Finding the next generation of leaders
In the first of two articles, Captive Review summarises the initial findings of a recent panel consisting of the judges for this year’s FORTY Under 40.
The captive insurance sector is entering a period of significant transition. As experienced professionals approach retirement and new technologies reshape working practices, attracting and retaining talent has become one of the industry’s most pressing priorities.
That theme was central to a recent panel discussion hosted by Captive Review, where several judges from the publication’s FORTY Under 40 awards programme reflected on what defines emerging talent and what the industry must do to build the next generation of leaders.
Moderated by editor Marc Jones, the panel featured senior figures from across the captive ecosystem, including Anne Marie Towle, chief executive of Hylant Consulting; Sandy Bigglestone, managing director and chief governance, regulatory and compliance officer at Strategic Risk Solutions (SRS) Titanium; Nate Reznicek, president of Captives Insure; Grainne Richmond, EVP and head of captives at Aon Insurance Managers (Bermuda); Phil Giles, chief growth officer for accident and health at Skyward Specialty; Renea Louie, chief executive of Sotera Global Management and Heather McClure, managing partner and general counsel at Helio Risk.
Together they explored the recruitment challenges facing the sector, the role of mentorship and the growing influence of artificial intelligence.
Watch the full panel discussion below.
A niche industry searching for talent
Opening the discussion, Jones noted that the FORTY Under 40 list highlights “some of the most dynamic, innovative and forward-thinking professionals shaping the captive insurance industry”. However, identifying those rising stars also underscores the importance of sustaining a robust talent pipeline.
Louie described the sector’s hiring challenge as a “great captive industry paradox”. While captives are now more widely recognised than in previous decades, there is still no structured path into the profession.
“When I was recruited into this industry, it was purely by accident that I fell in here,” she said. “There is no structured campus recruiting track. There’s no big four feeder programme. No one really rolls out of bed at 18 and says, ‘I’m going to be in the captive industry and manage a captive.’”
Instead, firms often recruit from adjacent industries such as insurance, banking and finance. For Louie, the key attribute is not technical expertise but analytical ability.
“We’re looking for critical, analytical thinkers; everything else is built from within,” she explained.
Towle echoed this view, highlighting the captive sector’s position as a specialised corner of the broader insurance market.
“Captives are a very small insurance industry that is very niche within the wider market,” she said. “Being able to spread the word and give visibility to the different types of careers –whether it’s captive management, legal, actuarial or regulatory – is essential.”
She stressed that knowledge transfer and mentoring will become increasingly important as senior leaders approach retirement.
“Many of us are probably not more than 10 to 15 years away from retirement,” Towle noted. “When many of us start to step aside, that will create a gap, and it’s important we prepare the next generation.”
“(Candidates)...should be interviewing us. The really good ones have their choice right now.”
Competition for skills intensifies
Several panellists agreed that competition for talent has intensified across the industry.
Phil Giles pointed to demographic pressures as a major factor. “The projected retirement of nearly half of the captive industry over the next 10 years has created an incredible need for finding and developing good, solid young talent,” he said.
This demand extends across multiple disciplines, including underwriting, actuarial science and captive management.
“With that comes competition for good emerging and specialised talent across all segments of the industry,” Giles added.
Heather McClure highlighted the operational impact of talent shortages. Even when firms succeed in winning new business, they must ensure they have the people to deliver on their promises. “If we’re bringing tons of business in but don’t have the professionals to staff that work, we’re in trouble,” she said.
The result is a recruitment environment in which candidates increasingly hold the advantage. According to McClure, young professionals often approach interviews with detailed questions about career progression, mentorship and workplace culture. “They should be interviewing us,” she said. “The really good ones have their choice right now.”
Culture, mentorship and career pathways
The panel repeatedly emphasised that recruitment is only part of the challenge. Retention depends on providing meaningful career opportunities and a supportive workplace culture.
McClure noted that candidates frequently ask about mentoring programmes, conference attendance and long-term career plans.
“They want to know what that pathway looks like,” she said. “What does a three-to-five-year plan look like?”
Giles agreed that organisations must demonstrate a clear commitment to professional development.
“Once you get them, you have to continually develop them,” he said. “Being able to outline not only immediate skill development but also ongoing progression is very important.”
For Sandy Bigglestone, transparency around career paths is essential for sustaining the industry’s growth.
“The captive industry thrives on expertise, innovation and collaboration,” she said. “We need to ensure those career paths are transparent so the next generation can really make their mark.”
She also stressed the value of industry outreach and education.
“If everyone connected with a college student in an advisory capacity, it could have a tremendous impact on talent acquisition,” Bigglestone suggested.
Bermuda’s perspective on recruitment
From a Bermuda standpoint, Grainne Richmond highlighted additional workforce dynamics.
As an international insurance hub, the island relies heavily on a transient workforce operating on limited-term work permits.
“Bermuda will always be a jurisdiction with a very transient employee workforce,” Richmond explained.
However, local organisations and government initiatives are working to increase opportunities for Bermudian professionals within the industry.
Despite technological advances, Richmond believes people remain central to captive management.
“No matter what AI or technology you bring in, it’s that employee and personal connection with clients that is key to our success,” she said.
Her ultimate objective as a leader, she added, is simple: “My first goal is client retention, but my ultimate aim is employee retention, because that ensures client retention.”
Artificial intelligence enters the conversation
Artificial intelligence emerged as a recurring theme during the discussion, particularly in relation to recruitment and changing job roles.
Reznicek observed that AI-driven automation is already transforming certain entry level tasks.
“Agentic workflows happening behind the scenes are reducing the need for entry level roles that used to move data from place to place,” he explained.
This shift might require companies to rethink their hiring strategies.
“Instead of focusing on people pushing papers around, we’re looking for individuals who can analyse and interpret what the data means,” he said.
However, panellists were unanimous that AI will not replace the human expertise at the heart of the captive sector.
Towle argued that technology should complement rather than replace professional judgment. “AI can be very powerful,” she said. “But you still need the intellectual capital and interpretation. We all say, ‘You’ve seen one captive, you’ve seen one captive.’”
Louie agreed, stressing the importance of independent thinking.
“We need people who can think for themselves,” she said. “Don’t fake it until you make it. In this industry you have to do the work and develop those critical thinking skills.”
Building the next generation
Despite the challenges, the panel expressed optimism about the future of the captive industry and the calibre of emerging professionals.
Louie praised the quality of applicants to the FORTY Under 40 programme.
“The applicants were absolutely incredible this year,” she said. “We have a very exciting future with the leadership coming up in the next generation.”
Ultimately, the discussion reinforced a central message: the success of the captive sector will depend on its ability to attract inquiring, analytical minds and nurture them through mentorship, training and meaningful career opportunities.
As Bigglestone concluded, “Captives are a people-oriented industry. If we invest intentionally in education, outreach and talent development, we can ensure a strong pipeline for the future.”
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