Director of Major Gifts & Legacy Giving

Description

About The Overlake School

At Overlake, students are known, challenged, and supported as individuals. Academic rigor is complemented by meaningful experiences in the arts, athletics, outdoor education, service, and community engagement. Our faculty and staff cultivate an environment where students develop the confidence to ask questions, think critically, embrace challenges, and discover who they are becoming.

Philanthropy has helped shape the Overlake experience across generations, expanding educational opportunities, supporting exceptional teaching, strengthening financial aid, and investing in the school's long-term future. As Overlake looks ahead, we are seeking an experienced and thoughtful fundraising professional who understands the power of enduring relationships and can inspire meaningful philanthropic investment in the school and its students.

The Details:

Reports to: Chief Development Officer

Wage: $120,000 - $130,000, Salaried Exempt commensurate with qualifications and experience.

Work Hours and Location: This is an on-site position and is eligible for flexible work hours, M-F, between the hours of 7am - 6pm. The role requires occasional evening and weekend commitments for donor engagement, school events, and other institutional activities, along with occasional local or regional travel.

The Process:

Please submit your résumé and a brief written response (300 words maximum) to one of the following questions in lieu of a traditional cover letter. Please omit donor names and identifying information.

Option 1: Moving a Major Gift to Commitment

Tell us about a significant gift you personally helped secure, ideally one that represented a meaningful increase in a donor's previous giving. How did you assess the donor's readiness, develop your approach, and move the relationship toward a solicitation? What was your specific role, what was the outcome, and what did you learn?

OR

Option 2: Building Relationships That Inspire Long-Term Philanthropy

Describe a donor relationship you developed where the donor's philanthropic interests were not initially aligned with your organization's priorities, or where the opportunity for a significant commitment was not immediately apparent. How did you build trust, discover what mattered to the donor, and translate that understanding into a meaningful philanthropic opportunity? What actions did you personally take, and what was the outcome?

Benefits:

• $5 employee premium for all medical plans
• 100% employee coverage for dental and vision plans
• 35% medical, dental and vision coverage for dependents
• 20 to 30 days of paid time off based on tenure for full-time 12-month staff
• Paid Holidays when school is fully closed
• 5-10% employer match based on years of service and employee contribution
• On-site health and wellness
• Professional development allowance
• Meal allowance for breakfast, lunch, and snacks through on-campus dining.
• Employee Assistance Program
• Long term and short term disability as well as life insurance
• Use of School Library

Position Overview

The Director of Major Gifts & Legacy Giving will serve as a senior frontline fundraiser, responsible for personally cultivating, soliciting, and stewarding major donor relationships, securing significant philanthropic commitments, and developing a sustainable pipeline of legacy giving opportunities.

Reporting to the Chief Development Officer, the Director will manage an active portfolio of approximately 50–75 qualified donors and prospective supporters, with responsibility for advancing relationships from discovery and cultivation through solicitation, commitment, and stewardship.

The role will engage current parents, alumni, parents of alumni, grandparents, trustees, and other members of the Overlake community, connecting their philanthropic interests with the school's educational mission and institutional priorities.

Approximately 80% of the position will focus on direct fundraising and donor engagement, including major gifts and legacy giving conversations. The remaining 20% will support major gifts strategy, legacy giving program development, and readiness for future capital and endowment initiatives.

The successful candidate will bring a demonstrated record of personally securing six-figure gifts, the experience and judgment to pursue larger commitments, and the ability to engage donors in thoughtful conversations about both immediate and long-term philanthropic support.

This is a senior, hands-on individual contributor position with no supervisory responsibilities. The Director will work closely with the Chief Development Officer, Head of School, trustees, and Development colleagues while maintaining direct accountability for donor relationships, solicitation activity, and fundraising outcomes.

We are looking for someone who brings genuine curiosity about people, strong fundraising instincts, exceptional follow-through, and a deep appreciation for the transformative role philanthropy can play in education.

