Chief Executive Officer

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

Chief Executive Officer (Gaming Caribbean, relocation required)

Please note: Although this role is advertised in the US, this Role Is Based In The Caribbean And Will Require Relocation, unfortunately we can not offer remote working.

Based in the Caribbean, relocation required | Competitive salary, dependent on experience | C-suite leadership of a multi-channel gaming business

The opportunity:

We are headhunting alongside an established gaming operator with a broad multi-channel presence across the Caribbean, spanning retail distribution, company-owned outlets, and digital and mobile platforms. Following a period of sustained growth, they are seeking a Chief Executive Officer to lead the business through its next phase of digital transformation and market expansion.

This is a role for someone equally comfortable in the boardroom and on the ground.

Much of the business's commercial success comes from relationships built directly with retail partners, from independent bar owners to community stores, right across the distribution network. You will set the strategic direction while staying close enough to the relationships that genuinely drive revenue in this industry. Candidates currently based in Florida with strong Caribbean market experience or connections are encouraged to apply, provided they are open to relocating.

What you will be doing:

• Setting and delivering the company's long-term strategic direction in partnership with the Board.
• Overseeing a distribution network spanning retail partners, company-owned outlets, and digital platforms.
• Leading commercial and financial performance, including budgeting, forecasting, and EBITDA delivery.
• Acting as the primary point of contact with regulatory bodies and other key stakeholders.
• Building and leading a senior executive team across operations, finance, and technology.

What you will need:

• A minimum of 15 years of progressive senior leadership experience, including at least 5 years at C-suite or equivalent level.
• Experience within lottery, gaming, fintech, or another highly regulated retail or consumer sector.
• A strong understanding of Caribbean regulatory environments would be preferable, or a demonstrated ability to assimilate complex regulatory frameworks quickly.
• Genuine, on-the-ground relationships across Caribbean retail and community networks.
• A background spanning both digital platform growth and traditional retail distribution would be an advantage, as would prior experience reporting directly to a Board.

Location and relocation:

This is a Caribbean based, in-market role, not a remote or hybrid position. Relocation is a firm requirement, and full relocation support will be discussed directly with shortlisted candidates.

What is on offer:

• A competitive salary, dependent on experience.
• The opportunity to lead a business through a genuine digital transformation.
• Direct Board exposure and full accountability for strategic direction.