The Organization

Cypress Woods Golf & Country Club is a 787 door, all-inclusive Private golf community in North Naples. Established in 1999, Cypress Woods has grown to be a top choice for bundled communities in the Southwest Florida area. As an owner in a bundled community, a full Golf Membership is bundled into the purchase of the home, whether it is a single-family home, coach home or condo. This cost-effective option allows owners to enjoy unlimited year round golf on the Gordon Lewis designed 18 hole course as well as club amenities including eight pickleball courts, one tennis Court, three bocce courts and a fitness center as well as a large resort style pool and hot tub. Every homeowner in the community is a Golf and Social Member of the Club.

Cypress Woods offers a variety of social clubs, games and activities designed to bring members together through shared interests and a strong sense of community. From weekly card games to seasonal events, there is always something happening. Popular gatherings include Bingo, Bunco, Chicago Bridge, Hand & Foot, Euchre and Pinochle, as well as water aerobics held regularly at the lap pool. For those who enjoy reading, the Book Club meets monthly in the Clubhouse Library during season. The Cypress Woods Wine Club offers curated experiences for wine enthusiasts of all levels, with exclusive tastings and events throughout the year.

The Club is governed by a nine person Board of Directors who have nine committees: Audit, ARC, Finance, Golf, Governance, Greens and Grounds, House, Recreation and Strategic Planning. Each department head works in conjunction with one or more of the operating committees of the Club.

VISION STATEMENT

To be an exceptional and vibrant golf and country club community that embraces forward-thinking values, offering top-tier golf, recreational, dining and social experiences in a warm and inclusive environment. We are dedicated to continuous improvement, fiscal responsibility focused on the upkeep of our Club assets and delivering the highest level of member satisfaction.

CYPRESS WOODS GOLF & CC DETAILS:

• Gross Dollar Volume: $10.8M
• Dues Volume: $6M
• F&B Volume: $1.9M
• Direct Reports: 1
• Full-Time Staff: 55
• Number of Employees in Season: 104
• Rounds of Golf: Approximately 40,000

Position Overview

The Director of Finance (DoF) is an important and integral member of a tight knit and well-established senior staff. It is the position that is depended upon by all parties including the General Manager, the management team and the Board of Directors to ensure the Club has the proper controls, administrative and reporting procedures and people systems in place to protect the assets of the organization and to ensure the financial strength and operational efficiency. The Director of Finance reports directly to the General Manager.

Maintaining accurate records is the basis of this position. However, timely and thoughtful analysis of financial results is key to making the proper impact on both short-term and long-term strategic decision-making. There are significant capital project about to commence in April of which appropriate proactive policies and controls and up to the minute record keeping will be of utmost importance. The successful Director of Finance will be an energetic, forward-thinking and creative individual with high ethical standards and an appropriate professional image. This person will be discreet and behave with a high degree of professionalism, with a thorough understanding of finance, accounting, budgeting and cost control principles, including generally accepted accounting principles.

Under the guidance and direction of the General Manager and within the limits of the Cypress Woods Golf & CC's policies and procedures, the Director of Finance develops the strategic direction of the Accounting Department and manages all financial aspects of the Club. The DoF will optimize traditional finance planning and analysis, auditing, compliance, treasury, financial reporting and project tracking. When and where appropriate, the DoF will develop transformative and automated processes/systems that have a positive impact on the business.

Responsibilities

• Prepare the annual operating and Reserve budget for consideration of the General Manager.
• Administer the approved budget; tracking and communicating variances in a timely manner and working with management team to identify causes, remedies or trends. Update forecasts when necessary.
• Manage and oversee the gathering of information, calculation and preparation of the organization's payroll.
• Manage the processing of member transfers and fee collection.
• Manage the employee insurance program ensuring the proper application of benefits to qualified employees.
• Prepare financial reports covering, but not limited to insurance, tax status, budgets and cash flow. Assist General Manager in the preparation of the annual capital and operating expense budgets and estimate of revenues to be received.
• Maintain all membership records in an efficient, accurate and secure manner.
• Manage and solve the problems with membership billing in a courteous and efficient manner in person, by phone, online or written correspondence.
• Work with the Club's external auditors to ensure that the Club's approved policies and procedures are applied consistently and that the appropriate federal tax returns are properly filed.
• Prepare all necessary federal, state and local agency reports not processed by the external auditors and by the payroll processing company.
• Maintain all insurance records covering Club property. Assist the General Manager in researching competitive bids on insurance policies.
• Ensure proper policies and processes are in place and followed for the taking of inventories within the Club's profit centers.
• Maintain the official personnel records of all employees in an efficient and secure manner.
• Supervise staff to ensure efficient and courteous operation of the department.
• Conduct annual performance reviews with accounting staff. Recommend salary adjustments to the General Manager.
• Aid in Human Resource responsibilities.
• Banking functions including bank reconciliation monthly to be approved by the GM.
• H-2B Visa Program Management, ensuring full compliance with federal and state regulations:
  • Coordinates with legal counsel, recruiters and government agencies to process applications, extensions and audits.
  • Develops and monitors the H-2B budget, including recruitment costs, transportation, housing, and related reimbursements.
  • Maintains accurate records, deadlines and documentation required for filings and compliance reviews.
  • Works closely with department managers to forecast seasonal labor needs and ensure alignment with operational budgets.
• Takes on other tasks and responsibilities as requested by the GM.

