Senior Director of Development

Job Title: Senior Director of Development 

Reports To: CEO 

Location: Boston, MA; 4 days in office; 1-day remote 

Position Type: Full-Time, Salary Exempt 

Annual Salary: $145,000 - $160,000 

Overview:

The Senior Director of Development 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 works closely with the CEO to develop and execute 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 CEO, Board members, and Development team, the Senior Director of Development will develop a plan to expand Heading Home's major gifts program while strengthening relationships with our most significant supporters.

Key Responsibilities:

Major Gift Fundraising 

• Responsible for raising at least $3M of a $6M fundraising budget. 
• Maintain an active pipeline in qualified opportunities to assist in getting to the fundraising goal. 
• Build and actively manage a portfolio of major gift prospects and donors. 
• Develop individualized cultivation, solicitation, and stewardship strategies for each assigned donor. 
• Conduct discovery meetings to identify donor interests, philanthropic priorities, and giving capacity. 
• Personally solicit and close five-, six-, and seven-figure gifts. 
• Maintain regular communication with assigned donors through meetings, calls, correspondence, and program updates. 

Business Development 

• Identify, qualify, and cultivate new major gift prospects throughout Massachusetts and beyond. 
• Develop relationships with leaders in financial services, healthcare, technology, life sciences, professional services, family foundations, and private philanthropy. 
• Partner with Board members, volunteers, corporate partners, and community leaders to expand Heading
• Home's philanthropic network. 
• Convert event attendees, volunteers, sponsors, and community partners into long-term individual donors. 

Donor Engagement & Stewardship 

• Coordinate donor visits to Heading Home programs sites. 
• 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. 

Event Management 

• Oversee the development and execution of Heading Home’s two key events, Housewarming and Changemakers. 
• Work closely with the CEO to motivate and engage the board and donor volunteer to meet the $3M
• Housewarming event goal. 
• Manage the event vendor relationships to ensure smooth execution. 

Supervision and Management 

• Supervise, mentor, and develop the Grants Manager, Operations Development Associate, Volunteer Development Associate and Development Officer. 
• Set team goals, monitor performance, and ensure accountability for fundraising and engagement objectives. 
• Oversee daily development operations, ensuring timely execution of grants, donor stewardship, gift processing, and volunteer initiatives. 
• Foster collaboration across the development team and with internal departments to support organizational fundraising goals. 
• Build a high-performing, mission-driven team focused on continuous improvement and exceptional donor service. 

Data Management & Reporting 

• Oversee the maintenance of accurate donor records, activity tracking, and moves management documentation within Raiser's Edge NXT. 
• Monitor portfolio performance, donor pipeline activity, proposal success rates, and fundraising revenue. 
• Prepare monthly reports and revenue forecasts for the CEO. 
• Ensure all donor interactions and next steps are documented in accordance with Development Department standards. 

Requirements:

• Bachelor's degree required. 
• Seven 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. 

Equal Employment Opportunity Statement 

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. 

Work Environment 

Normal for an office work environment.