FORTY Under 40: Mark Aylward
Mark Aylward, vice president, Global Captive Management.
Aylward, originally from Durban, South Africa, started his academic journey at the University of Cape Town, where he earned a bachelor’s degree in economics and finance, followed by a postgraduate diploma in management, then a postgraduate diploma in accounting through the University of South Africa.
After finishing his three-year training contract with Mazars in Johannesburg and passing both board exams, he qualified as a chartered accountant in 2014. He is currently a member of both the South African Institute of Chartered Accountants and the Cayman Islands Institute of Professional Accountants.
Not long after qualifying, he moved to the Cayman Islands and joined KPMG’s insurance and enterprises division. He spent two busy seasons learning the ins and outs of the captive insurance industry, but quickly realised auditing wasn’t really for him. So, in 2016, he jumped into captive management and joined Global Captive Management (GCM) as an account executive.
Fast forward to 2026, and he’s now a vice president, leading internal and client teams and working with a wide range of captives.
Looking back at your journey over the past year, what accomplishment are you most proud of, and how has becoming a FORTY Under 40 finalist influenced your perspective on that achievement?
I’ve been most proud of the success within my team and GCM as a whole – seeing my direct reports earn promotions, grow in confidence and really level up has been a major highlight. My VP promotion (even if it was just over a year ago!) also still feels like an important milestone. It all came during a great year for GCM, where we made real progress on culture and employee wellbeing, something I’m passionate about. Being named a FORTY Under 40 finalist made me pause and appreciate all of it.
What key challenge did you face in your work this year? How did you overcome it and what did it teach you about leadership at this stage of your career?
One this year was balancing a growing workload and responsibilities while still supporting my team the way they deserved. The more responsibility I took on, the easier it was to default to “I’ll handle it”. Learning to delegate properly – and actually trusting the team to run with things – was tougher than I expected.
Along the way, I learned a lot from other leaders and even newer employees, each bringing their own perspectives. I also had to get better at navigating different personalities and viewpoints. It reminded me that leadership is an ongoing process – and I’ve still got plenty to learn.
“Learning to delegate properly – and actually trusting the team to run with things – was tougher than I expected.”
In what ways have you tried to push innovation or rethink traditional approaches within your sector, and what impact has that had on your team or organisation?
This year I’ve really tried to push innovation by challenging some of the old “this is just how we do it” processes. As the team lead on our standardisation and automation committee, I’ve been helping take a deep dive into everything we do – figuring out what can be streamlined, where tech can help and what new tools (including AI) might keep us ahead of the game.
The biggest impact so far has been on mindset. It’s getting our team to think more creatively, buy into new ways of working and feel comfortable challenging the usual approach. It also requires strong leadership support, because some of these improvements take serious time and capital to get right. But when planned well, the payoff can be tremendous for both the team and the organisation.
How do you see your role evolving over the next three to five years, and what initiatives are you most excited to pursue as you continue to grow professionally?
In the medium term, I see my role evolving into one even more focused on growing people and driving innovation at GCM. I’m really excited about developing the next group of leaders – helping them build confidence, take ownership and shape the future of the company in their own way.
At the same time, with technology and AI becoming more and more relevant in our industry, I want to keep pushing for smarter, more modern ways of working. There’s a huge opportunity to rethink how we operate, stay ahead of the curve and make the business stronger and more resilient for the long term.
Many of the FORTY Under 40 winners are recognised for both business success and broader impact – how do you balance professional excellence with contributions to your community or industry landscape?
For me, balancing professional excellence with broader impact really comes down to investing in my team. Mentoring people, helping them grow and creating a culture where everyone feels included and supported is something I make a priority. I try to be available, share what I’ve learned, and make sure the environment encourages wellness, openness and confidence.
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