Heading Home's mission is to prevent and end homelessness. Through personalized support and shelter, as well as larger advocacy and affordable housing work, we provide stability and foster the independence every family and individual needs to thrive.
Founded in 1974, Heading Home is a leading provider of housing and support services for low and extremely low-income individuals and families currently or formerly experiencing homelessness in Eastern Massachusetts. For over 50 years, we have successfully helped thousands of people end their homelessness.
As an agency, our services are diverse; we provide emergency, transitional, permanent and affordable housing, and support services, to low-income individuals and families.
We are proud to share that for 17 years running, Heading Home's permanent housing retention rates have been 90%+. Last year, 97% of Heading Home clients remained housed after one year.
Job Title: Director of Major Gifts
Reports To: CDO
Location: Boston, MA; 4 days in office; 1 day remote
Position Type: Full-Time, Salary Exempt
Annual Salary: $90,000 - $108,000
Overview:
The Director of Major Gifts serves as Heading Home's lead frontline fundraiser, responsible for building meaningful relationships with individual philanthropists who are passionate about preventing and ending homelessness. This position develops and executes strategies to identify, cultivate, solicit, and steward major donors whose investments advance Heading Home's mission and long-term strategic priorities.
This role requires a highly relationship-driven fundraising professional with a proven ability to secure transformational gifts, develop new philanthropic partnerships, and inspire donors through compelling storytelling and measurable impact. Working closely with the Chief Development Officer, CEO, Board members, and Development team, the Director of Major Gifts will expand Heading Home's major gifts program while strengthening relationships with our most significant supporters.
Key Responsibilities
Major Gift Fundraising
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Raise $1.5M of a $6M fundraising budget.
- Maintain an active pipeline of approximately $4 million in qualified opportunities.
- Build and actively manage a portfolio of approximately 125–150 major gift prospects and donors.
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Develop individualized cultivation, solicitation, and stewardship strategies for each assigned donor.
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Conduct discovery meetings to identify donor interests, philanthropic priorities, and giving capacity.
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Personally solicit and close five-, six-, and seven-figure gifts.
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Prepare customized gift proposals, investment opportunities, stewardship reports, and impact presentations.
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Ensure thoughtful stewardship and recognition to encourage continued investment and long-term donor retention.
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Maintain regular communication with assigned donors through meetings, calls, correspondence, and program updates.
Business Development
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Identify, qualify, and cultivate new major gift prospects throughout Massachusetts and beyond.
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Develop relationships with leaders in financial services, healthcare, technology, life sciences, professional services, family foundations, and private philanthropy.
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Partner with Board members, volunteers, corporate partners, and community leaders to expand Heading Home's philanthropic network.
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Convert event attendees, volunteers, sponsors, and community partners into long-term individual donors.
Donor Engagement & Stewardship
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Coordinate donor visits to Heading Home programs sites.
- Partner with the Development team to create meaningful donor engagement opportunities, including CEO briefings, volunteer experiences, cultivation events, and special initiatives.
- Develop stewardship strategies that demonstrate donor impact and strengthen long-term relationships.
- Work with Marketing & Communications to share compelling stories of mission impact with donors.
Development Strategy & Collaboration
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Work closely with the Chief Development Officer to establish annual fundraising goals and major gift strategies.
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Partner with the Development Operations Director to identify funding opportunities and maximize donor engagement.
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Collaborate with the Donor Stewardship Manager to leverage organizational events and volunteer opportunities for donor cultivation.
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Serve as a strategic fundraising partner to the CEO and volunteer leadership.
Data Management & Reporting
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Maintain complete and accurate donor records, activity tracking, and moves management documentation within Raiser's Edge NXT.
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Monitor portfolio performance, donor pipeline activity, proposal success rates, and fundraising revenue.
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Prepare monthly reports and revenue forecasts for the Chief Development Officer.
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Ensure all donor interactions and next steps are documented in accordance with Development Department standards.
Heading Home, Inc. is an Equal Employment Opportunity (EEO) employer and welcomes all qualified applicants. Applicants will receive fair and impartial consideration without regard to race, sex, color, national origin, age, disability, veteran status, genetic data, gender identity, sexual orientation, religion or other legally protected status, or any other classification protected by federal, state, or local law.
Normal for an office work environment.
Qualifications
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Bachelor's degree required.
- Five or more years of frontline major gift fundraising experience.
- Demonstrated success securing five- and six-figure philanthropic investments.
- Proven ability to independently manage and grow a major gift portfolio.
- Experience developing customized donor strategies and complex gift solicitations.
- Excellent written, verbal, and presentation skills.
- Experience with Blackbaud Raiser's Edge NXT or comparable donor CRM.
- Strong organizational and project management skills with exceptional attention to detail.
- Ability to manage multiple priorities while meeting deadlines.
- Self-starter who works independently while collaborating effectively across teams.
- Ability to handle confidential donor information with discretion.
- Willingness to work occasional evenings and weekends for donor meetings and special events.
- Passion for Heading Home's mission and commitment to equitable housing and ending homelessness.
