CareerMasters Celebrates Transformative First Year Empowering Cayman Islands Youth

CareerMasters, the Cayman Islands’ leading pre-career programme for high school students, proudly announces the successful completion of its inaugural year, marked by significant achievements in youth empowerment, community engagement, and career readiness.

Empowering the Next Generation

Launched to bridge the gap between education and employment, CareerMasters delivered a dynamic three-module programme that equipped students with essential workplace skills, fostered community involvement, and provided hands-on work experience. Over 150 students participated across Grand Cayman and Cayman Brac, gaining exposure to key industries and building the confidence to pursue ambitious futures.

Co-founder Christina Bodden, Partner at the Maples Group’s law firm, Maples and Calder, remarked, “This year, we saw students grow into confident, career-ready individuals with clear goals. Our first year has laid a powerful foundation for what’s to come in youth pre-career readiness and employment opportunities in the Cayman Islands. We were also excited to make this an inclusive and equal access programme, delivering it in-person to students at the Layman Scott High School in Cayman Brac –reaffirming our commitment to ensuring all students, regardless of location, are equally prepared for the workplace.

Programme Highlights

• Module 1: Formal Learning & Workplace Readiness: Students developed professional communication, resume writing, and interview skills, and explored various industry sectors. This module laid the groundwork for personal branding and career confidence.

• Module 2: Community, Philanthropy & Group Work: Through philanthropic projects, including work with the Cayman Islands Cancer Society, students built leadership and teamwork skills, with a focus was on empathy and initiative.

• Module 3: Work Experience: Every participating student was placed in a tailored internship, gaining real-world experience in fields such as finance, law, hospitality, and technology.

Chair of AIMA Cayman and key supporter, Tim Rossiter stated, “CareerMasters has been a shining example of what’s possible when the private sector comes together to invest in young people. This inaugural year has delivered real impact—connecting students with industry leaders, building confidence, and helping to shape the next generation of Cayman’s talent. AIMA is proud to support a programme that is not only innovative but truly transformational.”

FutureFlex: A New Kind of Career Conference

The year culminated in the landmark FUTUREFLEX conference, held on 26 June 2025 at Hotel Indigo.  Over 150 students and dozens of employers connected through interactive sessions and networking. Sponsored by the Maples Group (platinum sponsor), Baraud International, KPMG, PWC Conyers, Butterfield Bank, Zedra Cayman Islands, Carey Olsen, Ogier, Cayman National Bank and the Cayman Islands Rugby Club, the event featured student-moderated panels and was attended by distinguished guests that included the Honourable Rolston Anglin, Minister of Finance & Economic Development and Education & Training, and Acting Governor, Franz Manderson.

In a bold departure from the typical youth “career fair” format, the event hosted a panel of industry speakers moderated by CareerMasters students, with topics covering career journeys, navigating workplace challenges and advice seasoned professionals would give their younger selves. Students also gave ‘sound bite’ overviews of their experiences in the programme, and guest speakers offered their own personal journeys. The conference also welcomed local neuro psychologist, Dr Laurance Vanhanswijck, Kidsability, who presented a synopsis of the Penn Resilience Programme.

Minister Anglin noted, “The Ministry of Education is proud to partner with CareerMasters in its mission to empower high school students with skills, and pair that with opportunities. We look forward to our continued partnership as CareerMasters continues to grow and expand its offering, aligning with the Ministry’s own robust agenda for Cayman’s youth population.”

The CareerMasters Leaders Award recognised students who demonstrated the highest development of leadership skills throughout the CareerMasters programme, in their practical skills, their collaboration with colleagues and their approach to new workplace challenges. Acting Governor, Franz Manderson presented these awards to Kimora Stewart (John Gray High School), Charlee Hernandez (Cayman Prep and High School), Zenna Jacobs (CHHS), Aryan Champawat (Layman Scott High School), Travis Green (Clifton Hunter High School), Herbert Walker (JGHS) and Chelsea Whittaker (St. Ignatius Catholic School).  The programme’s premier recognition, The CareerMasters Star Award, was pesented to John Gray High School Student, Nyomi Myles, who most embodied the mission and values of CareerMasters through their overall leadership, ‘one team’ approach to fellow students and colleagues and outstanding professionalism to employers and stakeholders.

Mr. Manderson commented, “I was proud to recognise so many of our Cayman Islands civil servants at CareerMasters FutureFlex Career Conference, providing guidance and advice to high school students interested in careers within the Cayman Islands civil service sector. A huge thank you to my own team for their participation in this event, and congratulations to CareerMasters on its achievement for our Cayman Islands youth. Looking forward to working together as we move forward.”

Looking Ahead

CareerMasters is excited to announce two new initiatives:

• CareerMasters Futures Ball: In September, the programme will host its first signature gala dinner, focused on raising funds to expand access and opportunities for Caymanian youth.

• CareerMasters Alumni Society: To deepen connection and continue the journey, CareerMasters will also launch its Alumni Society — a growing network of young professionals and student leaders who have completed CareerMasters and are committed to paying it forward. The society will offer mentorship, community service, and ongoing career support.

Co-founder Kelly Sage, Founder of Rampd Consulting, emphasized, “We are here to inspire students to raise the bar, ignite their ambition, and expand their vision for what’s possible.”

About CareerMasters

CareerMasters is a non-profit initiative dedicated to preparing Cayman Islands high school students for successful careers through skills training, community engagement, and real-world work experience. Founded by Christina Bodden and Kelly Sage, CareerMasters partners with leading employers, educators, and community organizations to empower the next generation of Caymanian talent.

Contact: hello@career-masters.com