Key Responsibilities

Major Gifts and Donor Relationships (80%)

Portfolio Management and Fundraising

• Personally manage a portfolio of approximately 50–75 qualified major donors and prospects, adjusting strategies based on donor interest, capacity, engagement, and readiness.
• Develop and execute individualized donor strategies that advance relationships from qualification and cultivation through solicitation, commitment, and stewardship.
• Personally solicit and secure significant philanthropic commitments, including six-figure gifts, and cultivate opportunities for larger and potentially transformational investments.
• Identify and qualify new major gift prospects, including current and former families, alumni, grandparents, and other members of the Overlake community.
• Build trusted, enduring donor relationships by listening carefully, understanding philanthropic motivations, and connecting interests with Overlake's mission and priorities.
• Identify opportunities to increase giving, secure multi-year commitments, and deepen long-term philanthropic engagement.
• Maintain consistent personal contact with donors through substantive meetings, campus visits, discovery conversations, tailored engagement opportunities, and thoughtful follow-up.
• Partner with the Chief Development Officer, Head of School, trustees, and other institutional leaders on significant donor relationships, including preparing leaders for cultivation and solicitation conversations.
• Maintain accurate and timely donor records, including contact reports, solicitation strategies, next steps, anticipated commitments, and fundraising forecasts.

Legacy Giving and Long-Term Philanthropic Relationships

• Identify, cultivate, and solicit donors interested in making lasting commitments to Overlake through bequests and other planned giving arrangements.
• Integrate legacy giving conversations naturally into existing major donor relationships, particularly with alumni, former families, grandparents, and longtime supporters.
• Develop individualized strategies for prospective legacy donors, recognizing that planned giving decisions often evolve through sustained relationships and conversations.
• Partner with the Chief Development Officer to grow and strengthen Overlake's legacy giving pipeline and deepen awareness of opportunities to support the school beyond one's lifetime.
• Facilitate conversations about bequests, beneficiary designations, retirement assets, and other planned giving opportunities, working with donors' professional advisers and qualified specialists when appropriate.
• Secure and appropriately document confirmed legacy intentions, coordinating with Development colleagues and school leadership to ensure accurate records and responsible stewardship.
• Collaborate on meaningful recognition and stewardship opportunities for donors who have included Overlake in their estate plans.
• Help strengthen Overlake's culture of lifelong philanthropy by building lasting relationships with alumni and families beyond their years of direct involvement with the school.

Major Gifts Strategy, Legacy Giving Development, and Campaign Readiness (20%)

• Partner with the Chief Development Officer to strengthen Overlake's major gifts program and build a sustainable pipeline of leadership and transformational donors.
• Help develop a coordinated legacy giving strategy, including prospect identification, donor engagement, communications, recognition, and stewardship.
• Contribute to fundraising strategies for institutional priorities, including the Overlake Fund, financial aid, endowment, academic and co-curricular programs, and potential future capital initiatives.
• Support campaign-readiness planning through prospect analysis, leadership gift identification, donor qualification, and preliminary cultivation strategies.
• Apply insights from prior fundraising initiatives to inform future major gift and campaign approaches.
• Collaborate on philanthropic cases for support that clearly connect institutional priorities with compelling educational outcomes.
• Coordinate major gift and legacy giving strategies with annual giving, alumni engagement, and stewardship efforts to create a coherent donor experience.
• Provide thoughtful recommendations regarding donor readiness, solicitation timing, philanthropic capacity, and opportunities for significant investment.

Collaboration and Accountability

The Director will work within a collaborative Development team, with colleagues providing specialized support so the role can remain focused on donor relationships, solicitations, and philanthropic commitments.

Performance will be evaluated through:

• Major gifts and philanthropic commitments personally secured.
• Progress toward agreed-upon annual fundraising goals.
• Meaningful donor engagement, qualification, and solicitation activity.
• Advancement of qualified prospects through documented stages of relationship development.
• Increased giving, multi-year commitments, and retention within the assigned portfolio.
• New legacy giving prospects identified, meaningful planned giving conversations, and confirmed documented intentions.
• Quality of donor stewardship and long-term relationship development.
• Accurate portfolio records, reliable fundraising forecasts, and consistent follow-through.
• Effective collaboration with school leadership and Development colleagues.

Individual fundraising goals, solicitation expectations, and legacy giving performance measures will be established in partnership with the Chief Development Officer, taking into account portfolio maturity, donor readiness, and institutional priorities.

The Director will provide regular updates on fundraising activity, anticipated commitments, emerging opportunities, and challenges, with clear recommendations for advancing significant gifts.

