Empowered Voices: Caymanian Women Leading the Way at Appleby

Caroline Barton, Partner, is widely respected and recognised by leading legal directories.  She believes success in law requires “interpersonal qualities, integrity and effective communication,” and that it is for leaders and decisionmakers to recognise those qualities in any employee, reward performance and ensure opportunities are equitable as women deserve to be equals, not different”.  She emphasises the importance of cultivating confidence through “self-awareness, a supportive network, owning your achievements and having direct conversations.” Reflecting on her 25-year journey with Appleby, Caroline finds the most rewarding aspect to be her own professional growth alongside the firm and having the ability to continue its legacy.  As a member of the Scholarship Committee, she now sits where those “who opened the first door to her career sat to ensure those same opportunities are available to many others”.  She advises that “mentorship is a two-way street and encourages women to seek out sponsors who will advocate their progression and to “remain patient, initiate and maintain relationships and always aim to lead by example”.

Appolina Winton, Senior Associate, is a rising force in the industry. She has been recognised as a 2024 Fund Finance Association Rising Star and a 2024 CIRCA Rising Star. Appolina credits her success to “determination, adaptability, and reflection,” qualities that help her find solutions and grow professionally. Passionate about mentorship, she dedicates time to training interns and speaking at school fairs, empowering future legal professionals.

Ann-Alecia Duval, Senior Associate, is a committee member of 100WF Early Careers and thriving in her practice, advising clients on complex corporate matters with confidence and expertise. Ann-Alecia believes that “it is crucial for young women to have role models for guidance and inspiration—someone they can relate to within their firm or the wider legal community.”

Alexandra Jennings, Associate, highlights “confidence, learnability, and communication” as essential skills in the evolving legal landscape. She attributes her growth to “continuous learning and collaboration” and hopes to inspire others to pursue their passion for law. As a junior lawyer, Alexandra values mentorship both as a mentee and mentor, prioritising “paying it forward” by guiding younger colleagues.

Appleby is proud of Caroline, Apple, Ann-Alecia, Alexandra, and all the remarkable women on our team who continue to lead with confidence, shape the legal profession and make invaluable contributions to our industry. They are not just part of the conversation—they drive it, embodying the strength, intelligence, and resilience that define Caymanian women.

First published by Cayman Compass, CayWoman 2025. Download the feature below.