Senior Director of Major and Planned Giving

July 2022 | Hybrid/Boston, MA

Pine Street Inn seeks a Senior Director of Major and Planned Giving to lead its high performing Major and Planned Giving Program

About Pine Street Inn


Pine Street Inn opened its doors in 1969. Over more than five decades it has grown into New England’s largest nonprofit resource for homeless and formerly homeless adults. Throughout the ‘80s and ‘90s, Pine Street expanded from offering basic necessities—food, clothing, shelter, and health care—to offering programs that help guests take significant steps in their journey out of homelessness and regain some of what they have lost: relationships, life skills, employment, and housing. In the past ten years, Pine Street has significantly expanded its inventory of permanent supportive housing to provide lasting solutions to homelessness. 

Mission: Pine Street Inn partners with homeless individuals to help them move from the streets and shelter to a home and assists formerly homeless individuals in retaining housing. The Inn provides street outreach, emergency services, supportive housing, job training, and connections to employment. Pine Street tirelessly advocates for collaborative solutions to homelessness.

Pine Street’s programs include:

  • Permanent Supportive Housing – Approximately 900 formerly homeless individuals live in 35 residences and in scattered-site rental units throughout Greater Boston. The program for tenants is a supportive housing model – permanent housing coupled with on-site support staff to help each individual regain their highest level of independence. Specialized housing is available for seniors, adults with mental health disabilities, and veterans. Pine Street currently has a housing retention rate of 97%.
  • Emergency Shelter – Each night, Pine Street Inn operates four emergency shelters. Each offers a warm and safe bed, two nutritious meals, and shower and locker facilities, as well as access to health care, substance use treatment and psychiatric support. Innovative new programs such as Front-Door Triage and Rapid Rehousing are creating new paths out of Pine Street’s shelters and into the stability of housing.
  • Job Training – Pine Street provides job training in food services and housekeeping, providing individuals with the skills they need to find and keep jobs. Approximately 130 individuals are served in job training programs each year.
  • Street Outreach – Pine Street’s day and night street outreach teams travel throughout Boston to offer food, blankets, health care and access to shelter and housing to unsheltered individuals. 

Today, Pine Street Inn serves 1,400 individuals a day. From emergency services, to needs assessment, counseling and case management, to job training and placement in permanent housing, Pine Street Inn is providing short-term remedies and long-term solutions to end the experience of homelessness.

About Philanthropy at Pine Street Inn

Pine Street’s $75M annual operating budget is primarily funded through government grants and private philanthropy. Last year, Pine Street raised more than $24M, of which $15.5M was in unrestricted support. Pine Street has a robust donor community of 35,000+ and engages thousands of volunteers annually.

In addition, Pine Street Inn has recently completed its Key Moments Campaign, a $50M fundraising effort to commemorate its 50th anniversary. The campaign was launched in 2017 to create, preserve, and sustain permanent housing solutions for Boston’s most vulnerable individuals. Key Moments received support from more than 800 donors across the donor community, including many of Boston’s leading philanthropists. This campaign has expanded Pine Street’s housing initiatives, confirmed the importance of affordable supportive housing in its future work and deepened its relationships with major donors determined to end homelessness in Boston.

The Covid-19 pandemic has underscored the importance of Pine Street’s work for the safety, health, and security of guests and the entire Boston community. Pine Street quickly responded to the pandemic and implemented plans to safely serve guests in pandemic and post-pandemic environments. These plans require critical investments and have positioned the Advancement Department for bold fundraising priorities in the coming years.

About the Position

Pine-Street-Inn-mealThe Senior Director of Major and Planned Giving (SDMPG) will join Pine Street Inn as it builds upon the tremendous success of its $50 million campaign, which exceeded goal a year early and further solidified Pine Street’s nationally recognized reputation as a trailblazer in conquering homelessness. The SDMPG will build and lead a high-caliber and growing major and planned giving program that reflects Pine Street’s culture, mission, goals, and bold strategic plan.

