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Job Title: Director of Development

Reports To: Executive Director
Status: Full-time 

Position Summary

Courageous Sailing Center is a not for 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.  Over 1,000 youth and 350 adults are served annually.

Reporting to the Executive Director, the Director of Development (D.o.D.)will be responsible for all fundraising campaigns, events, annual fund activities and communications with donors, foundations, sponsors and stakeholders.  S/he will lead and coordinate fundraising and communications programming with the intent of engaging, diversifying and growing the base of Courageous donors. 

The D.o.D. position demands a person of innate leadership abilities; a strategist; a strong and comfortable communicator; one with demonstrated organizational skills; a person who can operate comfortably in a variety of milieus from a donor’s living room to the boardroom of a large foundation or of a major corporation; an individual marked by initiative, creative energy – who can make the ask and close the gift; a team player – dependable, hard-working and inspiring. The candidate must be passionate for the mission of Courageous Sailing.

The successful candidate will:

  • Raise funds:The key metric of success will be money raised.
  • Establish and execute a fundraising plan and processes that foster a pattern of giving (through sponsorships, donations and grants) that is diversified and reliable over time.
  • Build relationships, with donors, corporations, grantmaking institutions and community stakeholders.

To apply, please send a cover letter and resume, via email, to:  jobs@courageoussailing.org


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

  • Strategize and design a diversified, high-impact annual development plan designed to support an annual budget of $1.4M.  Set annual, quantifiable goals and review set goals regularly.
  • Lead and manage implementation of all annual fund, foundation, corporate and event strategies and activities.
  • Oversee major donor, foundation and sponsor identification, solicitation and stewardship.  Create and maintain a targeted list of prospective grant making institutions, individual donors, corporate sponsors and other funding opportunities. Ensure all communication with donors is well organized and managed.
  • Develop strategy and content for donor-focused inbound marketing and social media.
  • Identify and mentor all fundraising teams (E.D., staff, volunteers, Board and committees) to achieve or exceed annual agreed upon goals.
  • Research, write and submit proposals for grant opportunities.
  • Plan, manage and leverage fundraising events.
  • Produce high quality reports to individual donors and foundation/corporate funders; including case statements for funding priorities; ensure that active donors receive updates or communications from Courageous once per quarter. Focus on strategically developing communications materials that will encourage donors to re-engage with Courageous.
  • Develop and manage donor acknowledgement and recognition programs. Ensure that as each gift is made proper recognition and thanks are conveyed. Create acknowledgment letter templates and update them on an as needed basis.
  • Develop naming and sponsorship opportunities that match donor interests.
  • Build relationships with community groups and other key constituents.
  • Oversee and cultivate a development database to facilitate informed and strategic contact with donors, foundations, corporations, and individuals.
  • Working in close collaboration with the E.D., the D.o.D.will support all Board development activities including:
    • Collaborate with the Board when designing and reviewing annual, major donor and campaign fund development partnerships and strategies.
    • Create and maintain all the materials that board, partners, and others need to tell the Courageous story in a compelling fashion.
    • Support the Board by helping them define their own philanthropic goals and strategies as well as setting and fulfilling their goals re: the identification of prospects from their personal and professional networks.
    • Oversee Board stewardship initiatives and support the identification, recruitment, orientation and cultivation of prospective Board members.


  • 4 – 6+ years of professional experience in a not for profit organization; demonstrated success in forging, managing and expanding relationships with individual donors, grant-making foundations and corporate sponsors.  Proven, successful experience in identifying, securing, maintaining and stewarding donors.  The successful candidate should have experience in working with donors of gifts from $1,000 - $100,000+.
  • Excellent communication skills, both written and verbal; ability to influence and engage a wide range of donors and build long-term relationships with diverse constituencies.
  • Ability to construct, articulate and implement annual strategic development plan.
  • Strong organizational and time management skills with exceptional attention to detail.
  • Ability to work both independently without close oversight, but also a team player who will productively engage with others at varying levels of seniority within and outside CS
  • High energy and passion for CS’s mission.
  • Computer literacy including proficiency in Microsoft Word, Excel and Powerpoint expected - development/fundraising database programs a plus.
  • Bachelor’s degree in Communications, Public Relations, Marketing or other equivalent fields.

Salary & Benefits

Salary commensurate with experience.  Benefits include health, dental and IRA.

Courageous Sailing is an equal opportunity employer and 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.

Job Description

The Assistant Adult Program Director is one of the most important seasonal positions at Courageous Sailing. As the person behind our Front Desk, s/he is often the face of the organization, serving as the first point of contact for the public, either personally or over the phone.  S/he is a primary resource for our students and members, and must be friendly, polite, and knowledgeable of the operations and rules of Courageous.

 The Assistant Adult Program Director undertakes daily administrative tasks and generally assists the Adult Program Director with operations tasks. These duties range from fielding questions about our courses, memberships, and ratings systems to managing the daily flow of people and boats through the program. The Assistant Adult Program Director also monitors staff radio use, marine traffic, weather, and wind.  S/he must be highly organized, have great people skills, and be able to multi-task in a sometimes hectic, fast-paced environment. Sailing experience and the ability to explain sailing skills and requirements are strongly preferred.



The Assistant Adult Program Director position is a full time, summer seasonal position with hours tapering off in October.  Season ends October 31st.   Candidates must be able to work weekends, and some days or evenings during the week.  

Minimum qualifications include:

·         Excellent communication and interpersonal skills.

·         Ability to work independently, multi-task, prioritize responsibilities, take initiative, and appropriately handle confidential information.

·         Comfortable working under pressure, exercising strong problem-solving skills, and willing to adapt to changing program needs.

·         Skilled at monitoring and managing multiple information feeds simultaneously.

·         Attention to detail and commitment to accuracy.

·         Familiarity with basic computer systems and social networking programs.

·         Ability to quickly and enthusiastically master additional technology, skills, & knowledge as needed.

·         Sailing knowledge and skills preferred but not required.


About Courageous Sailing

Courageous Sailing is a non-profit community sailing center committed to providing access to the sport of sailing through our sailing school and membership programs.  Sailing is a tremendous platform for education, personal growth and leadership development, and we are dedicated to making the highest quality sailing education available to the entire Boston community regardless of socio-economic background, ethnicity, or ability.  Our youth and adult programs promote a culture of responsibility, respect, and stewardship around sailing on Boston Harbor, and foster life-long learning opportunities for all members of our community.  We rely on a team of passionate, hard-working individuals to provide top level instruction, attentive customer service, and, above all, a safe and welcoming environment.



Compensation can be adjusted for experienced candidates, but will be in the range of $15 per hour.


To Apply

To apply for this position, please send an email with subject line “Assistant Adult Program Director Application” with resume and cover letter to bryan@courageoussailing.org

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