Board Project Lead

Heritage Holdings Group is re-opening our search for a Board Project Lead — a key role supporting our Board of Directors, who also serve as hands-on executives within our fast-growing, family-owned organisation. We are seeking a detail-driven, tech-savvy professional who can navigate shifting priorities, strong personalities, and the unique dynamics that often come with a family-run business.

This is an exceptional opportunity for a highly organised, confident individual who enjoys being at the centre of strategy, execution and communication.

This role offers an exciting and unique opportunity to work at the centre of strategy, operations, KPI management, and project execution. We are looking for someone who thrives in a dynamic, direct, and fast-paced environment, and who can serve as the steady point of structure, clarity, and coordination.

Heritage Holdings Group of Companies is a diverse organisation comprising property management, construction, real estate development, architecture, sales and marketing, finance, operations and compliance, HR, and equipment rental and trenching. The Board Project Lead will operate across all these functions, supporting Board members who also serve as department heads and senior executives.

• Align work between Board members, department heads, and executives across multiple business units
• Lead and track high-level Board strategic projects, ensuring timely follow-up on directives
• Facilitate Board meetings, including agenda preparation, briefing materials, minutes, and action tracking
• Drive KPI monitoring and reporting to support organisational performance and accountability
• Serve as a communication bridge between governance and operations
• Optimise and maintain Asana and other project management tools
• Provide high-level IT and technical support for Board and executive needs
• Maintain confidentiality and exercise strong judgement at all times

This is a high-impact role that relies on exceptional organisation, strong communication skills, and the interpersonal maturity to guide multiple moving pieces with confidence and clarity.

Applicants must have a minimum of five (5) years of experience in project management and/or executive-level support. This experience is essential to handle the complexity and cross-functional demands of the role.

Additional requirements include:

• Bachelor’s degree in Business Administration, Project Management, IT, or a related field
• Strong proficiency in Asana or similar project management tools
• Advanced IT capability (Microsoft Office, virtual meeting tools, troubleshooting)
• Demonstrated ability to track KPIs and produce data-driven insights
• Excellent written and verbal communication skills
• Proven ability to work independently with a proactive, solutions-focused mindset
• Ability to manage sensitive information with absolute discretion

• Salary
  • KYD $67,200 – $84,080 annually (dependent on experience and qualifications)
• Benefits Package
  • We provide a competitive salary and a solid benefits package, including employer-supported insurance, statutory pension contributions, company-provided equipment and paid leave in accordance with Cayman Islands labour legislation.

This package reflects our commitment to supporting your well-being, productivity, and work-life balance.

• Direct exposure to the Board and senior leadership
• High visibility and meaningful influence across the organisation
• Opportunity to build new processes from the ground up
• A dynamic environment where your impact is immediate and tangible
• Unique experience in a family-led, multi-division organisation