Human Resources Manager

About Cayman First: ‘First’ is more than our name, it’s our nature. Cayman First is an industry-leading Property & Casualty and Health insurer, delivering best-in-class products and services to respond to the changing needs of individuals, households and businesses. Through our carefully selected network of agents and brokers, we provide protection for our customers today and prepare them for a brighter tomorrow. Cayman First maintains an A- (Excellent) financial strength rating from global credit rating agency AM Best. Human Resources Manager The Role: We are seeking an experienced and dynamic Human Resources Manager to join our leadership team. This pivotal role acts as a strategic partner to executive management, with responsibility for overseeing all aspects of human resources. The successful candidate will drive key initiatives such as performance management, employee training and development, immigration processes, and payroll administration, ensuring full alignment with local regulations and organizational objectives. The Human Resources Manager will also play a critical role in preparing reports for the Board, spearheading continuous improvement through HR projects, and managing external vendor relationships to deliver effective, compliant, and high-impact HR services.

Job Responsibilities

• Lead the development, implementation, and ongoing evolution of the organization’s Human Resources strategy, ensuring alignment with business objectives, organizational values, workforce planning requirements, and approved budgets.
• Provide overall strategic and operational oversight of the HR function, ensuring efficient delivery of core HR services, effective management of HR staff, and consistent application of policies, procedures, and governance standards.
• Serve as a trusted advisor to executives and managers on employee relations matters, including performance management, conflict resolution, disciplinary processes, and workforce risk mitigation, ensuring fair and legally compliant outcomes.
• Oversee compensation, benefits, and payroll programs to ensure market competitiveness, internal equity, cost control, and accuracy, supporting attraction, retention, and motivation of employees.
• Ensure organizational compliance with all applicable employment, immigration, pension, health insurance, and regulatory requirements, including coordination of audits, maintenance of documentation, and proactive identification of compliance risks.
• Lead recruitment and workforce planning activities, partnering with business leaders to attract, select, and onboard talent aligned with organizational needs, culture, and long-term capability requirements.
• Oversee performance management frameworks, employee evaluations, learning initiatives, and career development processes to support individual growth, succession planning, and organizational effectiveness.
• Design and implement training and development initiatives that enhance leadership capability, technical skills, and employee engagement while supporting succession planning and future workforce needs.
• Champion organizational culture and employee engagement initiatives, including onboarding, staff engagement programs, internal committees, and cultural events that promote collaboration, inclusion, and retention.
• Oversee general office operations and support services, ensuring smooth administrative processes, effective front-office management, and a productive and professional work environment.
• Prepare and present HR metrics, reports, and strategic insights to senior leadership and the Board to support data-driven decision-making and organizational planning.
• Carry out other related duties and cross-functional responsibilities as assigned in support of organizational objectives.

Qualifications & Experience

• Bachelor’s degree in Business Administration, Psychology, Human Resources Management, or a related field.
• Minimum of 5 years as a Human Resources Manager.
• Experience in the Financial Service industry preferred.
• Recognized HR designation (e.g., SHRM-CP or equivalent).
• Demonstrated experience developing and executing HR strategies and budgets aligned with corporate goals.
• Strong background in employee relations, compensation and benefits, payroll oversight, and regulatory compliance.
• In-depth knowledge of Cayman Islands Labor, Immigration, Pension, and Health Insurance legislation.
• Proven experience managing audits, performance management systems, training programs, succession planning, and onboarding.
• Extensive experience with full-cycle recruitment and immigration processes.
• Proficient in Microsoft Office, HRIS, payroll systems, and HR technologies.
• High level of discretion and confidentiality.
• Excellent interpersonal, communication, time management, and organizational skills.
• Self-motivated, assertive, and capable of working effectively under pressure.