Caymanian Career Success Stories is a series of profile interviews with financial services professionals, highlighting Caymanian talent and the diverse career opportunities available across the industry. The series features professionals at different stages of their careers, from early-career professionals and the next generation of future leaders to experienced senior leaders across a range of sectors.
Each interviewee shares real and relatable experiences, offering our Caymanian community practical insights into how to enter the financial services industry, develop their careers and progress towards leadership roles. The series begins by exploring careers in the trusts and private client sector, followed by profiles from the reinsurance and captive insurance sectors.
The series was developed by Brittany MacVicar, Associate Director for Insurance, Reinsurance and Trusts Sectors at Cayman Finance. MacVicar explains the idea behind the interviews:
“As a proud Caymanian who has worked in financial services for over a decade, I know the talent is here. One of the best ways we can encourage more Caymanians to see themselves in this industry is by highlighting people they know and can relate to who are already building successful careers within it.”
Jackson Messer, Appleby
Jackson Messer is an Associate in Appleby’s Private Client and Trusts team. Born and raised in Grand Cayman, he attended CIS before completing his high school education in Canada. He went on to earn a Bachelor of Commerce in International Business at Dalhousie University in Halifax, Canada.
Jackson then studied law at City University of London, completing the two-year accelerated LLB programme followed by the Legal Practice Course. He trained in Cayman with Appleby as an Appleby scholarship student, and has remained with the firm’s Private Client and Trusts team.
Q: Could you tell us about your current role in the industry?
A: I’m currently an Associate in the Private Client and Trusts team at Appleby, working primarily as a non-contentious lawyer. Day to day, I advise international high-net-worth families, family offices, private banks and institutional clients. My work includes advising trustees, assisting with probate, wills and estate administration, advising on Cayman Islands Foundation Companies, and working on family office matters more broadly.
Q: How would you describe your typical workday?
A: One of the things I enjoy most about private client work is that no two days are the same. You’re rarely focused on a single matter from start to finish, so there’s a lot of variety in the day.
A typical day might involve drafting new trust instruments, drafting supplemental trust documents or deeds relating to an existing trust structure, reviewing underlying corporate structures and liaising with onshore counsel in relation to tax advice. Face-to-face client meetings are also a big part of the role, which I really enjoy.
It’s a very client-facing practice, and that’s one of the reasons I was drawn to private client work in the first place. The variety of matters, structures and client needs keeps things interesting and makes every day different.
Q: What inspired you to enter the industry?
A: For me, it was more about who than what. You’re very much a product of the people around you, and a lot of what inspires you comes from those closest to you.
In my case, that person was my late mother. She was a lawyer here in Cayman and worked for Hunter & Hunter, which has since become Appleby, so there’s a nice full-circle element to where I am today. She was really the reason I was drawn to the legal profession and ultimately to this career path.
Q: What do you enjoy most about working in the trust and private client sector?
A: There are two things that stand out for me.
First, it’s an incredibly people and relationship-oriented practice. You’re dealing with truly global families: the structure may be domiciled in Cayman, while the family’s assets and different generations of are spread across the world. Building relationships and understanding the people behind the structure is a big part of the work.
The second is the technical side. If you’ve studied equity and trusts, you’ll know there are always curveballs, whether you’re drafting trust deeds, assisting on acquiring assets for an established trust or advising trustees and investment managers generally. Trust law is technical by nature, and I really enjoy that intellectual challenge.
It’s also not a one-size-fits-all practice. Every family and every structure is different, therefore you’re constantly thinking about how to tailor the advice to the particular circumstances. That combination of technical complexity, client interaction and long-term relationship building is what I enjoy most.
Career Growth
Q: What’s been the biggest learning curve since you started your career?
A: Probably the transition from initial training into the realities of day-to-day practice as part of Appleby’s private client team.
You’re not just managing legal issues; you’re also managing expectations across different families, personalities and professional advisers. That means learning to tailor not only your advice, but also how you communicate and work with people.
Learning how to apply your knowledge in a practical, client-focused way has probably been the biggest learning curve for me.
Q: What surprised you most about working in the industry?
A: I was surprised by how intimate the trust industry is, particularly here in Cayman, but also on a global level. There are a relatively small number of practitioners in Cayman, so you naturally end up interacting with many of the same professionals regularly.
