Chief Development Officer

What You'll Do

• Your Impact: The Trustees is entering a transformational chapter in its history through the implementation of For Everyone, Forever, our bold strategic plan to save, steward, and share Massachusetts' special places for generations to come. As Chief Development Officer (CDO), you will play a critical leadership role in shaping the future of philanthropy at The Trustees—building the relationships, strategies, and culture necessary to sustain and grow support for our mission statewide.
• Specifically, you'll be responsible for:
• Leading a successful $300M+ comprehensive fundraising effort in support of our Strategic Plan, working closely with consulting partners, the CEO, CFO, Board leadership, and senior staff.
• Serving as a trusted advisor and strategic partner to the CEO, including proactively supporting leadership priorities, preparing for donor and Board engagement opportunities, and helping maximize executive effectiveness in fundraising and external relationship management across the organization.
• Developing and leading an integrated fundraising strategy that strengthens annual giving, major gifts, membership, institutional support, planned giving, and donor engagement to maximize long-term philanthropic growth and supporter lifetime value.
• Personally managing and soliciting a portfolio of the organization's highest-capacity donors, securing transformational and unrestricted gifts in partnership with the CEO and Board leadership.
• Driving the identification and cultivation of new major donor prospects and philanthropic audiences, broadening The Trustees' network of support and deepening donor engagement statewide.
• Prioritizing events strategy to align with major gift cultivation and donor engagement priorities, maximizing opportunities to deepen relationships and strengthen philanthropic outcomes.
• Ensuring high-quality, individualized, and meaningful stewardship of donors, coordinating with colleagues throughout The Trustees and/or personally stewarding donors as needed.
• Ensuring events strategy is aligned with major gift cultivation and donor engagement priorities, maximizing opportunities to deepen relationships and strengthen philanthropic outcomes.
• Developing and maintaining a strong understanding of The Trustees' programs, strategic priorities, and external landscape to effectively position the organization with donors and partners.
• Collaborating with Marketing and Communications colleagues to ensure consistent, compelling, and coordinated messaging across all fundraising and engagement channels.
• Working closely with the Finance Department to ensure the highest levels of customer service, compliance, gift processing accuracy, and stewardship reporting.
• Ensuring accurate allocation in line with donor intent and maintaining oversight of multi-year gifts and endowment reporting.
• Regularly reporting on fundraising performance, benchmarks, forecasts, and strategic opportunities to executive leadership and the Board.

Team Development and Management

• Oversee the hiring, training, mentoring, professional development, and evaluation of a talented Development team of 20 professionals.
• Audit and evolve the Development team structure, capabilities, and workflows to support organizational priorities, fundraising growth, and long-term sustainability.
• Lead organizational and team culture change efforts that foster collaboration, accountability, innovation, and a shared commitment to philanthropy across the organization.
• Set appropriate annual production goals and monitor progress regularly to maximize performance related to prospect strategy, cultivation, solicitation, stewardship, volunteer engagement, and events.
• Oversee growth, maintenance, and enhancement of the development team's technological proficiency and tools, including Salesforce CRM.
• In partnership with the Director of Development Operations, establish a data-driven fundraising operation, ensuring robust pipeline management, accurate forecasting, and strategic use of CRM systems to drive performance and decision-making.
• Set clear expectations around collaboration, communication, strategic priorities, and shared outcomes while motivating and inspiring the team during a period of organizational growth and change.

Exceptional Collaboration and Communication

• Regularly prepare detailed and transparent reports and analyses on Development Department activities for the CEO, Board leadership, and broader dissemination as appropriate.
• In collaboration with the CFO, establish and monitor fundraising benchmarks and long-term financial goals.
• Analyze development activities and benchmark against peer institutions to ensure The Trustees remains innovative, competitive, and aligned with fundraising best practices and emerging philanthropy trends.
• Serve as an ambassador for The Trustees, representing the organization externally with donors, partners, and stakeholders across Massachusetts and beyond.
• Travel as needed to support The Trustees' priorities, including donor cultivation and solicitation, strategic communications, and special events, which may take place on nights or weekends.

Requirements

• Skills and Experience:
• 15+ years of progressive leadership experience in fundraising and development, including significant experience leading complex, multi-faceted fundraising organizations and strategies.
• Proven track record of securing transformational and unrestricted gifts from high-net-worth individuals, family foundations, corporations, and institutional funders.
• Demonstrated success leading large-scale, multi-year fundraising initiatives or comprehensive campaigns, while also building sustainable fundraising strategies that extend beyond campaign goals.
• Deep expertise across a broad range of philanthropic disciplines, including Major Gifts, Annual Giving, Campaigns, Corporate and Foundation Relations, Planned Giving, Membership, Donor Stewardship, and Board Engagement.
• Experience developing and executing donor-centered fundraising strategies rooted in storytelling, relationship-building, and clearly communicating mission impact to diverse audiences.
• Strong ability to identify, cultivate, and engage new donor audiences, expanding philanthropic networks and pipelines.
• Experience partnering effectively with executive leaders, boards, and cross-functional teams to shape strategic fundraising priorities and translate organizational initiatives into compelling philanthropic opportunities.
• Demonstrated ability to lead organizational and cultural change efforts, including fostering collaboration, accountability, and an organization-wide culture of philanthropy.
• Exceptional strategic thinking skills with the ability to assess trends in philanthropy, donor behavior, financial markets, and the external landscape to inform fundraising strategy and organizational decision-making.
• Hands-on, adaptable leadership style with a willingness to operate strategically while also engaging directly in the day-to-day work needed to advance fundraising priorities and organizational goals.
• Exceptional written communication skills, with the ability to craft compelling donor communications, fundraising proposals, strategic narratives, and impact-driven messaging tailored to diverse audiences.
• Strong analytical capabilities with experience using data, metrics, and forecasting to inform fundraising strategy, assess performance, identify opportunities, and support strategic decision-making.
• Systems thinker with the ability to understand the interconnectedness of teams, functions, donor engagement strategies, and organizational goals.