Hiring with Conviction

Why Conviction Matters in Hiring

Jess Boss, the first talent hire at Neko Health, knows that great hiring isn’t about playing it safe. It’s about seeing potential others might miss, trusting your gut, and backing candidates who can shift the direction of a business. In this episode of the DexFactor Podcast, Jess shares the lessons she’s learned from hiring across engineering, R&D, medical, and corporate functions in one of Europe’s fastest-scaling health tech companies. Her insights are grounded in experience, shaped by curiosity, and delivered with clarity all the hallmarks of what Dex champions in modern recruitment.

Spotting a Game-Changer Before Others See It

One of Jess’s most memorable hires came during her time at Octopus Energy’s tech arm, Kraken Technologies. Tasked with finding the company’s first heads of product across four verticals, she knew it was a pivotal moment. Kraken had long been engineering-led, and these hires would help steer the company toward a more product-led future.

Enter Guy. His background in advanced robotics at Ocado and product experience in hardware sectors aligned beautifully on paper but Jess saw something more. His energy, confidence, and passion for product transformation stood out. "He was going to ruffle feathers but in the right way," Jess recalls. And that’s exactly what the business needed. Backed by her conviction, Guy was hired. He went on to play a critical role in reshaping how Kraken built product.

Good vs Great: The Surprise Factor

For Jess, the difference between a good hire and a great one is the surprise factor.

A good hire meets expectations. A great hire exceeds them in ways you didn’t even know to ask for. That surprise might be a trait, a skillset, or a perspective that shifts how the team thinks and operates. Jess points to a data science hire at Neko Health who had productionised a system remarkably close to what the company was building. It was unexpected, and it unlocked massive value.

Great hires bring qualities the business didn’t even realize it needed. And once they’re in, everyone knows it.

The Real Differentiator: Communication and Thinking Style

Across her career, Jess has seen a consistent thread among high performers: it’s not just what they know it’s how they think and communicate. The best hires don’t just hold knowledge; they share it. They align people. They elevate conversations.

One standout hire at Neko made such a strong impression through the interview process through thoughtful listening, clear articulation, and genuine curiosity that senior leaders now use them as a benchmark. “We want 20 more like that,” they’ve said.

Communication isn’t a soft skill. It’s a multiplier.

Learning from the Toughest Roles

Jess doesn’t shy away from challenge in fact, she embraces it. She cites her work hiring into the regulatory function at Neko Health as among the toughest of her career. Regulatory professionals, much like lawyers, are trained to identify and mitigate risk. At a high-growth, innovation-first company like Neko, that mindset can clash with the pace and ambiguity of daily operations.

Finding candidates who could uphold rigorous compliance while still enabling innovation required deep market mapping, mindset profiling, and creative outreach. Jess had to filter for those rare individuals who could say, “Here are the risks and here’s how we navigate them.”

These experiences have made her sharper. And more determined than ever to treat every role as an opportunity to stretch and grow.

What Makes a Mis-Hire and How to Prevent One

Early in her career, Jess faced a classic conundrum: two strong final candidates, very different profiles. One came from large corporate environments, with a history of stepping into strategic product roles. The other came from startups scrappy, adaptive, and ready for a step up.

The client chose the corporate profile. Jess had concerns. There were signs demanding a CPO title, pushing for detailed role definitions in a chaotic startup environment that this might not be the right fit. But she didn’t speak up strongly enough.

Twelve weeks later, the hire exited the business.

"That experience shaped how I recruit today," Jess says. "When you see amber flags, you have to raise them. Especially when you know your business and your candidate pool better than anyone else."

Advice for Candidates: Make Yourself Known

One of Jess’s top pieces of advice for job seekers: don’t just apply. Make yourself known.

Whether a company has open roles or not, reach out to the people who matter. Find the hiring managers, the recruiters, the heads of department. Send a message, show your passion, tell them why you care.

At Neko, for example, most roles aren’t even posted publicly. Headhunting is the norm. Candidates who make the effort to connect directly stand out immediately. And in competitive markets, that extra step often makes the difference.

Stand Out in the Interview Room

Once you’ve landed the interview, it’s about how you show up. At Neko, candidates are often asked: What’s something you’ve seen, read, or discussed recently that completely blew your mind?

It’s a question designed to find creative thinkers people who are curious about the world and passionate about the cutting edge. Jess encourages candidates to come prepared with something real, thoughtful, and personal. “We’re looking for people who are inspired and inspiring,” she says.

What Hiring Managers Need to Know

Jess’s message to hiring managers is clear: the more notice and clarity you give your talent team, the better the outcome.

Good hiring takes time. It takes partnership. It takes strategy. When hiring managers engage early, work collaboratively, and dedicate the time, the results speak for themselves. "We’re called talent partners for a reason," she says. "The best results come when we work in true partnership."

What Candidates Should Understand About Recruiters

Too often, candidates treat recruiters like gatekeepers instead of collaborators. Jess wants to change that.

We’re on your team, "We want to help you land your dream role. The more open, honest, and transparent you are with us, the better we can advocate for you.

Recruitment works best when it’s a partnership. When candidates and recruiters trust each other, share goals, and work together, the outcomes are better for everyone.

Hiring with Heart and Conviction

Jess Boss doesn’t just hire to fill seats she hires to shift the culture. To level up the business. To bring in thinkers, builders, and communicators who help companies become more of what they aspire to be.

Her episode is a powerful reminder that great hiring requires conviction, courage, and care. It’s not just about the job description. It’s about the mindset. The mission. The human.

And that’s what Dex is here to amplify talent stories that teach us how to hire with intention and build careers that matter.