Hidden gems – captive insurance offers job opportunities

We asked members of our FORTY Under 40 if they would recommend captive insurance as a career.

In a world where traditional career paths are being re-evaluated and emerging industries are vying for attention, one lesser known but highly rewarding sector is making a compelling case to young professionals: captive insurance. 

Once considered a niche area within the broader financial and insurance landscape, captive insurance is now stepping into the limelight – not just for its role in managing risk but also for the career opportunities it offers.

As part of our 2025 edition of FORTY Under 40, we asked a few of our chosen 40 captive insurance professionals how they started out. In some cases their introduction to captive insurance was almost accidental. 

Jennifer Allen, director of insurance and risk solutions at Ilitch Family Office, reflects on this common entry point: “When I graduated, a career in insurance wasn’t even on my radar, and I certainly had no idea what captive insurance was. Like many in the industry, I stumbled into it – and it has been one of the most rewarding discoveries of my career.”

Her words capture a recurring theme echoed across the industry – one of surprise, followed by deep satisfaction. And now, with the looming talent gap across the wider insurance sector, professionals such as Allen see captive insurance not only as a strategic career choice but also as a space brimming with opportunity.

“Captive insurance provides endless opportunities for growth and learning. It’s a dynamic space that is constantly evolving, allowing professionals to blend creativity with technical expertise,” Allen continued. “It’s never boring – the pace of change and innovation keeps things exciting.”

This excitement and dynamism resonate with other voices in the industry. Paige Bell, vice president and senior consultant for alternative risk solutions at Lockton, actively advocates for insurance careers among younger generations.

“I absolutely would recommend it to young people as a future career. I volunteer at my local high schools to speak on career day so more young people know that insurance is such a fantastic space. When they understand the global nature of our business and that it can include foreign travel, their eyes light up!”

For Bell, captive insurance is not just the domain of large corporations. “Captive insurance is increasingly becoming a solution, not just for the Fortune 500 companies, but for every company that understands risk and wants to better leverage their capital,” she told Captive International.

Indeed, the flexibility and strategic value of captives are a draw for companies and professionals alike. According to Meryl Bermond, business development manager at Descartes Underwriting, the industry is ideal for those seeking a fast-paced, intellectually engaging environment. “The captive insurance industry is dynamic and offers a unique combination of strategic thinking, risk management and innovation. For young professionals, it’s an exciting space that encourages creativity and offers opportunities for significant career growth.”

Bermond also highlights the industry's rapid evolution, particularly with the rise of advanced risk transfer solutions such as parametric insurance – emphasising that this is a space where forward-thinkers and innovators can truly thrive.

For Dylan Feringa, director at PNC Insurance, the answer to whether young professionals should consider a captive insurance career is unequivocal: “Yes, and yes again a thousand times over. I am convinced this industry remains an enigma in the best way.”

He points to the diversity and accessibility of the sector, noting that it is not oversaturated and offers real opportunities for early-career advancement – especially considering the expected retirement wave of industry veterans.

“The industry embraces young people and encourages active participation, which is not always the case in other industries.”

That inclusiveness is further reinforced by Caleb Hancock, director of client services – actuarial at GPW and Associates, who praises the collaborative nature of the industry.

“The sector is full of collaboration through different associations. Additionally, there are many great industry veterans providing mentorship to help young professionals develop.”

Hancock also highlights the ever-changing nature of captives as a major draw: "There will always be a new challenge on the horizon as businesses adapt to meet different needs."

Hartley Hartman, manager of captive business development at Risk Partners, calls the industry a "hidden gem" for a reason. “It’s a dynamic and evolving field that offers a unique blend of finance, risk management and problem-solving – making it an exciting option for young professionals looking for a career that is both intellectually stimulating and rewarding.”

Hartman notes the versatility of the sector, where a variety of backgrounds – from law and underwriting to actuarial science and business development – can find a fitting and fulfilling niche.

“Captives provide exposure to a wide range of industries, from healthcare to manufacturing to technology, which keeps the work fresh and engaging.”

He adds that the relatively niche nature of the field allows for faster career progression, with many professionals advancing quickly due to high demand and low supply of talent.

“For young professionals looking for a career that combines stability, innovation and long-term growth potential, captive insurance is an excellent choice."

Finally, Karen His, executive director of UC Captive Programmes, underscores the flexibility and customisation that captives offer – not only to businesses but also to individuals shaping their careers.

"There is an immense amount of career development opportunities in this industry... it truly is an industry where you can ‘make your career what you want it to be’.”

That ability to carve one’s own path in a high-growth, intellectually engaging and globally connected industry makes captive insurance an ideal career destination for young professionals ready to chart their course.

The captive insurance industry might not yet be a household name, but for those who find their way into it, it offers a rare combination: intellectual challenge, creative problem-solving, career progression and a strong sense of community. With a pressing need for new talent and an open door to diverse skill sets, it is a field ripe with opportunity – and one that young professionals would do well to explore.

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