Chief Development Officer

Heading Home's mission is to end homelessness in Greater Boston by providing a supported pathway to self-sufficiency that begins with a home, together with critical services such as life skills, financial literacy, and job training.

Founded in 1974, Heading Home is a leading provider of housing and support services for extremely low-income individuals and families currently or formerly experiencing homelessness in Greater Boston. For nearly 50 years, we have successfully helped thousands of people end their homelessness.

As an agency, our services are diverse; we provide emergency, transitional, and permanent housing, and support services, to extremely low-income individuals and families currently or formerly experiencing homelessness.

We are proud to share that for 16 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: Chief Development Officer

Reports To : CEO

Location: Boston, MA

Position Type : Full Time, Salary Exempt

Salary Range: $205,000 - $215,000

Hiring Timeline: June 2026

Overview:

The Chief Development Officer (CDO), reporting to the CEO, will serve as a key senior leadership team member alongside the COO and CIAO, helping to direct organizational strategy. The CDO is responsible for developing a yearly fundraising plan that includes meeting annual revenue goals via major donor/corporate support, events, foundations and the annual campaign. This position will build on existing success and donor loyalty to scale funding, expand and diversify the donor base/pipeline, and work closely with other team members to secure funding for current and new initiatives. It is expected that revenue raised by Heading Home will increase year-over-year as the CDO systematically and effectively continues to strengthen the organization’s overall fundraising capacity.

The CDO is responsible for overseeing the Development team, and all external engagement including donor relations, gift operations, marketing and communications, and volunteer engagements. The CDO will maintain a personal portfolio of major donors, oversee all organization-wide brand-related efforts, including public relations, and serve as a strategic partner to the CEO by proactively managing information flow, priorities, and preparation related to fundraising and external relationships.

In close collaboration with the CEO, the CDO will prepare, brief, and support the CEO for donor meetings, cultivation strategies, solicitations, and stewardship, ensuring the CEO is positioned for success with clear objectives, background materials, messaging, and follow-up plans. The CDO will also support the CEO in board liaison work and donor-facing communications.

Alongside revenue growth, the CDO is responsible for setting, managing and adhering to an annual department budget as well as making recommendations for high-revenue generating programs, as needed.

Responsibilities:

Fundraising Strategy and Execution:

• Create an annual revenue plan and long-term growth strategy based on strategic analysis, forecasting, and modeling that aligns with strategic goals and meets or exceeds our annual budget
• Act as chief fundraiser, deepening current donor gifts and building multi-level enterprise relationships with corporate partners to grow our Leadership Circle ($50k+) and secure multi-year funding commitments
• Partner closely with the CEO on major donor strategy, including identifying opportunities, setting meeting goals, determining solicitation roles, and developing customized engagement approaches
• Prepare the CEO for donor meetings and events by developing concise briefings, talking points, donor histories, strategic recommendations, and post-meeting follow-up plans
• Provide Development updates at all Board of Directors meetings, and work closely with the board on their giving and fundraising strategies; solicit feedback and leverage networks to advance HH’s development strategy
• Work closely with the Development Committee Chair to seek the committee’s thought leadership on department initiatives
• Set strategy and oversee Heading Home’s donor-facing events, including Housewarming (annual gala) and Changemakers (annual appreciation), and

Leadership:

• Contribute to the development and execution of HH’s organizational strategy as an integral member of the senior leadership team
• Demonstrate strong “managing up” skills by anticipating the CEO’s needs, elevating key decisions, flagging risks and opportunities, and ensuring alignment between development strategy and executive priorities
• Oversee a team responsible for major gifts, donor operations, marketing and communications, social media, grants, and volunteer engagement
• Reinforce the team’s donor-centric culture that is grounded in collaboration, trust, intentionality, and responsiveness
• Manage the department's budget and effectively communicate and hold team members accountable to budget parameters
• Set clear benchmarks for the team, regularly assess progress through data tracking and analysis, and adjust tactics as necessary to meet revenue goals
• Collaborate with the finance team on audit process, restricted revenue, pledge receivables, budgeting, and donor reporting

As leader of the Development team, oversee the department’s responsibilities to:

• Ensure data integrity, gift processing accuracy, and reliable RENXT recordkeeping
• Remain current on funding sources and trends to proactively position Heading Home for shifts in the fundraising landscape
• Implement a robust stewardship program designed to deepen donor engagement and retention.
• Create efficient and effective Development Operations processes to ensure accuracy and timeliness
• Host 1,000+ volunteers annually as part of broader cultivation and engagement strategies
• Raise awareness and brand recognition through integrated marketing efforts, including website, social media, newsletters, annual report, collateral, and earned media
• Manage external consultants and vendors supporting external relations
• Collaborate with program, real estate, and data teams to source and elevate client progress and impact data
• Maintain consistent mission-aligned messaging across all external platforms

Requirements

• 10+ years of professional experience with a successful track record in non-profit fundraising across a variety of revenue streams.
• Experience in closing multi-year commitments and catalyst gifts at the $100K+ level
• Demonstrated success creating and executing strategic development plans that expand and deepen donor relationships
• Strong strategic, critical and reflective thinking with the ability to make data- informed decisions
• Proven people manager with experience building, leading, and developing high-performing teams
• Experience working closely with executive leadership and cross-functional teams.
• Experience leading or collaborating with a Board of Directors
• Demonstrated ability to manage up effectively, partner with executive leadership, and prepare senior leaders for high-stakes donor engagement
• Flexible adaptable leadership style with the ability to operate at both strategic and tactical levels
• Excellent written and verbal communication skills
• Strong organizational and time management skills with exceptional attention to detail
• Ability to balance multiple priorities while driving both short- and long-term results
• Deep alignment with Heading Home’s mission and commitment to diversity, equity, and inclusion
• Bachelor’s degree required, Master’s preferred

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.