Chief Financial Officer

Chief Financial Officer (CFO)

Location : Remote

Compensation : $250k-$300k

About the Company

We are a privately held, entrepreneurial group of companies generating approximately $10 million in annual revenue across operations in the U.S., Canada, and Barbados .

Our portfolio includes businesses in healthcare, technology, and professional services , with three active operating entities and plans to expand into new sectors and geographies. Each business operates with its own management team, while the Group CEO and COO oversee shared strategy, performance, and growth.

The organization has a strong track record of profitability and is backed by a long-term principal who is focused on building a sustainable, diversified platform capable of scaling significantly over the next five years.

The Opportunity

As a $10M organization entering its next stage of growth, we are seeking a Chief Financial Officer (CFO) to bring financial leadership, structure, and strategy to a dynamic multi-entity environment.

This is both a strategic and hands-on role - ideal for a finance executive who thrives in entrepreneurial settings, enjoys building systems and teams, and has experience scaling organizations with multiple lines of business.

Reporting directly to the CEO, the CFO will be a key member of the executive leadership team, overseeing finance, accounting, compliance, and capital planning while partnering on expansion, investment, and M&A activity.

Key Responsibilities :

Financial Leadership & Strategy

Serve as a trusted partner to the CEO, providing financial insight and strategic guidance to support long-term growth and profitability.

Lead all aspects of financial planning, budgeting, forecasting, and performance management across the group.

Develop and manage key banking, financing, and investor relationships.

Advise on capital structure, debt vs. equity financing, and working capital optimization.

Operational Finance & Team Development

Oversee the day-to-day finance and accounting operations across multiple entities.

Build scalable processes, systems, and internal controls to support growth and ensure timely, accurate financial reporting.

Mentor and develop finance team members, including a recently hired Controller.

Implement consistent reporting frameworks and KPIs across all business units.

Governance, Risk & Compliance

Oversee compliance, legal, and risk management across the group of companies.

Ensure proper financial governance and reporting standards are in place.

Support the development of financial policies and procedures that create structure without slowing down the business.

Growth, Expansion & M&A

Support strategic initiatives including U.S. and European expansion .

Evaluate and integrate new acquisitions or partnerships.

Build financial models and conduct due diligence for potential investments.

Help identify and pursue opportunities to diversify and stabilize revenue streams.

Qualifications

10+ years of progressive finance leadership experience , including 3-5 years as a CFO, VP Finance, or equivalent.

Experience in multi-entity or multi-sector organizations ; exposure to healthcare, tech, or services industries a plus.

Proven success implementing financial systems, reporting frameworks, and controls in entrepreneurial or growth-stage companies.

Strong grasp of cash flow management, forecasting, and capital strategy .

Experience with fundraising or debt financing preferred.

CPA, MBA, or CFA designation strongly preferred.

Leadership Attributes

Strategic thinker with strong business judgment and financial discipline.

Entrepreneurial mindset - comfortable operating in evolving environments with multiple priorities.

Collaborative, approachable, and confident working closely with owners and senior leadership.

Strong communicator who can translate financial concepts into actionable business insights.

Hands-on, resourceful, and motivated to build for scale.

Why Join

This is a rare opportunity to step into a high-impact executive role at an inflection point in the company's growth. The Group CFO will have the autonomy to shape the finance function, help mature the organization, and play a key role in strategic expansion and long-term value creation.

You'll be joining a profitable, entrepreneurial, and ambitious $10M organization - one that values partnership, initiative, and the drive to build something enduring.

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