Attributes

• An outgoing and friendly personality with a high potential to identify with and embrace the Club's unique culture.
• Highly energetic; a self-starter with a "hands-on" approach to management.
• A strong sense of service with proven staff development and training skills.
• Ability to establish and maintain effective working relationships with all staff. Teamwork is the foundation of the Club's success.
• Resolves common problems and challenges regularly with high judgment.
• Determines the best method to achieve goals and maintains the flexibility to ensure effective delivery of work. Continuously delivers high-quality results and is resilient in the face of obstacles.
• Fosters a collaborative team spirit. Actively helps and supports others. Deals with conflict in a positive manner.
• Understands all the key departments and functions and how they work collectively to achieve larger goals. Provides advice, information and direction to others to support the achievement of team and/or department goals. Recommends optimal approaches to address critical issues in the immediate and medium-term.
• An intelligent and articulate individual who can relate to people at all levels of an organization and possesses excellent written and oral communication skills. Must be able to communicate policies, procedures, regulations, reports, etc., to staff, members and guests.
• Remain open to others' ideas and exhibit a willingness to try new things.
• Possesses a good sense of humor, the ability to have fun and the genuine desire to raise the level of experience for all members and staff.

Requirements

• A Bachelor's Degree in Finance or a related field and experience that provides the required finance knowledge, skills and abilities.
• Seven to ten years of minimum experience as a CFO, Director of Finance, Controller or similar position at a club/HOA or within a similar hospitality environment, resort or hotel.
• Demonstrated success in software implementation and process improvement initiatives. Proficiency with Jonas is a plus.
• 7+ years of accounting experience in balance sheet reconciliation, accruals, G/L accounts, journal entries, variance analysis, preparing monthly financial reports, budgeting, bank reconciliations, preparing tax returns, annual audit preparation, forecasting, payroll, AR/AP, cash flow, policy and process development.
• Solid knowledge of FASB standards and GAAP.
• Understanding of appropriate rules pertaining to FS 720 organizations.
• A career path marked with stability and professional achievement.
• The professional will be a lifelong learner, continuing research and understanding industry trends. Excellent verbal and written skills.
• Effective coaching/supervision/training of staff.
• The ability to operate a computer to enter, retrieve, or modify data utilizing Microsoft Word, Excel, Outlook, PowerPoint, email, internet and other software programs at a high level of proficiency. Strong data analysis skills.
• Impeccable and verifiable references. All candidates will be subject to a thorough background check and drug test.

Competitive Compensation

• Competitive compensation/salary and an excellent performance bonus
• Health, Dental, Vision and Life insurance – costs and benefits as outlined in the Club's Summary Plan description
• Paid holidays, sick days and vacation according to Club policy
• Participation in the Club's 401(k) plan
• Employee meals and usage of Club facilities per policy
• Professional dues, educational allowance expenses
• Relocation assistance (if from outside the area)

To be Considered

To be considered for this outstanding opportunity, all cover letters and resumes should be received by February 20, 2026. All information received will be kept in the strictest confidence.

Professionals who meet or exceed the established criteria are encouraged to send a compelling cover letter addressed to Ms. Grace Lennon, LCAM, General Manager, outlining their qualifications, experience, interests and why the Cypress Woods Golf and CC and Naples area of Florida will be beneficial for you, your family, and your career, along with their resume, to:

Thomas J. Noyes, CCM, CCE
Principal
tnoyes@gsiexecutivesearch.com
941-525-3211