Chief Development Officer

The Trustees of Reservations•Boston, MA

1d•Hybrid

About The Position

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. While The Trustees is currently engaged in the largest fundraising effort in the organization’s history, this role is about far more than leading a campaign. It is an opportunity to help evolve how The Trustees connects mission to philanthropy by building a fundraising strategy that deepens engagement, expands philanthropic support, and inspires new audiences and institutions to invest in our work. As a member of the executive team, you’ll help lead the organization through a period of strategic and cultural evolution—strengthening collaboration across teams, fostering an organization-wide culture of philanthropy, and helping programmatic and functional leaders translate their expertise into compelling philanthropic opportunities. You’ll partner across the organization to shape fundraising priorities and create compelling investment opportunities that resonate with donors and reflect the impact and relevance of The Trustees’ mission. This role requires a strategic and adaptable fundraising leader with a strong track record of securing transformational and unrestricted support, cultivating new donor relationships, and navigating complex organizational environments. You’ll bring a sophisticated understanding of donor motivations across philanthropic sectors, philanthropy trends, and external market dynamics, while helping position The Trustees for long-term fundraising success and mission impact. You will have significant team management experience and the ability to lead culture change and inspire success. As the Chief Development Officer (CDO), you’ll provide enterprise-wide, strategic leadership on Trustees development activities, including oversight of a comprehensive fundraising strategy that advances the organization’s strategic priorities and long-term sustainability. As a key member of the executive team, you will lead and help successfully execute The Trustees’ historic $300M+ comprehensive campaign in support of For Everyone, Forever while also strengthening the long-term fundraising infrastructure, donor relationships, and culture of philanthropy needed to sustain impact well beyond the campaign itself. In partnership with the President and CEO, CFO, Board Development Committee, campaign leadership, and senior leadership team, you will set annual, campaign, and long-term fundraising goals for The Trustees. You’ll construct development strategies and execute plans aligned with The Trustees’ overall Strategic Plan, with a focus on sustaining annual giving revenue levels, increasing unrestricted philanthropic support, expanding major donor engagement, and successfully advancing campaign priorities and milestones.

Requirements

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 priorities, and to build collaborative, integrated approaches that drive long-term success.
Strong situational awareness, sound judgment, and the ability to navigate complex organizational environments with diplomacy, adaptability, and emotional intelligence.
Proven experience leading, mentoring, and developing large high-performing teams, including managing experienced fundraising professionals through periods of growth and change.
Experience building and overseeing data-driven fundraising operations, including campaign forecasting, pipeline management, performance benchmarking, and strategic use of CRM systems such as Salesforce.
Excellent communication and relationship-building skills, with the ability to serve as a persuasive ambassador, listener, collaborator, and translator between programmatic experts and donor interests.
Strong project management and organizational skills, with the ability to balance strategic leadership and hands-on execution.
Current authorization to work in the United States – a candidate must have such authorization by his or her first day of employment.
A valid driver’s license, as well as a satisfactory driving record as outlined in The Trustees’ driving policy. [if needed]
A satisfactory criminal background (CORI) check.

Nice To Haves

Passion for conservation, climate resiliency, cultural preservation, public engagement, or mission-driven nonprofit work preferred.

Responsibilities

Lead 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.
Serve 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.
Develop and lead 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 manage and solicit a portfolio of the organization’s highest-capacity donors, securing transformational and unrestricted gifts in partnership with the CEO and Board leadership.
Drive the identification and cultivation of new major donor prospects and philanthropic audiences, broadening The Trustees’ network of support and deepening donor engagement statewide.
Partner with and mobilize the Board of Trustees to advance fundraising goals, equipping members to effectively engage, cultivate, and solicit donors.
Serve as a strategic thought partner to programmatic and functional leaders, helping shape mission-driven initiatives into compelling funding opportunities and narratives that are relevant to donors.
Help evolve The Trustees’ fundraising approach toward storytelling and impact-centered engagement, ensuring donors clearly understand the tangible outcomes of their philanthropic investment.
Ensure high-quality, individualized, and meaningful stewardship of donors, coordinating with colleagues throughout The Trustees and/or personally stewarding donors as needed.
Ensure events strategy is aligned with major gift cultivation and donor engagement priorities, maximizing opportunities to deepen relationships and strengthen philanthropic outcomes.
Develop and maintain a strong understanding of The Trustees’ programs, strategic priorities, and external landscape to effectively position the organization with donors and partners.
Collaborate with Marketing and Communications colleagues to ensure consistent, compelling, and coordinated messaging across all fundraising and engagement channels.
Work closely with the Finance Department to ensure the highest levels of customer service, compliance, gift processing accuracy, and stewardship reporting.
Ensure accurate allocation in line with donor intent and maintain oversight of multi-year gifts and endowment reporting.
Regularly report on fundraising performance, benchmarks, forecasts, and strategic opportunities to executive leadership and the Board.
Oversee the hiring, training, mentoring, professional development, and evaluation of a talented Development team of 20 professionals.
Assess 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.
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.

Benefits

Unlimited PTO
12 observed holidays, 3 floating
Health insurance: You are eligible to participate in the Trustees health insurance benefit via Blue Cross Blue Shield (BCBS). BCBS also offers additional benefits, such as fitness reimbursement and rewards for healthy habits.
Short-Term and Long-Term Disability Insurance
Massachusetts Paid Family Medical Leave
Life Insurance
401k with 5% match after 1 year of employment
Employee Assistance Program: Free access to a confidential service that helps employees and their communities with personal and work-related issues, such as mental health support, counseling, and financial advice.
Reciprocity: Employees have access to free and discounted admission and membership to more than 50 nearby museums and cultural institutions.
Discounts: Enjoy free entry to all Trustees properties, discount event tickets, and discounted merchandise at our stores and on stays at our inns.
Day of Wonder: Spend one workday per year to exploring a Trustees property
Day of Service: Spend one workday per year to helping with a project at a Trustees property