Within the first year, the Director will have:

• Established and actively managed a well-qualified portfolio of approximately 50–75 donors and prospective supporters.
• Built substantive relationships with priority donors and developed individualized strategies for advancing significant gift opportunities.
• Personally solicited and secured major gifts toward agreed-upon fundraising goals.
• Identified and engaged prospective legacy donors, advanced planned giving conversations, and documented new commitments where donors are ready.
• Strengthened the pipeline of leadership and transformational gift opportunities that can support Overlake's future priorities.
• Established clear, reliable portfolio reporting and forecasting practices that inform fundraising decisions and leadership engagement.

Over time, the Director will contribute to a stronger culture of lifelong philanthropy, where families, alumni, and friends see themselves as enduring partners in Overlake's mission.

Requirements

• Demonstrated success personally cultivating, soliciting, and securing six-figure philanthropic gifts.
• Significant professional experience managing major donor relationships and an active portfolio of individual prospects.
• Strong understanding of major gifts fundraising, including donor qualification, individualized solicitation planning, moves management, stewardship, and pipeline development.
• Demonstrated ability to develop donor relationships that result in increased giving and significant philanthropic commitments.
• Knowledge of planned giving concepts and the ability to engage donors in conversations about long-term philanthropic intentions.
• Excellent relationship-building skills and the ability to establish trust and credibility with donors, institutional leaders, trustees, and colleagues.
• Sound fundraising judgment, strong listening skills, and the ability to understand donor motivations and identify meaningful philanthropic opportunities.
• Exceptional written and verbal communication skills, including the confidence to articulate compelling funding opportunities and personally make significant asks.
• Strong organizational skills, attention to detail, and the ability to manage multiple donor relationships and fundraising priorities.
• Experience using fundraising CRM systems and donor data to manage relationships, document activity, and forecast commitments.
• A proactive, collaborative approach and demonstrated accountability for fundraising outcomes.
• Genuine commitment to Overlake's mission, student-centered education, and inclusive community.

Preferred Requirements

• Experience in independent-school advancement, higher education, or a similarly relationship-centered philanthropic organization.
• Demonstrated experience cultivating, soliciting, or securing seven-figure gifts.
• Experience identifying, soliciting, and stewarding legacy or planned giving commitments.
• Familiarity with bequests, beneficiary designations, charitable trusts, and other planned giving vehicles.
• Experience contributing to capital, endowment, or comprehensive fundraising campaigns.
• Experience partnering with heads of school, presidents, trustees, or other senior leaders on major donor relationships and significant solicitations.
• Experience engaging alumni, current and former families, and multigenerational donor relationships.
• Experience with Raiser's Edge or a comparable fundraising CRM.
• Familiarity with CASE and AFP fundraising standards, donor confidentiality, and ethical philanthropic practices.

Above all, we are looking for a fundraiser who knows how to build trust, listen deeply, recognize philanthropic opportunities, make meaningful asks, and secure significant gifts.

The impact of this work will be reflected in the experiences available to students today and the opportunities Overlake can create for generations to come.

Equal Employment Opportunity

At The Overlake School, we strive to ensure that every employee feels welcomed and valued for their unique perspectives and contributions. From our hiring practices, performance reviews, raise decisions, and opportunities for promotions, The Overlake School follows consistent and fair practices to ensure all employees and potential employees have an equal opportunity for employment and advancement based on merit, and are not discriminated against because of race, color, religion, national origin, age, sex, veteran status, pregnancy, childbirth, pregnancy-related conditions, disability, gender, gender identity, sexual orientation, or on any other legally protected basis in the administration of its educational policies, financial aid, employment, and other school-administered programs. Our Human Resources department works with employees to make reasonable accommodations for those that require assistance in being able to participate in the interview process or meet the requirements of their position.

Background Check Policy

The Overlake School conducts background checks for employees after the conditional offer of employment is accepted, in compliance with applicable federal, state, and local laws. Candidates will be asked to authorize these screenings and results will be reviewed by a designated HR representative. The Overlake School reserves the right to modify this policy at any time without notice.

Work Authorization Policy

This role is contingent upon the Employee’s ability to lawfully work in the United States in a manner compatible with the structure, schedule, and duration of the position. Any employment authorization that requires institutional agreements, academic-credit participation, or third-party oversight is subject to the School’s review and written approval.