Recruitment Kept Calling - Jon's Journey at Pioneer Search

They say every great career starts somewhere, some with a degree, others with a lucky break, and in Jon Rogers’ case, with a knack for selling and a passion for connecting with people.

From Graduate hiring to high-level Search

Jon’s first experience in recruitment was very different from where he is today. He started his career placing graduates into sales role, an environment where speed and volume were key. The focus was on high-energy sales, assessing potential quickly, and matching raw talent with fast-moving opportunities.

While it built a strong foundation in resilience and relationship-building, Jon soon found himself drawn to a different challenge - selling high-value event sponsorships in the conference industry. This shift into corporate sales sharpened his ability to engage with senior executives, understand business drivers, and negotiate complex deals.

But despite his success in event sales, recruitment kept calling.

Building a successful Data recruitment function

In November 2020, mid-pandemic and during the UK’s second lockdown, Jon took the leap back into Recruitment, joining Pioneer Search to focus exclusively on Data & Analytics. With no networking events or industry mixers to rely on, Jon had to build his desk remotely, proving that great recruiters don’t just work the room, they create opportunities no matter the circumstances.

Despite the unconventional start, Jon quickly immersed himself in the London Market insurance sector, diving into conversations about Blueprint II and the Future at Lloyd’s. His ability to navigate and translate complex industry trends helped Pioneer Search expand its expertise and make a name for itself in the Data & Analytics space.

Climbing the ranks: Director of Executive Search

Fast forward to 2025, and Jon’s hard work has paid off. His promotion to Director of Executive Search is the result of four years of relentless networking, industry insight, and an innate ability to connect top talent with the right opportunities. From underwriting transformation to strategic hiring, Jon has become a go-to advisor for specialty insurance firms looking to level up their leadership teams.

Reflecting on his journey, Jon shares:
"Having spent the last four years building a deep network of (re)insurance professionals, stepping into this role feels like a natural evolution. The past few years have been incredibly rewarding, but the road ahead is even more exciting. I’m looking forward to guiding organisations through their next phase of transformation."

Thinking of a career in Recruitment? 

Here’s Jon’s advice:

"Enjoy the pursuit of excellence. We care about what we do, so it’s important you do too. We support each other in every aspect, so as a team, we have the ability to improve every day."

Looking for a specialist tech recruiter—or maybe even your next career move?

If you're looking for expert support in securing executive-level IT talent, particularly within the Specialty Insurance sector, Jon is the person to speak to. With his extensive network and deep understanding of the industry, Jon is well-equipped to connect you with top-tier candidates who will drive transformation and success within your organisation.

Alternatively, if you’re a recruiter looking for a workplace that offers genuine support, development, and career progression, Pioneer Search is expanding!

Get in touch with India today for a confidential chat about joining our growing team.