Director of Gift Planning

Westminster School; Simsbury (CT); On-site; USD 100,000 - 120,000; Full time

Benefits offered by this job

Health care coverage

Retirement plan

Paid time off

Job summary

Westminster School seeks a thoughtful, experienced Director of Gift Planning to lead and grow the school’s robust planned giving program. Reporting to the Director of Advancement, the Director of Gift Planning will be responsible for identifying, cultivating, soliciting, documenting and stewarding planned gifts that support Westminster’s long-term financial sustainability.

This frontline fundraising role will collaborate with annual giving, major gifts, stewardship and communications, overseeing

Qualifications

• Bachelor’s degree in relevant field is required.
• Minimum of 5 to 7 years of advancement, planned giving, major gifts, estate planning, financial services, or related experience preferred.
• Strong writing, presentation and interpersonal skills.
• Ability to explain complex giving concepts in clear, donor-centered language.
• High degree of discretion, judgment, and confidentiality.

Responsibilities

• Lead and manage Westminster’s planned giving program, including annual goals, donor strategy, marketing, stewardship and reporting.
• Develop a clear annual plan to increase planned gift commitments and grow Thring Society membership.
• Build and manage a portfolio of approximately 150 planned giving prospects and donors.
• Partner with senior leadership to integrate planned giving into broader fundraising strategy.
• Support blended gift conversations that combine annual, capital, endowment and planned gift opportunities.
• Prepare proposals, gift illustrations, letters of intent and other materials related to planned gifts.
• Maintain accurate documentation of planned gift intentions, estimated values, and donor preferences.
• Lead strategy for Thring Society stewardship and Seventh Form programming for senior alumni.

Skills

Relationship builder

Clear communicator

Strategic fundraiser

Discretion and confidentiality

Travel willingness

Education

Bachelor’s degree in relevant field

Tools

Raiser’s Edge NXT

Job description

Westminster School, one of the leading independent boarding schools in the country, is a diverse, close-knit community of approximately 190 employees and 430 male and female students (seventy-five percent boarding, twenty-five percent day students) set on a 200-acre campus in Simsbury, Connecticut. Since its founding in 1888, Westminster School has been committed to the core values of community, character, balance, and involvement. Our motto describes our community –“virtute et numine”– by Grit & Grace.

From a philanthropic perspective, Westminster is operating from a position of strength. The school completed a $102 million comprehensive campaign in 2021 and continues to build on that momentum. Today, fundraising centers on The Westminster Fund, which raises more than $3.2 million annually, as well as capital, endowed and donor-directed support for Westminster’s people, programs and strategic priorities. Together, these efforts generate more than $10 million in philanthropic support each year.

Gift planning will play an important role in Westminster’s next chapter. As the school prepares for future campaign planning, long-term financial sustainability and continued growth in endowed support, the Director of Gift Planning will help connect donor intent with Westminster’s enduring needs and future opportunities.

Position Summary

Westminster School seeks a thoughtful, experienced and relationship-centered Director of Gift Planning to lead and grow the school’s robust planned giving program. Reporting to the Director of Advancement, the Director of Gift Planning will be responsible for identifying, cultivating, soliciting, documenting and stewarding planned gifts that support Westminster’s long-term financial sustainability.

This role will manage Westminster’s planned giving strategy, including the Thring Society, legacy gift marketing, donor stewardship, partnership with the Seventh Form, blended gift conversations and collaboration with annual and major gift colleagues. The Thring Society recognizes the 336 members of the Westminster community who have shared their intention to include Westminster in their estate plans. The Seventh Form is Westminster’s engagement program for alumni who have celebrated their 50th reunion and beyond, and it serves as an important relationship and stewardship platform for the school’s most senior alumni.

The Director will work closely with alumni, parents, grandparents and friends who are interested in supporting Westminster through bequests, beneficiary designations, charitable gift annuities, charitable remainder trusts, retirement assets, gifts of real estate or other tangible personal property, appreciated securities, non-cash assets and other complex or deferred gifts.

The successful candidate will bring strong fundraising judgment, technical knowledge of gift planning vehicles, comfort with donor conversations and the ability to work appropriately with donors’ financial, legal and other professional advisors. This person must also be able to translate complex giving options into clear, donor-centered language.

This is a frontline fundraising role and an important strategic partner in Westminster’s campaign readiness, stewardship and long-term philanthropic growth. As a senior member of a 15-person Advancement Office, the Director of Gift Planning will collaborate closely across annual giving, major gifts, stewardship, advancement services, alumni engagement and communications to strengthen Westminster’s culture of philanthropy and secure resources for the school’s future.

Key Areas of Responsibility

Planned Giving Strategy

• Lead and manage Westminster’s planned giving program, including annual goals, donor strategy, marketing, stewardship and reporting.
• Develop a clear annual plan to increase planned gift commitments, deepen donor engagement and grow membership in the Thring Society.
• Build and manage a portfolio of approximately 150 planned giving prospects and donors, with emphasis on alumni, parents, grandparents and friends with demonstrated loyalty, capacity or long-term interest in Westminster.
• Partner with the Director of Advancement, Director of Advancement Operations, major gift officers and senior leadership to integrate planned giving into broader fundraising strategy.
• Support blended gift conversations that combine annual, capital, endowment and planned gift opportunities.
• Help shape gift planning strategy as part of Westminster’s long‑term campaign readiness work.

