Description

SailMaine is a 501(c)3 nonprofit community sailing center based on the working waterfront of Portland, Maine, with a commitment to providing affordable and inclusive access to sailing and the waters of Maine since 1996. Our mission is to foster an inclusive community, cultivate personal growth, and inspire a love of sailing through affordable access to the waters of Maine. SailMaine serves people of all ages, with a special focus on youth, and removes barriers to participation through community partnerships, scholarships, and free community access programs.

SailMaine’s youth and adult learn-to-sail, boat rental, and racing programs are equally strong and serve as a vital source of community engagement, volunteerism, and philanthropic support. Supported by strong involvement from its executive Board of Directors, SailMaine recently completed a successful $250,000 campaign to purchase a fleet of J22 sailboats for launch in 2026 in celebration of our 30th anniversary.

Position Summary
SailMaine seeks an experienced, strategic, and relationship-driven Development Director to lead and grow the organization’s fundraising program during a period of expansion and long-term planning. Building on a strong 30-year foundation and recent fundraising momentum, the Development Director will strengthen annual philanthropy, expand major and leadership giving, deepen foundation partnerships, and position SailMaine for future capital initiatives, including long-term plans for a waterfront facility.

This senior leadership role is responsible for designing and executing a comprehensive, multi-year fundraising strategy aligned with SailMaine’s mission and strategic plan. The Development Director will personally manage a portfolio of leadership and major gift prospects, partnering with the Executive Director and Board members to cultivate, solicit, and steward donors.

The Director will supervise one development team member, collaborate closely with senior leadership on communications and strategic initiatives, and build systems that ensure long-term financial sustainability and growth.

Key Responsibilities

Strategy & Leadership

• Develop and implement a comprehensive, multi-year fundraising strategy aligned with SailMaine’s mission, strategic plan, and growth goals
• Build and lead annual fundraising budget and plan, including individual giving, major gifts, foundations, grants, events, and periodic campaigns
• Personally manage a portfolio of major and leadership gift prospects, across the full advancement cycle comprising identification, cultivation, solicitation, and stewardship
• Establish fundraising metrics and regularly report progress to the Executive Director and Board of Directors
• Supervise and support development staff and consultants
• Program & Impact Fundraising
• Partner with leadership team to articulate impact and develop case for support
• Secure philanthropic support for youth access programs, community sailing, scholarships, and annual infrastructure needs
• Strengthen donor communications and storytelling in collaboration with leadership team
• Oversee annual fundraising events in partnership with the Board of Directors, development staff, and volunteers 

Systems Management

• Strengthen fundraising processes, including strategic development of existing CRM platform, supported by prospect and donor data management and research
• Oversee grant and foundation annual cycles and stewardship process
• Ensure timely, consistent, and professional direct mail campaigns, digital campaigns, other donor communications, and donor acknowledgements

Board & Leadership Engagement

• Partner with the Executive Director to engage and activate the Board of Directors in fundraising leadership and donor activities
• Lead the Development Committee in partnership with the Board of Directors and provide tools and coaching to help Board members fulfill fundraising activities
• Collaborate with leadership team on organizational budgeting, forecasting, and long-term sustainability planning as well as periodic updates to the strategic plan
• Capital Readiness & Long-Term Planning
• Develop a strategic case for support focused on diversifying and shifting the mix of funding sources over the next three to five years
• Lay the groundwork for future capital fundraising, including major gift cultivation and campaign readiness
• Support long-term planning related to facilities and infrastructure that expand community access to the waterfront

Compensation
This is a permanent, full-time position with benefits including health insurance, vacation and sick time, and paid holidays. The annual starting salary range for this role is $77,000 to $90,000 commensurate with experience. SailMaine will support the Director’s professional growth. 

To apply, please email a cover letter and resume, separate PDF attachments with “Development Director” as the subject. Application review will begin on April 4 and continue until the position is filled.

SailMaine is committed to maintaining a diverse workforce and an inclusive work environment. We are committed to equal opportunity for all applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or other legally protected characteristics.

Requirements

• 5–7+ years of progressive nonprofit fundraising experience, including leadership-level responsibility
• Demonstrated success securing major and leadership gifts and managing donor portfolios
• Proven ability to design and implement comprehensive fundraising strategies across annual giving, major gifts, foundations, grants, events, and campaigns
• Experience partnering with executive leadership and working effectively with engaged Boards of Directors
• Leadership experience in managing and leading people
• Data-informed approach to decision-making and performance management
• Experience leading a team to strengthen fundraising systems and infrastructure
• Strong strategic planning, analytical, and critical thinking skills
• Excellent written and verbal communication skills, with the ability to articulate mission impact persuasively
• Experience with capital campaign readiness or campaign management preferred
• Proficiency with donor database/CRM systems and wealth screening tools
• Passion for youth development, community-building, and expanding access to the outdoors; a love of sailing or connection to the water is a plus
• Comfort working on the waterfront in a shared office space and in an environment that promotes diversity, equity, and inclusion in service of its community
• Willingness to work occasional evenings, weekends, and events