Mentorship, culture and connection
In the second of two articles about Captive Review’s recent online panel of FORTY Under 40 judges, industry leaders outline the path for captive insurance’s next generation.
Talent development, mentorship and organisational culture are becoming central priorities for the captive insurance sector as it seeks to attract and retain the next generation of professionals.
In this, the second of two articles, we look at the recent panel discussion we held that featured seven judges from Captive Review’s FORTY Under 40 project, all industry leaders emphasised that structured mentorship, informal guidance and supportive workplace cultures will be essential to sustaining the industry’s future.
Moderated by Captive Review editor for Europe and the Rest of the World Marc Jones, the panel brought together senior figures including Anne Marie Towle, Sandy Bigglestone, Nate Reznicek, Grainne Richmond, Phil Giles, Renea Louie and Heather McClure.
Across the discussion, panellists repeatedly returned to a common theme: the captive sector’s complexity makes knowledge transfer between generations not just helpful, but essential.
Watch the full panel discussion below.
Mentorship as a cornerstone of the captive industry
For many of the panellists, mentorship is not simply a professional development tool but a defining feature of the industry’s culture. Phil Giles reflected on his own entry into the captive space more than two decades ago, noting that his career path was shaped by guidance from more experienced figures.
“I got into it probably about 25 years ago, shortly after I met a guy named Gary Osborne, who convinced me this is the direction I need to head,” Giles said. “The captive industry is a complex industry… it emphasises creativity and innovation, and a lot of times it takes a while to fully understand and comprehend this powerful ecosystem.”
Because captive insurance requires professionals to move beyond traditional risk transfer into more creative financing structures, Giles argued that mentorship programmes are crucial for developing new talent.
“Mentorship has to be an ongoing thing,” he said. “Being able to bring people into structured mentorship programmes that can help fully exemplify the amount of creativity and innovation you can exercise throughout this industry is critical.”
He added that early exposure to real-world client strategy is particularly valuable for younger professionals.
“Being able to instil early responsibility and exposure to these client strategy initiatives… where you can customise things down to a specific client’s needs… is essential.”
Building a “personal board of directors”
While mentorship programmes are important, several panellists stressed that individuals must also take ownership of their own development.
Anne Marie Towle highlighted the role of organisational culture and continuous education in supporting career growth. She noted that companies should demonstrate their commitment to development by funding professional qualifications, conferences and further study.
“Education here at Hylant is extremely important,” she said. “We encourage life-long learning, whether it’s seeking your ACI, conference attendance or other MBA programmes.”
Towle also introduced a concept she believes every professional should adopt: building a network of trusted advisers.
“You need to build your own personal board of directors,” she said. “You need people in your space, both internally and externally in the wider industry.” Such a network, she explained, provides guidance and perspective throughout a career.
“Everyone should have their own personal board of directors – people they rely on and go to for advice, challenges and to celebrate when things are going well.”
“We have to transfer everything that we know (to the next generation) so that they understand the ‘why’, not just the mechanics.”
Mentors, sponsors and connectors
From the Bermuda perspective, Grainne Richmond argued that mentorship works best when combined with other forms of support, including sponsorship and networking. “I think mentorship is extremely important,” Richmond said. “But I also think having a sponsor – someone who’s an advocate in your space – is just as valuable.”
Sponsors help ensure professionals are recognised and supported as they progress, she explained, while connectors help expand industry networks. “You do need different connectors… and that’s back to building your board of directors,” Richmond added.
She also highlighted the limits of relying solely on digital information in a complex industry such as captives. “Especially the upcoming generation, they feel everything is available either on ChatGPT or Google,” she said. “But there’s a lot in the captive space that is really through word of mouth – this is how we operate.”
For that reason, informal mentorship can often be just as effective as structured programmes. “I think some leaders get scared of mentorship, thinking it’s going to eat into their time,” Richmond said. “But there’s a lot to be said for informal mentorship – simply meeting someone for a coffee and talking through their concerns.”
Stretch assignments and growth opportunities
Sandy Bigglestone highlighted another important aspect of mentorship: giving emerging professionals the chance to expand beyond their immediate responsibilities.
“There’s certainly a need for mentorship for skill-building and understanding the technical environment,” she said. “But another important piece is helping people accelerate their growth through stretch assignments.”
These assignments allow employees to test their interests and abilities while expanding their expertise.
“My entire regulatory career was a stretch assignment,” Bigglestone noted. “I didn’t stay in one position very long… by the time 29 years had passed, I had worked in every position within the captive insurance division.”
Encouraging professionals to become “utility players” across multiple roles, she said, can strengthen both individuals and organisations.
Passing on institutional knowledge
For Renea Louie, mentorship also involves preserving the institutional knowledge that has shaped the captive sector over decades. Reflecting on the mentors who influenced her early career, Louie recalled how informal interactions helped build lasting relationships. “We didn’t realise they were mentoring us,” she said. “They were teaching us gently and kindly.”
Louie emphasised that leaders have a responsibility to share not just technical knowledge but the reasoning behind decisions. “We have to transfer our institutional knowledge,” she said. “We have to transfer everything that we know so that they understand the ‘why’, not just the mechanics.”
Creating opportunities for younger staff to observe decision-making processes can be particularly effective. “I let a lot of my employees sit in board meetings just to listen,” Louie explained. “The more they absorb and listen, the more the light bulbs go on.”
This kind of exposure builds confidence and encourages long-term commitment to the industry. “If they see we’re willing to invest in them, they’re willing to stay,” she added.
The role of industry organisations
Beyond individual companies, industry associations are also playing a growing role in mentorship initiatives.
Heather McClure pointed to programmes developed by the Self-Insurance Institute of America’s captive insurance arm, including mentorship initiatives connected to the Self-Insurance Institute of America Captive Insurance Committee and the Amplify Women programme.
These initiatives aim to pair emerging professionals with experienced leaders to strengthen representation and professional development within the industry. “For those who are seeking a formal mentorship pairing, that would be a great place to start,” McClure said.
She also highlighted the variety of career paths available within the captive sector. “It’s kind of like having a law degree,” she said. “You can decide you’re going to specialise in healthcare, construction or another sector.”
The ability to build a niche practice within the industry can be a powerful recruitment tool for younger professionals.
Preparing for technological change
Looking ahead, Nate Reznicek suggested that the next generation of leaders might experience a transformation comparable to the rise of the internet. “We’re at a time that’s transformationally similar to the change before and after the internet,” he said.
While technologies such as artificial intelligence may automate certain tasks, Reznicek believes they will also shift the focus towards experiential knowledge and strategic thinking. “I don’t think it’s all doom and gloom,” he said. “It provides opportunities to focus less on mechanical learning and more on the experiential things we’ve learned throughout our careers.”
However, he acknowledged that the interaction between emerging technologies and the highly regulated insurance environment remains uncertain. “I’m really interested to see how this flexibility and creativity overlays with the rigid regulatory framework we all have to live and work with,” he said.
A shared responsibility
Despite their varied perspectives, the panel reached a clear consensus: mentorship and culture will play a decisive role in the captive industry’s future.
Whether through structured programmes, informal guidance or industry initiatives, experienced professionals must actively share their knowledge and support those entering the field.
As Louie succinctly put it, the goal is to ensure the next generation understands both the mechanics and the purpose behind the industry’s practices. “We’re downloading all the AI in our brain to the next generation,” she said. “So their heart can carry it on for us.”
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