• Fall is the perfect time to experience Boston Harbor, and Courageous Sailing is offering special deals for Charlestown residents. Summer vacation doesn’t need to be over.
  • 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/Business Manager

Reports To: Executive Director
FLSA Status: Non-exempt
Status: Full-time
Date of Last Revision: September 2016

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/Business Manager takes 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. The Office/Business Manager operates on a broad spectrum with major tasks including oversight of the essential business functions of the organization, including bookkeeping, human resources, technology, events and general administration. A true team player, the Office/Business Manager is involved with 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 possess an excellent work ethic, organizational skills, and capacity for multitasking; experience with database, accounting and spreadsheet software; exemplary communication and writing skills; and the maturity to responsibly handle sensitive information and situations.


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

  1. Information Management
    1. Maintaining our donor and constituent database and coordinating the use of the system by program staff
    2. Administering cloud-based resources such as Google Apps, Dropbox, Smartsheet and Asana
    3. Updating office technology as needed, including both hardware and software
  2. Bookkeeping
    1. Working directly with accountant, Board Treasurer and ED to ensure appropriate financial controls and oversight
    2. Tracking, processing, and depositing all incoming and outgoing monies
    3. Assisting with cash flow tracking, financial reconciliations, and reporting
    4. Assisting with budget planning
  3. 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
  4. Administrative
    1. 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
    2. Ordering office supplies and merchandise as needed
  5. Events
    1. Conducting site reviews and building relationships with event planners and caterers in the area
    2. Acting as a contact for all pier rental inquiries and helping to track and schedule all events
    3. Overseeing the logistics of fundraising events, including organizing sponsorships and auction catalogs, set-up, day-of coordination, and staff management, as well as tracking attendance, ticket sales, donations, and receipt of any auction or raffle winnings
    4. Working with City Hall to obtain all seasonal and one-day event licenses 

Qualifications / Skills

  1. Excellent organizational skills and attention to detail
  2. Excellent communication and interpersonal skills
  3. Fluency with Salesforce or similar database; Microsoft Office, especially Excel; and social media
  4. Familiarity with Quickbooks or equivalent or basic accounting practices
  5. Ease in managing multiple projects simultaneously, working independently and under a deadline, prioritizing responsibilities, taking initiative, and appropriately handling confidential information
  6. Bachelors Degree
  7. 1-3 Years office management experience 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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