Club Details

Chicago Yacht Club

400 E Monroe St
Chicago, IL 60603

Unique Club/Facility Details

The Chicago Yacht Club was founded in 1875, and has a rich nautical history, including running for over a century the Race to Mackinac, the longest annual freshwater sailboat race in the world. The Club maintains a fleet of over 120 boats, hosts a myriad of on-the-water activities, and provides world class nautical education to youth and adults through its Sailing School. The Club’s 1,250 members complement their on-the-water activities with top notch indoor and outdoor dining at the Club’s two locations - the Monroe Station (downtown Chicago) and Belmont Station (Wrigleyville area). Chicago Yacht Club is recognized as a top five Platinum Club in the United States and has annual revenues more than $9 million.

Since its founding, the CYC has been the premier social and racing destination for Chicago area boaters and those passionate about being on the water. The Club is ranked as one of the 6 top yacht clubs in the U.S. by the Platinum Club of America. 

We have a membership of 1,250 boating enthusiasts who are active in the Club. From juniors (our youngest is just 7 years old) through veterans who have been part of the Club for decades, CYC members plan and participate in dozens of social, educational and racing events held throughout the year at our Monroe and Belmont stations — both located on Chicago’s iconic lakefront.

The Chicago Yacht Club Foundation, the cornerstone of our community outreach, promotes awareness of nautical arts to the Chicagoland community through education, activities and support of charitable organizations. 

CYC organizes preeminent regattas that consistently attract some of the best competitive sailors from around the world. The Chicago Yacht Club Race to Mackinac, a century old 333-mile sailing race from Chicago to Mackinac Island, MI, is our signature event that hosts approximately 300 boats and 2,750 sailors each year.

Club is open 6 days per week, 12 months per year.

Age of Club: 150
Number of Members: 1250
Average Age of Members: 58
Club Ownership: Member-Owned
Gross Dollar Volume: $9,000,000.00
Annual Dues Volume: $4,100,000.00
Annual Food Sales: $2,500,000.00
Annual Beverage Sales: $1,000,000.00
This club uses CMAA's General Manager/Chief Operating Officer Concept.

Golf Facilities

None

Racquet Facilities

None

Swimming Facilities

None

Other Athletic Facilities

Dining Facilities

  • 1 Monroe - Formal Dining Room that seats 150
  • 1 Monroe - Informal Dining Room that seats 50
  • 1 Monroe - Lounge/Bar that seats 50
  • 1 Monroe - Outdoor Dining that seats 100
  • 1 Monroe - Private Function Room that seats 80
  • 1 Monroe - Meeting Room that seats 30
  • 1 Belmont - Casual Dining Room that seats 150
  • 1 Belmont - Lounge/Bar that seats 50
  • 1 Belmont - Outdoor Dining that seats 100
Lake Front dining is provided at both of our locations - Monroe and Belmont - with indoor and outdoor options.

Job Details

Date Posted

9/2/2026

Job Title

Director of Membership Development & Engagement

Job Description

Essential Responsibilities

Membership Development

  • Develop and implement annual strategies for membership recruitment, referral cultivation, retention, and engagement.
  • Serve as the primary Club contact for prospective members, guiding them through the inquiry, tour, application, sponsorship, interview, approval, and onboarding process.
  • Conduct personalized Club tours and membership presentations that communicate the Club’s history, culture, amenities, programs, and value proposition.
  • Build and maintain a qualified prospect pipeline through member referrals, community relationships, sailing and boating networks, events, and other appropriate outreach.
  • Maintain accurate, confidential membership and prospect records in the Club’s database or CRM system.
  • Prepare membership applications, candidate materials, reports, and correspondence for the Membership Committee, Board, and General Manager.
  • Monitor membership composition, attrition, transfers, resignations, waitlists, and category utilization; recommend initiatives that support the Club’s long-term membership objectives.
  • Assist with membership forecasting, dues and initiation-fee analysis, budgeting, and annual membership plans.

Member Engagement and Retention

  • Serve as a highly visible and accessible ambassador for the Club, fostering relationships across membership categories, generations, and areas of member interest.
  • Develop and oversee new-member welcome, orientation, and integration programs that help members quickly establish meaningful connections within the Club.
  • Collaborate with Club departments to create engagement opportunities that encourage participation in sailing, boating, dining, social events, youth and family programming, committees, and member traditions.
  • Develop initiatives that recognize member milestones, accomplishments, life events, and contributions to the Club community.
  • Identify members who may be disengaged or at risk of resigning and implement appropriate outreach and retention efforts.
  • Gather, document, and evaluate member feedback through personal interaction, surveys, focus groups, event feedback, and other channels.
  • Serve as a liaison between members and Club management, ensuring concerns, suggestions, and service-recovery opportunities are handled with discretion, professionalism, and follow-through.
  • Partner with the Events, Food & Beverage, SailingOn the Water, Communications, and Facilities teams to ensure member feedback informs programming and service improvements.

Communications and Administration

  • Lead membership-related communications, including candidate correspondence, welcome materials, renewal communications, member notices, newsletters, directories, and digital content, in coordination with Club leadership and communications staff.
  • Maintain accurate member profiles, contact information, household details, membership category information, committee participation, and engagement history.
  • Ensure membership files, applications, agreements, and related records are handled confidentially and in accordance with Club policy and applicable requirements.
  • Support the development and ongoing improvement of the member directory, Club app, website membership content, and other member-facing platforms.
  • Prepare monthly and quarterly reports on membership activity, prospect pipeline, conversions, retention, participation, feedback trends, and other key performance indicators.
  • Develop and manage the departmental budget, including membership marketing, orientation, engagement programming, printing, database tools, and related expenses.
  • Attend appropriate Board, Membership Committee, and other Club committee meetings; provide staff support, reports, and recommendations as requested.

Private-club membership roles commonly include membership applications and onboarding, communications, database management, member feedback, program development, and reporting to Club leadership.

Candidate Qualifications

  • Bachelor’s degree preferred, with concentration in hospitality management, communications, marketing, business, or a related field.
  • Five or more years of progressively responsible experience in private-club membership, hospitality, member relations, business development, sales, events, or customer experience.
  • Private-club, yacht-club, country-club, hospitality, luxury service, or membership-organization experience strongly preferred.
  • Demonstrated success in relationship-building, membership recruitment, retention, service recovery, and member engagement.
  • Excellent written, verbal, presentation, and interpersonal communication skills.
  • Strong judgment, discretion, diplomacy, and ability to manage sensitive member matters confidentially.
  • Experience using CRM, membership-management, event-registration, and communication platforms.
  • Strong organizational, analytical, and project-management skills, with the ability to manage multiple priorities and deadlines.
  • Proficiency with Microsoft Office and comfort preparing reports, presentations, correspondence, and data analysis.
  • Availability to work a flexible schedule, including selected evenings, weekends, holidays, and Club events.

Educational Requirements

Date Position Available

September 1, 2026

Salary Range

$85,000.00 to $94,999.00

Other Benefits

Annual incentive target: 20%-25% of base salary

Total Compensation: $100,000-$120,000

Benefits: Medical, dental, retirement plan/match, paid time off, Club dining or meal benefit, professional development, and parking/transit as applicable.

Please send resumes to:

Keith L Brennan
General Manager
400 E Monroe St
Chicago, IL 60603
PHONE: 312-861-7760
brennan@chicagoyachtclub.org

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