Managing Director

Accepting RFPs until June 9, 2023

Job Description



Cover letter: Please include the RFP subject and name of proposer with all applicable contact information, and date of preparation.

Qualifications:  Describe the background, experience, and capabilities of the proposer as it relates to the Scope of Work outlined above. Highlight any successful work performed in other leagues, non-profit organizations, or community service organizations during the last five years.

Scope of Services: Provide a scope of services and a proposed outline of tasks, products, and schedules. Also, identify the extent of CMSA personnel involvement deemed necessary, including key decision points at each stage of the project. Major proposed deviations from the desired scope of services outlined above should be clearly noted and justified.

Cost: Provide cost proposal for scope of services including fixed costs, fees, expenses, reimbursable costs, and any other anticipated costs.

References: Provide a list of at least three clients the proposer has contracted or worked with in the past three years who can verify proposer’s ability to provide the Scope of Work. Provide name, title, workplace, email, and phone number. Provide a list of current clients or organizations, if any who are receiving services like those requested in this RFP with a brief description of the work.

Additional Services:  The selected proposer is welcome to outline additional services or alternative approaches that it feels are in the best interest of CMSA.

PROPOSAL SUBMISSION:  The deadline for submission is June 9, 2023 at 5:00 p.m. CST. Proposals will only be accepted via email and in PDF form. The proposer must submit one (1) signed electronic PDF version of the proposal by the deadline to Steve Leaver at


MANAGING DIRECTOR: Chicago Metropolitan Sports Association (CMSA) invites qualified operational leaders and consultants to submit a written proposal to serve as the Association’s Managing Director.


ELIGIBILITY:  To be eligible for consideration, the proposer must demonstrate that he/she/they have successfully performed similar services to those specified in the Scope of Work section of this RFP, with institutions similar in size and complexity to CMSA. The successful proposer will work directly with CMSA’s Board of Directors, and any other CMSA representative selected to be involved with activities associated with this project.


The Chicago Metropolitan Sports Association (CMSA) is the largest non-for-profit LGBTQ+ sports organization in the Midwest. We offer recreational and competitive level play in a variety of athletic leagues throughout the year. The league is open to all persons who wish to play, regardless of sexual orientation, gender or gender identity.

Chicago Metropolitan Sports Association (CMSA) is looking to hire a Managing Director to oversee the operations of the organization.


The Managing Director reports directly to the Board of Directors. The Managing Director will function as the main point of contact for all League Commissioners, vendors, and members of CMSA.



  • Work with bookkeeper to maintain QuickBooks
  • Create financial reports for the board
  • Collaborate with Board Treasurer and League Commissioners on the creation and oversight of League budgets
  • Assist and oversee the audit process and file appropriate tax documents
  • Maintain rigorous financial controls for the protection of the league’s resources against fraud, theft and misuse



  • Maintain proper insurance across the leagues
  • Secure Park district contracts with Chicago Park District
  • Facilitate and maintain online presence through League Apps, website, social media
  • Create and distribute monthly league newsletter consistently and timely
  • Assist with board transition and orientation of new board members
  • Maintain good standing as a non-profit 501©3 tax-exempt organization


Strategic Planning

  • Partner with the Board of Directors with continued development and maintenance of the CMSA strategic plan


Sponsorships and Fundraising

  • Secure and maintain relationships with vendors
  • Collaborate with Board of Directors, Commissioners, and community members to identify fundraising opportunities


Areas of Experience


  • QuickBooks Online
  • Direct management of bookkeeping vendor
  • Budget review and management



  • Social Media Management including content creation and distribution
  • Event Planning
  • Organization (internal and extra) Communications

Managing Director Qualifications / Skills:

  • Demonstrable leadership and management skills
  • Proficient with Google Suite of applications, and other basic organizational computer programs
  • Intuitive: Takes initiative
  • Confident working independently and collaboratively and in a team environment
  • Creative problem-solving skills
  • Enthusiastic
  • Organized

Education and Experience

  • Bachelor’s Degree or relevant experience
  • Non-profit experience in an operational environment
  • Sports management experience a plus
  • Familiarity with the LGBTQ+ community a plus