Between mid 2025 and 2026 I managed four consecutive retained claims leadership searches essentially back to back. Two for a global (re)insurer and two for one of the world’s largest and most respected (re)insurance groups in the London/Lloyd’s/Global market. All four were leadership remits and all four were complex. All four successfully concluded as of June 2026.
I want to share what that run of mandates taught me, why these searches demanded a specialist retained approach and what it should tell claims leaders and (re)insurance businesses about the current state of this talent market.
The Market Context: Why These Roles Can Be So Hard to Fill
Senior claims leadership in the global (re)insurance market is one of the most competitive and undersupplied talent pools I’ve worked in across my career. The individuals who can genuinely lead at that level, technically authoritative across complex, multi-line portfolios, capable of operating across jurisdictions and with the strategic and people leadership to match, represent a tiny fraction of the overall market. Most of them are not on LinkedIn refreshing their inbox. They are not responding to job boards. They are often not thinking about a move at all.
That is precisely why retained search exists and it is precisely why the four searches I’m going to describe each required the same thing: deep market knowledge, genuine relationships, a global lens and the patience & rigour to do the process properly.
Search One: Global (Re)Insurance Claims Leadership, Bermuda
The first call came from a global (re)insurer building out their Bermuda operation. They needed someone to establish a claims function from the ground up. Not to step into an existing team. Not to manage a process someone else had designed but to build it.
The role demanded technical capability across a genuinely broad commercial claims portfolio across multiple global reinsurance lines. A profile that immediately ruled out generalists.
My approach was straightforward in concept, harder in execution. I expanded the search entirely looking across London, Bermuda and the broader international market for senior professionals with the credentials and the appetite to relocate. I conducted a comprehensive market mapping exercise: not a database trawl, but direct, discreet outreach to carefully identified individuals.
Eleven suitable candidates were initially vetted and considered from the research. Seven progressed to 1st stage formal interviews, a small select group of standout individuals then progressed to the further stages. An offer was accepted 12 weeks after engagement with the successful individual due to start their new position in Bermuda later in 2026.
The successful candidate was based in London at the time of appointment, a Claims leader at a respected (re)insurer with extensive exposure to complex reinsurance across multiple lines and geographies. What set them apart wasn’t just their technical breadth. It was the combination of that breadth with genuine operational and strategic build experience: they had developed and ran claims functions, not simply worked within them. That combination, at that level, is genuinely rare.
Bermuda is an exceptional market, but it can be naturally constrained by the size of its senior claims talent pool, with demand for experienced leaders consistently high. Many of the strongest on-island professionals are already well established in significant roles, making external search an important way to broaden the available talent pool rather than replace it. By partnering with Claims Recruitment Services, the client was able to expand the search to a global pool of proven claims leaders, ultimately delivering the best possible outcome while ensuring the successful candidate was selected purely on merit and suitability for the mandate.
Search Two: Cyber Claims Leadership London
The second mandate came from a leading (Re)Insurer & Lloyd’s Syndicate. They needed a new senior leadership appointment to lead a cyber claims function that had grown substantially in size, complexity and global reach.
This is a class of business where the technical landscape is evolving at pace. The person needed to lead a globally distributed team, navigate an increasingly sophisticated and active claims environment and do so with the commercial and strategic awareness to sit credibly on a Claims Leadership Team at group level.
The search required candidates with deep cyber claims expertise, not general liability, FL or technology experience dressed up as cyber, alongside proven leadership capability and the interpersonal range to manage internal and external stakeholders across multiple time zones and jurisdictions.
Cyber claims leadership talent of this calibre is not plentiful in the London market. There are talented individuals working in cyber claims, but individuals who have already operated at a true global leadership level, with the breadth and the gravitas to match, are a much smaller group.
The search was completed successfully, with a high-calibre appointment confirmed and already started in their new position.
Search Three: Claims Leadership & Global Portfolio Head London
The third and fourth searches were both for one of the world’s largest & leading (Re)Insurance groups in the world. Both mandates were genuinely different in scope, which illustrates something important: retained claims search at this level is not a repeatable template exercise. Every brief has its own complexity.
This was a newly created global claims leadership role. This person would sit within the Group Claims Leadership Team, overseeing a complex (re)insurance portfolio involving highly complex, high-value, often CAT-linked losses across global client bases.
What made this search particularly demanding was the nature of the mandate. This was not a Head of Claims role in the conventional sense, it was a claims leader with an upwards and outwards lens: someone who could gather intelligence, identify patterns, connect dots across the group’s global footprint and drive coordination where historically the regional teams had operated more independently. The client described it as a Head of Claims role “plus” a description that immediately signals how narrow the pool of truly qualified candidates is.
