Chief Financial Officer

Windsor, an exclusive family-owned club and community located in Vero Beach, Florida, seeks a strategic and accomplished Chief Financial Officer (CFO) to lead its financial operations. Windsor presents an exceptional opportunity for a finance leader to guide a $30+ million operation serving 300 member families and 300 homes with both increasing to 350 s is a transformational leadership role requiring both strategic vision and operational excellence.

The successful candidate will partner with the General Manager to drive financial strategy, oversee a $30+ million annual budget, manage capital planning for ongoing facility enhancements, and ensure the Club's long‑term fiscal sustainability. The Club is anticipated to transition from family ownership to Member ownership within the next five years. The CFO provides executive leadership for Accounting, Finance, Human Resources, and Information Technology departments.

Windsor is at an important inflection point in its evolution, transitioning from its historical roots as a real estate development with club amenities to a fully member‑centric private club and community with significant real estate holdings.

Windsor serves 300 member families representing a distinguished membership of accomplished professionals, business leaders, and multi‑generational families from around the world. The Club maintains a warm, inclusive culture that balances social sophistication with family‑friendly programming. Members value tradition while embracing innovation, as evidenced by recent investments in racquets and fitness and wellness offerings.

• Annual Operating Budget: $30+ million
• Capital Investment Program:
  Multi‑year strategic capital plan focusing on facility enhancements and infrastructure
• Membership Structure:
  Family‑owned equity club with strong governance and fiscal discipline. Transition to Member ownership is anticipated within the next five years.
• Real Estate Portfolio:
  Real estate office represents buyers and sellers within Windsor as well as handling all sales of developer owned land.
• Staff: 250+ employees (peak season), 145 in the summer, including golf, tennis, aquatics, fitness, dining, facilities, and administrative teams
• Departments Under CFO:
  Accounting, Finance, Human Resources, and Information Technology

The Chief Financial Officer reports to the General Manager. The General Manager and CFO work closely with the ownership’s CFO and Sr. Director, Business Analysis based in Toronto. This role requires regular interaction with Club leadership and the ability to communicate complex financial matters clearly to diverse stakeholders.

• Financial Leadership & Strategy:
• Serve as the Club's senior financial strategist, providing thought leadership on long‑term financial planning, capital allocation, and fiscal sustainability
• Partner with the General Manager to develop multi‑year strategic financial plans aligned with Club initiatives and member value objectives
• Lead the financial aspects of Windsor's organizational transition from developer/real estate model to member‑centric club operations
• Lead scenario planning and financial modeling for major capital projects, membership initiatives, and strategic investments
• Evaluate and recommend financial structure improvements, including dues strategies, capital funding mechanisms, and reserve policies.

• Direct the annual budget process, coordinating input from department heads and ensuring alignment with strategic priorities
• Prepare comprehensive budget documentation and presentations for Board review and approval
• Monitor budget performance throughout the year, providing variance analysis and recommending corrective actions
• Develop and track key financial metrics and performance indicators

• Oversee all accounting functions including general ledger, accounts payable, accounts receivable, payroll, and member billing
• Ensure robust internal controls, segregation of duties, and compliance with accounting standards and club policies
• Manage month‑end and year‑end close processes, producing timely and accurate financial…