Senior Major Gifts Officer

December 2022 | Hybrid / Boston, MA
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Pine Street Inn seeks a Senior Major Gifts Officer to join its high performing         Major and Planned Giving Program

About Pine Street Inn

Pine_Street_Inn_Tenant_CroppedPine 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. 

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 five 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 participate in job training programs each year.
  • Street Outreach – Pine Street’s day and night street outreach teams travel throughout Greater Boston to offer food, blankets, health care and access to shelter and housing to unsheltered men and women. 

Today, Pine Street Inn serves over 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

woman handing a man a set of keys at pine street innPine Street’s $84M annual operating budget is primarily funded through government grants and private philanthropy. Last year, Pine Street raised more than $24M, of which $17M was in unrestricted support. Pine Street has a robust donor community of more than 30,000 and engages more than 5,000 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 has 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

The Senior Major Gifts Officer (SMGO) will join Pine Street Inn as it builds upon the tremendous success of its $50 million campaign, which further solidified Pine Street’s nationally recognized reputation as a trailblazer in conquering homelessness. The SMGO will join a high-caliber individual giving program that reflects Pine Street’s culture, mission, goals, and bold strategic plan.

Reporting to the Senior Director of Major and Planned Giving, the SMGO will work collaboratively and transparently with the executive team, board members, senior leadership, staff, and volunteers to build on the momentum of the recently completed campaign and the surge in pandemic-era giving, developing relationships with new prospects and taking relationships with existing donors to the next level. They will assist in driving an ongoing organization-wide conversation about vision, strategy, idea generation and goals for development.

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

Key Responsibilities

With deep knowledge of best practice major gift strategies, including personal experience developing pipelines, the SMGO will be a strategic, creative, ambitious, and dynamic externally facing fundraiser with the ability to build upon Pine Street’s fundraising momentum and achievements. A mission driven and team oriented professional, the SMGO will:

  • Develop relationships with new and existing donors while managing a portfolio of approximately 150-175 people
  • Be entrepreneurial minded and contribute to the growth of the major gifts program, continually striving to improve and extend relationships with donors and prospects in ways that have a quantifiable impact on philanthropic revenue
  • Embrace technological and analytical solutions with a keen sense of what is possible and a level of excellence in communication and collaboration skills
  • Be a team player with a demonstrated propensity for weaving development into organizational values and aspirations
  • Accurately and passionately communicate the mission and values of PSI to current donors and prospects
  • Effectively identify new prospects from a variety of sources, including the existing database, a dedicated corps of 5,000 individual and institutional volunteers annually, and community philanthropists
  • Build cultivation and stewardship programs to support major gift solicitations and develop a healthy pipeline of prospective donors
  • Solicit donors for annual gifts and special projects

Key Qualifications

The successful candidate will be a strategic and creative fundraiser who can support Pine Street’s vision for philanthropy while maximizing results. The SMGO will have an appreciation for diverse perspectives and will possess outstanding interpersonal competencies, the ability to effectively engage donors and volunteers, and a deep commitment to instilling best practices that reflect Pine Street’s values.

  • 4-7 years of progressively responsible experience in a successful individual giving program or a relevant field  
  • Proven track record in managing individual relationships and securing five to six-figure gifts   
  • Strong verbal and written communication skills, presentation skills, and analytical skills
  • Experience with managing and engaging Board level volunteers
  • Commitment to the mission of Pine Street Inn
  • Self-motivated and entrepreneurial approach to work
  • Strong commitment to working in a collaborative environment
  • A metrics-driven mindset that informs strategy
  • Thorough, organized, strategic, and creative approach to major gifts work
  • Flexibility, tenacity, sense of humor, a team player
  • Proficiency in Raiser’s Edge and Microsoft Office
  • Openness to travel within Massachusetts for donor visits or as the organization’s representative
  • A bachelor’s degree or equivalent experience
  • Some weekend, evening, and 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 

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