leader,” he says. That doesn’t mean the numbers don’t matter. But you can build the team around you. “If you’re not an accountant, make sure you have a strong FC.”

He sees his job as connecting the dots: strategy, operations, numbers. “You don’t need to be perfect at all of it. But you do need to make good decisions. That’s the point.”

Let AI do the heavy lifting

Grind is already trialling AI tools across the business, and Dan’s finance team is no exception.

“We’re putting software in place that can write my board report for me,” he says. The opportunity is huge. Less time building numbers, more time analysing them.

“AI can’t understand context. But it can free you up to spend more time on the things that matter.”

What staying put can teach you

Dan never planned to stay at one startup for nearly a decade. But the journey has given him more than just a CV of promotions. It’s taught him what matters.

“I’m proud of my team. I’m proud of what we’ve built. And I’m proud that we’re always trying to get better.”

Advice for CFOs thinking long-term

  • Lead first, don’t just report the numbers.
  • Prioritise what matters and let go of the rest.
  • Help the business make smarter decisions, not just cleaner data.
  • You don’t need all the answers, just the ability to focus.
  • Set the tone for balance and back it up with action.
  • Let AI handle the heavy lifting so you can do the high-value thinking.
  • If the mission fits, stick with it, growth comes in many forms.
  • Keep raising the bar. A little better, every day.

Listen to the episode of the STOIX Podcast

To hear Dan Sherfield’s full conversation, watch the complete podcast episode here:

To connect with Dan or explore more of her experience and insights, head over to Dan’s LinkedIn profile.