Given the evolving landscape in financial services, and the need to attract and retain talent in the financial services industry, AIMA is investing in creating a pipeline of diverse talent in the industry at the pre-career stage with CareerMasters.

The financial services industry in the Cayman Islands, long renowned for its robust legal framework, sophisticated infrastructure and extensive global reach, continues to demonstrate its resilience as it adapts to the demands of the current global markets and evolving workforce needs. Given the pivotal role the Cayman Islands' financial services sector plays in the global economy, maintaining a dynamic and skilled workforce to serve its sophisticated international clientele is essential. However, like many industries worldwide, it is forced to navigate evolving career ambitions with each generation of employees and rapidly shifting technological advancements. Attracting top junior talent in such a competitive environment necessitates innovative approaches that extend beyond traditional recruitment methods.

This article explores some of the key drivers behind the workforce challenges in the industry and examines how AIMA and CareerMasters, a new initiative in the Cayman Islands that embraces a hands-on approach to training and local work experience placement, are addressing these issues.

Empowering Future Financial Leaders through CareerMasters

Recognising the need to identify talent at an early stage and provide career opportunities within the local financial services industry, CareerMasters emerged in 2024 with the mission of empowering pre-career individuals through guided mentorship and leadership training. It is quickly gaining a reputation as a cornerstone programme in shaping the next generation of financial services professionals.

In collaboration with AIMA Cayman, the programme aims to foster a sustainable pipeline of talent for the sector. Tim Rossiter, Chairman of AIMA Cayman, believes that the partnership with CareerMasters reflects AIMA Cayman's commitment to education. "This collaboration will create accessible pathways for the personal growth and success of many young Caymanian students who are interested in pursuing careers within this field by empowering them to advance their career prospects and positively contribute to our community."

CareerMasters is led by Christina Bodden, a Partner with the Maples Group, and Kelly Sage, Owner of Rampd Consulting. Both Christina and Kelly sit on the Board of Directors of CareerMasters and work alongside partners from AIMA Cayman and several key stakeholders within the Cayman Islands Government, including representatives from the Cayman Islands Ministry of Education; the Cayman Islands Ministry of Youth, Sports, Culture and Heritage; and the Cayman Islands Ministry of Border Control, Labour and Culture. Together, the group are working towards one common goal: to create tangible opportunities for early career development and a sustainable workforce in the Cayman Islands financial services industry.

Speaking to how CareerMasters originated, Christina said, "We identified a gap at the entry level within the local finance sector. Through extensive research, we learned that young people often perceive the industry and its related careers as daunting; they are unsure of where or how to begin a career in this field, leading them to seek opportunities elsewhere. This represents a lost opportunity for both the individuals and the industry."

Through a combination of tailored workshops, one-on-one support, business mentorship and work experience placements, CareerMasters aims to create opportunities for its participants to gain invaluable exposure and to demystify any preconceived notions about careers in the financial services industry.

"We hope that this holistic approach will make the industry more accessible and less intimidating for those at the start of their career journeys and will help to enhance critical skills such as communication, problem-solving and leadership," Christina added.

The True Value of Partnerships

The impact of CareerMasters extends beyond individual participants. One of the most remarkable aspects of CareerMasters is that mentors from within the financial services industry play a crucial role by sharing their own expertise and inspiring mentees to envision long-term careers in the industry.

"These mentors are instrumental in equipping young professionals with the skills and expertise needed to thrive in the competitive global market," Christina highlighted. "It also ensures that the expertise of seasoned professionals in the funds and financial services industry is passed down to the up-and-coming generation, creating a continuous cycle of growth and development within the local workforce."

In addition, CareerMasters works closely with local high school teachers to select the most appropriate students to participate in the programme, who are chosen based on their demonstrated inclination for a career in financial services and / or whether they have the requisite skill set. This partnership ensures that the programme reaches those who are most likely to benefit from inclusion.

