From Golf to Growth

Ben Newsome has had three careers and each one has sharpened how he thinks about people, performance, and potential. A professional golfer turned recruiter, turned tech founder, and now Talent & Operating Partner at Octopus Ventures, Ben has developed a uniquely grounded view of what makes a great hire. It’s not just about capability. It’s about clarity, alignment, and whether someone makes the entire organisation better.

In this episode of the DexFactor Podcast, Ben shares lessons from his time hiring for high-growth companies like Monzo, Improbable, and across the Octopus Ventures portfolio. He dives deep into why great hiring starts long before a job description is written and how candidates and companies alike can get far more intentional about how they match.

The Hire That Changed the Game

One of Ben’s most memorable hires was for a Chief Product Officer at Receipt Bank (now Dext). It was a hard role not because the candidates were scarce, but because the founder had to hand over part of their identity.

“This was a moment where the CEO had to let go,” Ben explains. “And as anyone who’s worked in startups knows, that’s often the biggest challenge.”

Navigating the handoff required more than just running a process. It meant building trust, removing bias, and managing energy across the hiring squad. It took six months. But in the end, Ben helped the CEO land a senior leader who redefined how the business scaled.

That experience shaped how Ben works today: up-front alignment, total clarity on what great looks like, and the courage to push back when needed.

Good vs. Great: The Force Multiplier

Ben makes the distinction clearly: a good hire does the job. A great hire changes how the job is done and raises the bar for everyone around them.

“You see it in their impact on delivery, quality, even culture,” he says. “They’re not just filling a seat. They’re a force multiplier.”

In hiring, this is the gold standard. Great hires elevate team performance. They shape OKRs from the bottom up. They spark progress that ripples far beyond their remit.

The Secret to Speed? Alignment Upfront

At Improbable, Ben learned a lesson he still carries with him: if you do the upfront work, you can hire faster and better.

He remembers hiring a Principal Engineer at a time when that title didn’t even formally exist in the company. It was new territory. There were questions across the business about what it meant, where it sat, and what success looked like.

But Ben made the case. He got alignment. And when the process launched, they made the hire almost immediately.

“It was fast because we’d done the hard bit already,” he explains. “Alignment saves you months of pain later.”

The Hardest Hires Are the Ones You Don’t Prepare For

Asked about the most difficult hire of his career, Ben reflects on a lesson from agency days: the danger of unclear ownership.

That CPO hire at Dext? It nearly derailed multiple times. Without internal influence or infrastructure, Ben was building a process from the outside. Stakeholders weren’t aligned. The founder wasn’t ready to let go. Final stages kept collapsing.

What was missing? Preparation. “The hardest hires are the ones where no one agrees on what good looks like,” Ben says. “Or worse they think they do, but haven’t done the work to test it.”

Red Flags and Regrets: The Cost of Silence

Early in his career, Ben learned that staying quiet about red flags is never worth it.

He recalls a moment when two strong candidates were down to the wire: one highly qualified but misaligned with the company’s culture, the other a strong fit but less proven.

The client picked the first candidate.

Ben had doubts but didn’t speak up.

Within weeks, the hire had left.

“That shaped me,” he says. “Now, if I see a mismatch even if it’s unpopular I’ll raise it. That’s what I’m here for.”

Advice for Candidates: Know Your Why

Ben’s top advice to candidates? Understand what you want and be honest about it.

“It’s easy to chase the shiny offer, the brand name, the salary,” he says. “But fulfillment comes from fit. From being clear on your ‘why’.”

He encourages candidates to reflect deeply before making decisions. What matters to you? What does progress look like? What kind of environment do you thrive in?

And when you’ve done that work communicate it. “Hiring managers want to know what drives you. Don’t be afraid to show them.”

The Real Job of a Hiring Manager

Ben has strong views on what hiring managers often get wrong. “Hiring is one of the highest-leverage things a leader can do. But most underestimate the cost of doing it badly.”

Trying to own the process solo? That’s a mistake.

“You can’t run a great process and do your day job,” he says. “You need support. You need structure. And you need to partner with your talent team not just delegate to them.”

Ben’s advice: focus your energy on decision-making, not operations. Be present, not perfectionist. And treat your recruiter like your co-founder in the process.

Recruitment Is a Bow Tie, Not a Funnel

Ben offers a fresh analogy for thinking about recruitment not as a funnel, but as a bow tie.

The first half is acquisition: sourcing, qualifying, and closing.

The second half is expansion: onboarding, development, and long-term retention.

“The best hires aren’t just placed,” Ben explains. “They’re grown. Nurtured. Expanded into bar-raisers.”

It’s not just about who you hire it’s how you help them thrive.

What Candidates Often Miss

Ben urges candidates to look beyond surface-level brand appeal. Just because a company is big, doesn’t mean it’s right for you.

“Every company has a culture,” he says. “Some are bureaucratic. Some are political. Some are chaotic. Know yourself and choose accordingly.”

And don’t just wait for posted jobs. Get creative. Reach out. Build a personal pitch. The best opportunities often start from a cold message, not a live listing.

Final Thought: You Have More Options Than You Think

Ben wants people to know: there’s more opportunity out there than you realise.

Don’t rush. Don’t compromise. Do the work to know yourself. Then go after what actually fits.

“It’s your time,” he says. “It’s your energy. It’s your life. Don’t spend it somewhere that doesn’t make sense.”

Hiring as a Craft

Ben Newsome’s approach to hiring is deeply human, sharply strategic, and built on lived experience. Whether he's coaching a founder, supporting a portfolio company, or advising a candidate, his message is consistent: clarity, alignment, and care change everything.

Great hiring isn’t luck. It’s a craft. And it’s one of the most important levers a business has.

At Dex, we believe the same. That the right person, in the right role, at the right time can change everything.