Associate Director, Annual Fund

The Trustees of Reservations•Boston, MA

13d•$96,250 - $123,750•Hybrid

About The Position

As Associate Director of the Annual Fund, you’ll support the planning, execution, and growth of The Trustees’ comprehensive annual giving program. The Trustees’ Founders Circle is a highly segmented, multichannel leadership annual giving initiative that includes personalized solicitations and meaningful donor engagement opportunities. You’ll play a key role in managing core components of this $5+ million program by implementing annual giving strategies, coordinating donor messaging and communications, collaborating with the Events team to deliver impactful donor experiences, and ensuring the effective execution of appeals, renewals, and stewardship efforts. As the Associate Director, you’ll develop and implement a comprehensive annual giving strategy that aligns with organizational goals. Reporting to the Director of Development Operations, this highly collaborative position works across the Development team and with colleagues statewide to implement strategies that engage, retain, and grow the annual giving program. You will also lead stewardship efforts to strengthen donor relationships and inspire increased giving. The AD, Annual Fund, will design and implement a segmented, highly personalized, multi-channel annual giving program (direct mail, email, digital, events). Ensure personalized solicitations and stewardship for key donor segments and create meaningful donor experiences to deepen engagement and loyalty. In addition to these responsibilities, you’ll oversee the Annual Fund Coordinator, who is responsible for the daily execution of renewal solicitations and donor stewardship, and manage approximately 40% of the Development Associate’s responsibilities related to annual giving.

Requirements

7-10 years of professional fundraising experience, with a focus on annual giving, individual giving, or membership programs.
Demonstrated success managing mid-level donor portfolios, including cultivation, solicitation, and stewardship.
Experience coordinating annual fund campaigns, including multichannel solicitations, segmentation, and donor engagement strategies.
Strong writing and communication skills, with the ability to craft compelling donor messages and engagement materials.
Excellent project management and organizational skills, with the ability to manage multiple priorities, timelines, and deliverables.
Comfort working with CRM systems (Salesforce or similar), including querying, tracking activity, and ensuring data accuracy.
Strong analytical abilities with experience interpreting donor trends, campaign results, and fundraising performance metrics.
Ability to collaborate effectively across teams, including Major Gifts, Development Operations, Marketing/Communications, and regional staff.
High level of professionalism, discretion, and donor-centered service.
Ability to attend donor events, including occasional evenings or weekends as needed.
Commitment to the mission of The Trustees.
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.
A satisfactory criminal background (CORI) check.

Responsibilities

Support the management and execution of The Trustees’ comprehensive annual giving program, Founders Circle, helping to grow membership and achieve annual revenue goals.
Partner with and guide the Development Associate and Annual Fund Coordinator to deliver a high-quality, concierge experience for Founders Circle members, ensuring thoughtful stewardship and strong year-over-year retention.
Expand the Founders Circle base and safeguard the program's long-term health. Continue refining, streamlining, and boosting prospecting efforts.
Work closely with Membership to identify Founders Circle prospects within the general membership pool.
Record and manage all activities in the database for reporting purposes.
Deliver effective, cohesive, and compelling Founders Circle materials, appeals, and touchpoints by collaborating with the Development Communications Manager and Annual Fund Coordinator to create communications that foster belonging and community.
Assist Major Gift Officers with Founders Circle members in their portfolios by ensuring annual renewals, encouraging upgraded support, and coordinating major gift requests.
Collaborate with the Director of Governance to encourage engagement and participation among members of the leadership giving society.
Work with the Director of Development Operations and Finance Data Services team to resolve donor service issues, support data integrity, and ensure Founders Circle members receive timely and high-quality service.
Partner with the Annual Fund Coordinator and events team to help shape Founders Circle engagement opportunities and assist with planning a calendar of donor experiences throughout the year.
Participate in development events such as Annual Meetings, Founders Circle gatherings, signature events, and relevant Governance activities.
Maintain accurate tracking of Founders Circle activities, donor interactions, and results in the CRM database to support timely reporting and analysis.
Assist with preparing annual fund and prospect reports on a weekly, monthly, and annual basis.
Support budget monitoring and administrative processes for assigned annual fund cost centers.
Provide guidance and workflow coordination for select Development staff as assigned, helping ensure smooth collaboration, deliverables, and alignment with annual fund priorities.

Benefits

Sick time: 15 days per year
Vacation time: 20 days per year
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