This search was successfully concluded, with the appointed candidate due to start later in 2026.
Search Four: Global Claims Leadership (Re)Insurance
The fourth mandate, from the same reinsurance group, was a different kind of complexity. This was a senior strategic & operational leadership role with accountability for managing and developing all regional claims teams globally, alongside oversight of the group’s outwards reinsurance recovery function.
The person needed to provide consistency of philosophy and approach across London, Bermuda, US and Europe, reserving practices, file handling standards, performance reporting, regulatory compliance, succession planning and resource development. In short, they needed to provide the operational glue that holds a globally distributed claims function together.
Candidates of this calibre, people who have genuinely led across multi-jurisdictional claims operations at senior level are rare and again, rarely looking. Finding them requires the same disciplined approach: targeted global market mapping, direct and confidential outreach and rigorous vetting for both technical credentials and genuine leadership depth.
The search was completed successfully in June 2026 with announcements to follow.
What Running Four Consecutive Retainers Teaches You
Four mandates of this nature, end to end, reinforced several things I already believed and taught me a few things I hadn’t fully articulated before.
The talent pool is smaller than most clients expect. At senior claims leadership level in (re)insurance, the number of individuals who genuinely have the technical depth, the leadership credentials and the build or transformation experience to succeed in the most demanding roles is very small. You cannot find them by posting a job advertisement. You find them by knowing the market.
Clients who brief well get better outcomes. In all four of these mandates, the clients were thorough, thoughtful and engaged. They gave me the access, the context and the honest assessment of what they needed that made it possible to assess candidates at depth. That partnership matters enormously.
Pace and rigour are not in conflict. The searches have been closed within timeframes relative to the complexity of the brief. Retained search does not have to be slow or quick. It has to be structured, disciplined and managed closely. Done well, it can move fast because there is no duplication, no noise and no confusion about who is leading the process but breathing room on both sides for reflection, review and debriefing is imperative.
The right candidate is almost never actively looking. In each of these four searches, the successful candidate was approached, not found. They were in good roles, respected in their markets and not thinking about a move. Part of my job and one of the things I believe I do well is identifying those individuals, understanding what might genuinely motivate them to consider something different and presenting opportunities in a way that makes the conversation worth having.
Why This Matters for Claims Leaders and (Re)Insurance Businesses
If you lead a claims function or lead a business that depends on getting its claims leadership right what I’ve described above hopefully resonates.
The market is not getting easier. Claim complexity is increasing across every class. Regulatory and stakeholder expectations are rising. The people who can genuinely lead at the highest level are in short supply and high demand. Getting it wrong at leadership level is expensive. Getting it right is foundational.
Retained search, done properly by a specialist who actually knows this market, is the most reliable way to access the best of this talent. Not the only way but the most reliable one, given I’ve developed a bespoke in-house search methodology specifically with claims leadership in mind, myself and Claims Recruitment Services should at the very least be on your considering list.
I have spent over a decade in this market. My entire focus is on claims. I know the talent, I have the relationships and I understand what great looks like at every level of the function from adjuster through to Group Head.
I’m excited to now be moving ahead with our 5th Claims Leadership mandate for 2025 & 2026 and am looking forward to the challenge & journey over the coming weeks this August.
I’m excited to now be moving ahead with our 5th Claims Leadership mandate for 2025 & 2026 and am looking forward to the challenge & journey over the coming weeks this August.
If You’re Building or Strengthening a Claims Leadership Team
I’d be delighted to talk.
Whether you’re looking to make a single, senior appointment or planning a broader restructuring of your claims leadership or claims team, I operate as a genuine strategic partner throughout the process not just a supplier. The wider team at Claims Recruitment Services has the capability to identify, approach, acquire and retain the best and leading claims professionals at entry level all the way up to Group Head/CCO/COO. Get in touch for a confidential chat today.
Jamie Thomson Managing Director, Claims Recruitment Services 📞 +44 7387 351 811 ✉️ jamie.thomson@claimsrecruitment.co.uk 🔗 Connect with me on LinkedIn 🌐 claimsrecruitment.co.uk
Claims Recruitment Services is one of the only claims-specialist recruitment consultancies in the UK. We operate across the Lloyd’s, London & international (re)insurance markets, placing claims professionals at every level from emerging talent to leadership. For more information please feel free to contact me, visit www.claimsrecruitment.co.uk
By Jamie Thomson, Managing Director, Claims Recruitment Services