Reporting to the Chief Advancement Officer (CAO), the SDMPG will join the Advancement senior leadership team in driving an ongoing organization-wide conversation about vision, strategy, idea generation and goals for development. An experienced, collaborative, mission-driven, and entrepreneurial leader, they will excel at frontline fundraising, developing creative and effective prospect and engagement strategies, and managing and mentoring a team. In partnership with the executive team, board members, senior leadership, staff, and volunteers, the SDMPG will grow a major and planned giving program that taps into unrealized potential from the surge in pandemic-era giving and a robust annual giving program, developing relationships with new prospects and taking relationships with existing donors to the next level to significantly grow philanthropic giving at Pine Street.

This position is eligible for a hybrid work schedule, which includes regular on-site work and local travel.

Key Responsibilities

The SDMPG serves in an important leadership role reporting directly to the CAO and will have overall responsibility for a comprehensive program that will propel Pine Street toward achieving its inspiring vision while aligning with its ethos of innovation and impact.

The SDMPG will also be an externally facing fundraiser who will:

  • Develop and lead a goal and outcome oriented major and planned giving program that enables Pine Street to fully realize its prospect potential:
    • Design and implement, with the Advancement senior leadership team, a comprehensive fundraising plan that incorporates new ideas to strategically engage the significantly expanded network of donors
    • Set ambitious and transparent revenue, performance, and engagement goals
    • Monitor progress to goal and recalibrate plan accordingly
    • Develop systems and processes, with advancement operations team, to fully leverage analytics and database capabilities to realize prospect potential
  • Manage a portfolio of approximately 75 – 100 major gift prospects and solicit and close gifts of 5, 6, 7 and 8 figures
  • Build and provide strategic leadership of the 3-person major and planned giving team:
    • Serve as an example and hands-on expert in engaging and inspiring donors to give
    • Partner in developing creative prospect strategy
    • Provide coaching and mentorship
    • Ensure effectiveness and accountability
    • Foster a collaborative and positive environment, both within the major and planned giving team and within the Advancement department writ large
  • Support and partner with the President/Executive Director, CAO and select Board members and volunteers on major fundraising initiatives
  • Collaborate with Advancement and program staff to define and articulate a sophisticated and compelling case for support
  • Partner with donor engagement and event team members to plan dynamic cultivation and stewardship opportunities that will support major gift efforts

Key Qualifications

The successful candidate will be a strategic, creative team leader who is visionary about PSI’s fundraising potential and who can support the CAO’s vision for philanthropy while maximizing team results. They will possess outstanding interpersonal competencies, and a deep commitment to instilling best practices and a culture within the Major and Planned Giving team that reflects PSI’s values.

  • 8-10 years of progressively responsible experience in a successful individual giving program with a proven track record of deepening individual relationships and securing six-to-seven-figure gifts; some experience working with non-built-in constituencies preferred
  • Strong management skills with demonstrated success in building, managing, and mentoring a highly effective and diverse team toward achieving team goals
  • Experience managing and engaging Board level volunteers
  • Commitment to the mission of Pine Street Inn
  • Strong verbal and written communication skills, presentation skills, and analytical skills
  • A metrics-driven, self-motivated, entrepreneurial mindset that informs strategy and work
  • Strong team player with a commitment to working in a collaborative environment and the ability to be flexible and tenacious
  • Openness to travel on behalf of PSI for donor visits or as the organization’s representative
  • A bachelor’s degree or equivalent experience
  • Some weekend, evening, and major holidays required

All qualified candidates will receive consideration for employment without regard to race, color, religion, sex, national origin, disability, veteran status, or any other characteristic protected by law.

All Pine Street Inn employees must comply with Pine Street Inn’s occupational health policy.

Please email your cover letter and resume in confidence to:

Tara DiDomenico

Senior Consultant

Development Guild DDI

Related Posts

Interested in this position or other new career opportunities?