At the same time, the reach of the industry is genuinely global. Cayman may be a small jurisdiction geographically, but its trust industry has an international presence and reputation.
STEP Cayman is a great example of that. It’s a fantastic globally recognised branch and brings together practitioners from across the industry, while helping to promote Cayman as a leading trust jurisdiction.
Q: What skills have been most important in helping you succeed so far?
A: The first would have to be the training I’ve received at Appleby. The legal training here is second to none, and it gave me a very strong foundation from the outset.
Second would be people skills. I’m naturally a people person, and I really value connecting with others. Every client is different, and being able to establish that initial connection is an important starting point for building a strong relationship.
Third would be public speaking. It can certainly be daunting, but I enjoy the challenge, and it’s become an increasingly important skill for me over the past year. I was invited to speak on a panel at the STEP Cayman conference in January, and more recently spoke at another STEP event alongside my colleague on the role of protectors in trust structures.
Public speaking has helped raise my profile and visibility within the industry, which ultimately contributed to my recent nomination for the STEP Private Client Awards Rising Star (Legal). It’s been a really rewarding part of my development.
Q: What’s the most impactful feedback or advice you’ve been given, and how did you apply it?
A: A few pieces of advice have really stayed with me.
The first is that if you want something to happen, it’s your responsibility to make it happen. Take feedback from people who are willing to help and teach you, apply it, and then give it another go. It’s rarely perfect the first time, but that’s how you improve.
The second is to have confidence in yourself. Be solution-oriented, trust that you can deliver when a problem comes your way, and be confident enough to shake the client’s hand, ask the questions and take ownership of the issue.
The third is that being ready is a decision, not a feeling. You don’t have to be perfect or exceptional at something before you put yourself forward and give it a try. I come back to public speaking as a good example of that. You may feel uncomfortable at first, but that discomfort is often a sign that you’re learning and growing.
Q: Have you had any role models along the way?
A: I’ve definitely been fortunate to have a number of mentors along the way, although I won’t list them all for fear of leaving someone out.
My dad is a big one. He’s been in the financial services industry for over 30 years and has always been a great, balanced sounding board for me.
At Appleby, I was also fortunate to have a close relationship with our recently retired Managing Partner, Norman Klein, who has been a mentor to me. I’m equally fortunate to work with my current boss and the Global Head of our Private Client team, Carlos Pimentel. He’s an excellent and patient teacher, and I really value his depth of knowledge and experience in trust law.
Q: Was there a moment when you thought, “I can see myself building a future in this industry”?
A: It was fairly early in my practice, when I started working on a particularly memorable matter involving a high-profile Cayman trust structure that held a highly valuable original Andy Warhol piece of artwork.
The piece formed part of a larger private art collection and was intended to be used as collateral for further acquisitions, while also potentially being displayed to the public in New York. The trustee required advice on a range of issues to make the arrangement work.
Working alongside onshore and offshore counsel on something with so many moving parts, and involving such an interesting and tangible asset, made me realise how much I enjoyed that kind of work. It was engaging, technically interesting and involved professionals from a number of different jurisdictions.
I found myself wanting to come back the next day, learn more, work on the next deal and continue engaging with people across the industry. That’s when it really clicked for me that this was an exciting place to build a career.
Q: What are you still hoping to learn or achieve as you develop in your career?
A: It’s still relatively early days in my career, but I never want to stop learning. This is a dynamic and fast-paced industry, and I want to continue challenging myself while developing real depth and expertise in specific areas of the trust industry.
Ultimately, I want to keep learning, keep taking on new challenges and continue building my career here in Cayman for a long time to come.
Q: What excites you most about the future of the industry in Cayman?
A: It’s a really exciting time for the private client industry in Cayman. We’re seeing a lot of new business coming into the jurisdiction, and there’s a real sense of momentum across the industry. Cayman continues to go from strength to strength.
There’s also a significant generational transfer of wealth on the horizon, and I think Cayman is going to be front and centre of that. That should create a lot of interesting work coming into and out of the jurisdiction.
Advice for Young Caymanians
Q: Why should a young Caymanian choose trusts and private wealth as a career path?
