Caribbean-based CEO: Lead Digital Transformation & Growth

Thatcher Associates; Town of Florida (NY); On-site; USD 250,000 - 420,000; Full time

Benefits offered by this job

Relocation support

Board exposure

Digital transformation leadership

Job summary

Thatcher Associates is seeking a Chief Executive Officer for a Caribbean-based gaming operator. The role demands strategic leadership, P&L ownership, and close ties to Caribbean regulators and retail networks. Relocation is mandatory, with support discussed for shortlisted candidates.

You will drive digital transformation, expand market presence, and report directly to the Board. The candidate will balance boardroom oversight with hands-on leadership across operations, finance, and technology,

Qualifications

• 15+ years of progressive senior leadership experience, including at least 5 years at C-suite level.
• Experience within lottery, gaming, fintech, or another highly regulated retail or consumer sector.
• Strong understanding of Caribbean regulatory environments or ability to assimilate complex frameworks quickly.
• Genuine, on-the-ground relationships across Caribbean retail and community networks.
• Experience reporting directly to a Board and leading multi-functional teams.

Responsibilities

• Set and deliver the company's long-term strategic direction in partnership with the Board.
• Oversee a distribution network spanning retail partners, company-owned outlets, and digital platforms.
• Lead commercial and financial performance, including budgeting, forecasting, and EBITDA delivery.
• Act as the primary point of contact with regulatory bodies and other key stakeholders.
• Build and lead a senior executive team across operations, finance, and technology.

Skills

Strategic leadership

Board communication

Regulated sector experience

Caribbean market knowledge

Retail distribution

Digital transformation

Job description

Thatcher Associates is seeking a Chief Executive Officer for a Caribbean-based gaming operator. The role demands strategic leadership, P&L ownership, and close ties to Caribbean regulators and retail networks. Relocation is mandatory, with support discussed for shortlisted candidates.

You will drive digital transformation, expand market presence, and report directly to the Board. The candidate will balance boardroom oversight with hands-on leadership across operations, finance, and technology,