As we look to the future, the partnership between industry leaders, educational institutions and initiatives such as CareerMasters will be crucial. By investing in local talent and workforce development, CareerMasters is future proofing the Cayman Islands' financial services sector, creating a competitive advantage for the jurisdiction and making a significant and positive impact on the local community.

To that effect, the support of the Cayman Islands Government is instrumental in the success of the programme. Franz Manderson, Deputy Governor of the Cayman Islands, said: "The Cayman Islands' financial services sector is a cornerstone of our economy, and its continued success hinges on attracting and developing top talent. CareerMasters is a vital investment in our future, providing young Caymanians with the skills, mentorship and opportunities needed to thrive in this dynamic industry. By fostering a pipeline of diverse local talent, CareerMasters is not only strengthening our financial services sector but also building a brighter future for our community as a whole."

Challenges in Talent Management in 2025

Creating an industry-wide workforce that is self-sustaining is more critical than ever before. According to the Harvard Business Review[1], a large portion of employees in the industry will be eligible for retirement in 2025. The report stated that the surge in retirements supersedes "any previous year on record, draining organisations of their most experienced employees at an accelerated rate."

The report also noted that this situation is further complicated by the impact of artificial intelligence, which may be viewed as a technological disruption to older generations and has altered the dynamics between expert and novice employees across various industries. The author shared that AI has taken over "many of the functions previously provided by interns and support teams, leaving junior employees without the opportunities they need to learn and build expertise." This has contributed to the challenges faced by pre-career and junior employees in accessing entry-level positions and training opportunities that were once readily available.

Conversely, the concept of learning "in the flow" of work is becoming increasingly important, particularly for younger employees who expect on-the-job training as part of their development. KPMG[2] notes that while "learning in the flow of work remains an abstract concept for many organisations…the idea recognises that effective learning needs to happen on the job. Instead of introducing separate training sessions, employees learn the specific skills or knowledge at the time they need to do their jobs."

These trends have resulted in many financial services businesses developing bespoke training programmes for new recruits and junior hires to bridge the experience gap or enhance their job-focused training. This has also underscored the value of early or pre-career programmes, such as CareerMasters, which provide training and business acumen awareness even before internships or job placements. Financial services firms heavily support such programmes as a supplement to their own training efforts and as a means of identifying top junior talent for recruitment. 

Participant Progress and Impact Reporting

CareerMasters places a strong emphasis on feedback from its participants, local stakeholders and partners. By compiling and analysing this feedback, the programme can showcase the readiness and capability of its participants. This feedback, collated by the programme's governance sector and reflected in its quarterly impact reporting, is crucial for identifying areas of improvement and ensuring the programme remains relevant and effective.

As participants advance through the programme, they grow in confidence, become more adept at navigating the industry and are better able to identify which career path is most appealing to them.  "Investing in youth mentoring is not just socially ethical; it’s an economic imperative. When young people receive guidance, support and opportunity, they develop the confidence and skills to contribute meaningfully to the workforce, driving long-term financial and societal success," said Kelly.

Initial feedback from the students has been both positive and encouraging. In a time when youth mental health is a matter of national concern, the programme focuses on emotional well-being, resilience and self-confidence. 

CareerMasters: Long-Term Success for the Next Generation

CareerMasters is more than just an initiative; it is a movement dedicated to highlighting the critical importance of supporting individuals before they embark on their professional journeys and places a strong emphasis on encouraging young people to pursue roles within the local financial services sector, recognising the sector's potential to offer rewarding and sustainable career paths.

Locally, CareerMasters is strengthening the Cayman Islands economy by creating job opportunities and fostering a skilled workforce. Globally, it positions the Cayman Islands as a leader in the funds and financial services industry, showcasing its commitment to excellence and innovation. This local-global hook is a powerful framing that underscores the significance of the initiative and its far-reaching benefits.

CareerMasters is registered under the Non-Profit Organisations Act (2020 Revision). For more information about CareerMasters or to discuss partnership opportunities, contact Kelly Sage at [email protected]. Together, we can create a brighter future for the financial services industry in the Cayman Islands.