Leadership Giving Officer

Pine Street Inn seeks a strategic, collaborative, and entrepreneurial Leadership Giving Officer to build and manage a newly formed $2.5K+ donor program that bridges well-established Annual Giving and Major Gifts functions. About Pine Street Inn Since opening its doors in 1969, Pine Street Inn has grown into New England’s largest and most comprehensive nonprofit homeless services provider. Over five decades, its work has evolved from meeting basic needs (food, clothing, shelter, and health care) to offering programs that enable guests to take meaningful steps in their journey out of homelessness and regain some of what they have lost (relationships, life skills, employment, and housing). Today, Pine Street delivers short-term remedies and lasting solutions to more than 2,000 individuals each day through a continuum of services rooted in dignity, consistency, and care. For more information, please visit About Philanthropy at Pine Street Inn Pine Street Inn is on strong financial footing and sustains its $100M annual operating budget through a healthy blend of private philanthropy and public funding. In FY2025, Pine Street raised more than $35M, including nearly $24M in unrestricted operating support. The organization has a robust donor community of 25,000+ and a deep, active volunteer base. Led by Chief Advancement Officer Becky Crawford, Pine Street’s Advancement division includes more than 30 staff across Annual Giving, Major and Planned Giving, Advancement Operations and Development Systems, Event and Volunteer Engagement, Institutional Giving, and Communications. Pine Street Inn’s Annual Fund is a sophisticated direct-response engine. It generates approximately $7M per year and is supported by robust mail, digital, acquisition, newsletter, and seasonal campaign strategies. That infrastructure is complemented by a mature Major Gifts program and a shared commitment to strengthening the donor experience across the full philanthropic pipeline. To support its next stage of growth, Pine Street is launching a Leadership Giving program dedicated to donors giving $2,500 and above annually. The program is designed to formalize engagement with this donor cohort, strengthen stewardship consistency, create clearer pathways between Annual Giving and Major Gifts, and ensure that donors at these levels have an impactful and mission-centered relationship with Pine Street. This will not be a traditional benefits-based giving society. Instead, the Leadership Giving program will translate Pine Street’s strong direct-response foundation and major-gift relationship orientation into a scalable engagement model that reflects the urgency, complexity, and humanity of the organization’s work. About the Position Reporting to the Director of Annual Giving and Donor Relations and working closely with the Senior Director of Major and Planned Giving, the Leadership Giving Officer (LGO) will serve as the operational and strategic lead for Pine Street’s newly developing Leadership Giving program. The LGO will help establish the infrastructure and engagement strategy that define how donors giving $2,500+ are stewarded, cultivated, and thoughtfully connected to Pine Street’s broader fundraising program. With ~850 donors in the current Leadership Giving threshold, this role offers a unique opportunity to bring structure, creativity, and relationship-based attention to a vital segment of Pine Street’s donor community. The LGO will function as a program builder, relationship manager, and internal connector. Rather than carrying a traditional major-gift portfolio, this person will manage donor engagement in a group-based model. They will serve as the primary point of contact for unassigned Leadership Giving donors and will coordinate with gift officers to ensure that assigned donors receive a consistent experience across Annual Giving, Leadership Giving, and Major Gifts. In their first year, the LGO will focus heavily on thoughtful discovery, planning, and phased implementation, including: learning Pine Street’s donor base, understanding how its well-established Annual Giving and Major Gifts programs currently operate, mapping existing communications and engagement opportunities, and organizing the details needed for eventual program rollout. The ideal candidate will bring creativity, patience, strong systems instincts, and the ability to translate donor data and relationship insights into scalable engagement strategies that support retention, upgrades, and long-term philanthropic growth. They will also be entrepreneurial, detail-oriented, donor-centered, and mission-driven. Key Responsibilities Program & Donor Engagement Serve as the operational lead for the Leadership Giving program and build the systems, workflows, documentation, and calendar needed to support long-term success. In partnership with the Chief Advancement Officer and colleagues in Annual Giving and Major Gifts, design and implement tiered engagement strategies for donors giving $2.5K and above annually, including donors at the $5K and $10K levels. Work with the team to develop creative, mission-aligned touchpoints such as small gatherings, programmatic conversations, on-site experiences, impact updates, volunteer opportunities, and other thoughtful forms of engagement. Coordinate acknowledgments, welcome outreach, stewardship touches, cultivation, and solicitation strategies for Leadership Giving donors, with an emphasis on operating support and sustainable donor growth. Identify donor movement, upgrade opportunities, and emerging pipeline trends in collaboration with Annual Giving, Advancement Operations, and Development Systems colleagues. Help translate Pine Street’s impact into compelling cases for support and donor communications at different giving levels. Ensure consistent, impact-focused communication across all leadership-level donor interactions. Build strong, trusted relationships across all facets of the Advancement division. Partner closely with Annual Giving and Development Systems to integrate Leadership Giving activity with direct response, segmentation, donor communications, renewal strategies, and database tracking. Work with Major Gifts colleagues to support donor transitions, surface upgrade opportunities, and maintain shared visibility across the pipeline. Collaborate with Communications to adapt existing stories, program updates, and impact content for Leadership Giving audiences. Lead or support regular coordination conversations that align donor engagement strategies, clarify ownership, manage cadence, reduce risk of donor fatigue, and keep efforts aligned across teams. Serve as a practical resource to colleagues on leadership donor engagement, segmentation, and moves management. Prioritize developing familiarity with Pine Street’s donor base, internal systems, team workflows, and current donor communication patterns before scaling program strategy. Establish and track key program benchmarks, including retention, upgrades, reactivation, engagement activity, and movement into major-gift portfolios. Use database insights, donor behavior, and relationship context to inform segmentation, cultivation, and stewardship strategies. Monitor and report on program performance to internal stakeholders. Codify lead-flow processes to determine when donors should remain in group-based engagement, receive additional qualification, or move toward Major Gifts management. Contribute to the long-term evolution of the Leadership Giving program as Pine Street continues to refine its philanthropic infrastructure. Key Qualifications 5-7 years of fundraising, annual giving, membership, donor relations, or related nonprofit experience. Demonstrated experience with donor engagement, pipeline development, upgrade strategy, and/or structured constituent engagement. Ability to manage relationships through a group-based, portfolio-adjacent, or multi-touch engagement model. Excellent interpersonal, writing, and communication skills. Strong organizational, systems-building, and project management skills, with exceptional attention to detail. Experience working with CRM systems (preferably Raiser’s Edge NXT), donor data, engagement tracking, reporting, and data-informed donor strategy. Ability to design or improve tiered donor engagement, stewardship, membership, or leadership annual giving programs. Creativity in developing meaningful donor touchpoints with limited resources. Highly collaborative style and proven ability to work across multiple teams. Sound judgment, patience, flexibility, and entrepreneurial interest in a developing role. Commitment to Pine Street Inn’s mission and comfort engaging with donors and guests. A bachelor’s degree is required. Compensation and Work Arrangement The salary for this position is $90,000-$105,000 per year, commensurate with experience. This full-time position is eligible for a hybrid work schedule in accordance with Pine Street Inn’s Remote Working Policy and requires regular on-site work, generally two days per week, with flexibility for additional on-site time and occasional evening, weekend, and holiday responsibilities as needed for donor engagement and events. 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. #J-18808-Ljbffr