• Explore. Learn. Sail! Low-cost, high-quality programs that connect city youth with Boston Harbor and Jamaica Pond. Summer Youth Sailing Program
  • Convenient and affordable courses, lessons, and memberships for all experience levels and interests. Sailing for Adults + Families
  • Work for Courageous

    Love sailing? Love teaching? Courageous is currently hiring for a variety of seasonal and summer jobs for our youth and adult programs. Spend your summer sailing with kids, teach sailing to adults on weekends, or help run one of our programs! Read More
  • Summer Youth Program Registration

    Registration is now closed. View the FAQ to learn what to do if your child was registered successfully or put on the waiting list. The FAQ also details the 2016 fees and scholarships. Read More
  • Sail Boston Harbor!

    At Courageous, we’re committed to providing some of the best and most affordable sailing opportunities on Boston Harbor for adults and families. Whether you’re a total beginner or an expert sailor, we’ve got a course or membership to fit your needs and interests. Read More

Office Manager

Reports To: Executive Director
FLSA Status: Non-exempt
Status: Part-time
Date of Last Revision: September 2013

Position Summary

Courageous Sailing, a 501(c)3 nonprofit engaged in sailing education for Boston youth, seeks a high energy office manager to keep the wheels turning at our boat house on Pier 4 in the Charlestown Navy Yard. Bookkeeping, HR and payroll processing, organizational management, and regular communication with staff and board members comprise the basic requirements of this position. Working alongside a committed staff, the well-organized, detail-oriented self-starter has the opportunity to transform these abilities into specific transferable job skills within a supportive, fast-paced work environment.

Reporting to the Executive Director, the Office Manager operates independently to take primary responsibility for managing the non-programmatic aspects of the organization. This position is fundamental to the organization’s ability to operate smoothly and economically. Major tasks include bookkeeping, processing payroll, general office administration and correspondence, and acting as the recording secretary for the Board of Directors. A true team player, the Office Manager plays a role in many aspects of the organization and works closely with the Executive Director to assist in both daily and big picture operations.

The ideal candidate will arrive on the pier with an excellent work ethic, organizational skills, and capacity for multitasking; experience with accounting and spreadsheet software; exemplary communication and writing skills; and the maturity to responsibly handle sensitive information and situations. This is a part-time year round position with peak workload in the spring and summer months. Compensation range:  $18-22/hour, based on skills and experience.



These include, but are not necessarily limited to, the following:

  1. Bookkeeping
    1. Tracking, processing, and depositing all incoming and outgoing monies
    2. Handling all routine bookkeeping
    3. Acting as the point of contact for the volunteer Treasurer, tracking cash flow, providing financial reconciliation and reporting
    4. Assisting with budget planning
  2. Human Resources
    1. Maintaining all payroll records and managing the timely submission of payroll reports 
    2. Processing all hiring documents, including CORI and SORI requests 
    3. Tracking and updating insurance plans, payments, and renewals in conjunction with our broker
    4. Managing benefits for staff members
  3. Administrative
    1. Managing relationships with and payments to all vendors 
    2. Keeping updated records of all current contracts for reference and acting as a liaison on behalf of Courageous and staff to organize contractual agreements and/or renewals 
    3. Working with City Hall to obtain all seasonal and one-day event licenses for operations and events
    4. Updating office technology as needed, including both hardware and software
    5. Serving as the first point of contact with the public by answering and directing phone calls, fielding questions, and explaining Courageous programing
    6. Helping Program Directors with program administration, general organization, and extra staffing, as time permits.
    7. Assisting Executive Director and management team with the fundraising events, as time permits.


The Office Manager position requires a high level of proficiency in bookkeeping and office administration.

Minimum qualifications include:

  1. Excellent communication, writing, and interpersonal skills
  2. Ability to work independently, multi-task, prioritize responsibilities, take initiative, organize on-line and paper records, and appropriately handle confidential information
  3. Comfortable working under a deadline
  4. Skilled at managing multiple projects simultaneously, with attention to detail and commitment to accuracy
  5. Demonstrably strong skill with Microsoft Office, especially Excel
  6. Experience MYOB, Quickbooks or equivalent, and basic accounting practices
  7. Understanding of fundamental good business practices
  8. Associates Degree required, Bachelor’s Degree preferred

About Courageous

Courageous Sailing is a non-profit sailing center dedicated to transforming the lives of underserved populations of youth through sailing.  The program has been in continuous operation since 1987 and is based in the Charlestown Navy Yard on Boston Harbor.  The youth program is supported by the operation of the adult program, grants, corporate sponsorships, individual donations and fundraising events. 

COURAGEOUS SAILING is an Equal Opportunity Employer.

Courageous Sailing does not discriminate in employment on the basis of race, color, religion, sex, sexual orientation, national origin, age, genetic, disability or veteran/Reserve/National Guard status.

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Find Us

Pier 4, Charlestown Navy Yard, Boston, MA 02129



Courageous Mainsail Partners


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