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

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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• Bachelor's degree required.
• Seven or more years of frontline major…