Donor Cultivation and Solicitation

• Identify, qualify, cultivate, solicit and steward planned giving prospects.
• Conduct regular donor visits, phone calls and written follow‑up with assigned prospects and Thring Society members.
• Prepare individualized strategies for planned giving prospects, including ask timing, gift vehicles, stewardship needs and next steps.
• Work with donors and their advisors as appropriate to support gift planning conversations while ensuring donors seek independent legal, tax and financial advice.
• Prepare proposals, gift illustrations, letters of intent and other materials related to planned gifts.
• Maintain accurate and ongoing documentation of planned gift intentions, estimated gift values and donor preferences, direction and restrictions.

Thring Society and Seventh Form Stewardship

• Lead strategy for the Thring Society, Westminster’s planned giving recognition society.
• Steward current Thring Society members through personal outreach, events, impact communications, birthday or milestone recognition and other meaningful touchpoints.
• Partner with Alumni Engagement to use Seventh Form programming as a key stewardship and cultivation channel for those alumni who have celebrated their 50th reunion, especially those with planned giving potential, existing Thring Society members and long‑term loyal donors.
• Collaborate on Seventh Form strategy, programming and follow‑up to strengthen relationships with Westminster’s most senior alumni and connect legacy engagement more intentionally to planned giving conversations and Thring Society stewardship.
• Ensure Thring Society listings, recognition materials and donor records are accurate and current.
• Partner with Advancement Communications and Stewardship to create donor stories, planned giving materials and impact content for the web, Thring newsletters and regular Bulletin ads that reflect Westminster’s mission and values.
• Partner with Alumni Engagement to develop thoughtful engagement opportunities for senior alumni and loyal donors through Seventh Form programming and other legacy‑focused stewardship.

Collaboration and Internal Partnership

• Serve as a planned giving resource and partner for Advancement colleagues, helping gift officers recognize opportunities, frame conversations, identify and structure planned, blended and complex gifts.
• Partner with Advancement Services to ensure accurate tracking of planned gift intentions, proposals, opportunities, contact reports and donor documentation in Raiser’s Edge NXT.
• Work with the Business Office and school leadership on gift acceptance, gift documentation, estate administration and reporting.
• Collaborate with Marketing and Communications on planned giving materials, website content, donor stories, social media and segmented outreach.
• Support volunteer engagement where appropriate, including class agents, reunion volunteers, Thring Society ambassadors and trustee partners.

Reporting, Data and Compliance

• Maintain accurate planned giving records in Raiser’s Edge NXT, including gift intentions, expected value, gift vehicle, restrictions, stewardship preferences and next steps.
• Produce regular reports on planned giving activity, pipeline, new commitments, realized bequests, Thring Society membership and estate administration.
• Track progress against annual goals, including visits, solicitations, commitments, new Thring Society members and stewardship activity.
• Ensure planned giving work follows Westminster policies, CASE standards, donor intent, privacy expectations and ethical fundraising practices.
• Stay current on planned giving trends, tax law changes, gift vehicles, donor behavior and best practices in independent school and higher education advancement.

Key Attributes

The successful candidate will be:

• A relationship builder who understands that planned giving is built through trust, time and careful listening.
• A clear communicator who can make complex gift planning options understandable and compelling.
• A strategic partner who can work across annual giving, major gifts, stewardship, advancement services and communications.
• A disciplined fundraiser who documents activity, tracks next steps and moves prospects forward.
• A careful steward of donor intent, donor confidentiality and Westminster’s long‑term interests.
• A colleague who brings warmth, professionalism and a strong sense of shared ownership to the Advancement Office.

Job Qualifications

• Bachelor’s degree in relevant field required.
• Minimum of 5 to 7 years of advancement, planned giving, major gifts, estate planning, financial services, or related experience preferred.
• Experience with Raiser’s Edge NXT or similar donor database preferred.
• Demonstrated success qualifying, cultivating, and soliciting donors for significant planned, blended, or complex gifts.
• Strong understanding of planned giving vehicles, including bequests, beneficiary designations, charitable gift annuities, charitable remainder trusts, retirement assets, real estate, and appreciated securities.
• Experience working with alumni, parents, trustees, volunteers, or other school‑based constituencies preferred.
• Strong writing, presentation, and interpersonal skills.
• Ability to explain complex giving concepts in clear, accessible, and donor‑centered language.
• High degree of discretion, judgment, and confidentiality.
• Ability to travel and work occasional evenings and weekends.

Compensation and Benefits

The employment package consists of excellent benefits, including outstanding health care coverage, retirement plan, and paid time off. The salary range for this role is $100,000-120,000 per year, commensurate with experience (higher compensation may be considered for exceptionally qualified candidates).

Westminster School is an Affiliated Action Equal Opportunity Employer and encourages applications from candidates of color. Westminster School reaffirms its long‑standing nondiscriminatory policy and employs individuals of any race, religion, sexual orientation, gender identity, or national origin to all the rights, privileges, programs, and activities generally accorded or made available at Westminster. Westminster does not discriminate in its hiring, educational policies, admissions policies, scholarship programs, or athletic and other school‑administered programs.

Notice of Nondiscriminatory Policy as to Students

In keeping with our support for a diverse community, Westminster abides by all applicable federal and state laws and does not discriminate on the basis of any protected characteristic, including race, color, religious creed, sex, sexual orientation, gender identity or expression, national and ethnic origin, ancestry and/or disability in administration of its educational policies, admissions policies, scholarship and loan programs, and athletic and other school‑administered programs. Westminster admits students of any race, color, national and ethnic origin to all the rights, privileges, programs, and activities generally accorded to students at the School.

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