A: I’d absolutely say this should be on the radar of any young Caymanian. You’re entering an industry that is in a significant growth phase, with plenty of work and excellent mentoring opportunities, not just on the legal side but across all the different roles that make the industry function.
It’s an opportunity to be part of that growth while building a long and dynamic career. You can get in early, learn from people who have helped shape the industry here for years, and develop your own place within it.
It’s also a relatively small pool of professionals compared with some other areas of financial services in Cayman, which creates genuine opportunities to diversify your skill set, build relationships and stand out.
Q: What steps should young Caymanians take to enter the industry?
A: For me, going away for my education was incredibly beneficial. It broadened my horizons, exposed me to different cultures and business perspectives, and helped build my confidence in ways I probably wasn’t even conscious of at the time. Coming back to Cayman with that outside perspective also helped me appreciate the industry here even more.
That said, you absolutely don’t have to leave Cayman to build a career in this space. There are excellent local options, including the Truman Bodden Law School. If you do have the opportunity to gain experience elsewhere, I’d encourage you to take it and bring that perspective back with you.
I’d also strongly recommend getting involved with STEP Cayman. There are excellent qualifications and designations available, as well as professionals who are genuinely interested in helping develop the next generation through initiatives such as the STEP Next Gen programme.
It’s a great way to build your network and get your foot in the door. That’s one of the real advantages of an intimate industry like Cayman’s: people are generally willing to help develop the next generation and have those conversations with you.
Get educated in the areas that interest you, speak to people working in the industry, ask questions and go from there.
Q: What advice would you give to a young Caymanian who’s just starting in the industry?
A: Be a sponge and stay open-minded. You’re there to learn, so don’t be afraid of making mistakes. Speak up, ask questions, shake people’s hands and network. Cayman offers incredible networking opportunities, and you never know where a conversation or relationship might lead.
One of the best things you can do from day one is become exceptionally good at whatever task is in front of you. If you can handle your day-to-day responsibilities confidently, efficiently and with increasing autonomy, you’re already putting yourself in a strong position.
Nothing worth doing comes easily, so be prepared to put the work in. But do it with a positive attitude and be a team player. People sometimes underestimate just how far being genuinely easy to work with can take you.
Q: What misconceptions do young Caymanians sometimes have about financial services, and trust and private client work specifically?
A: I think the biggest misconception is that this space isn’t accessible to young Caymanians. It absolutely is.
You don’t have to be a lawyer or an accountant to build a career in this industry. There are opportunities across financial services, from STEP qualifications and trust administration to investment management, compliance, regulatory roles and many of the other functions that support the industry.
There really is room for everyone. The key is figuring out what interests you, understanding where your strengths lie and then having the confidence to pursue it.
Q: Where do you see the biggest opportunities for Caymanians in the sector over the next five to 10 years?
A: I think the opportunities are almost limitless, particularly as the jurisdiction continues to grow.
Take a typical trust structure, for example. It’s not just the lawyers who make that structure work. You have trustees, investment managers, potential protectors, accountants, compliance professionals and regulatory specialists, among others, all playing an important role.
As the industry continues to develop, there will be opportunities across all of those areas. Caymanians have a real opportunity to build expertise, take on leadership roles and help shape the next generation of the industry.
Outside of Work
Q: What do you enjoy doing with your free time? Do you have any hobbies?
A: You’ll usually find me doing something active. I enjoy running, and I used to swim competitively in Cayman, so I still enjoy getting in the pool or heading to the gym.
I also try to travel somewhere exotic and outdoorsy at least once a year. On weekends, I like getting out on the water, whether that’s heading out on the boat with my brother and friends to Rum Point or going for a snorkel.
There’s really nothing better than an island weekend before coming back to work on Monday.
Q: Do you have a favourite book or film?
A: I read so much for work that I don’t get through as much recreational reading as I’d like, so I’ll offer a podcast recommendation instead.
I enjoy listening to a business-focused podcast on my way to work, something that gives you a good sense of what’s happening in the world and what you need to know for the day. I’d recommend Morning Brew Daily. It’s a great way to start the morning.
Q: Do you have a favourite restaurant in Cayman?
A: There are so many great options in Cayman, but a family favourite for us is The Falls Steakhouse. It’s a classic and always a good choice.
