Director – Annual & Leadership Giving

Description

Director, Annual & Leadership Giving

Department: Development

Reports To: Chief Development Officer

Classification: Full-Time, Exempt

Location: Dallas, Texas preferred. Hybrid or remote work options may be considered based on candidate experience, qualifications, and organizational needs.

Position Summary

The Director, Annual & Leadership Giving is a frontline fundraising professional responsible for identifying, qualifying, cultivating, soliciting, and stewarding donors with the potential to make annual gifts of $5,000 to $25,000 in support of the Commemorative Air Force (CAF) and the Henry B. Tippie National Aviation Education Center (NAEC).

Reporting to the Chief Development Officer, the Director will build and manage a portfolio of annual and leadership giving prospects, with a significant portion of the portfolio developed by identifying promising donors from the organization's direct response fundraising program and other constituent audiences.

The Director will engage donors personally and develop individualized strategies designed to deepen their connection to the mission and increase their philanthropic support. The goal is to move qualified prospects from transactional or lower-level giving into meaningful, relationship-based annual gifts of $5,000 to $25,000.

Leadership annual giving represents a critical source of sustainable philanthropic support for CAF and NAEC and serves as an important bridge between broad-based annual giving and major philanthropy. The Director will be responsible for strengthening this donor community while developing a consistent pipeline of future major and planned giving prospects.

The successful candidate will be an entrepreneurial and relationship-focused fundraiser who enjoys discovering donor potential, building relationships, and personally asking for financial support. This individual will combine strong interpersonal skills with a disciplined, data-informed approach to prospect qualification and portfolio management.

Essential Duties and Responsibilities

Prospect Identification & Qualification

• Build a portfolio of prospective annual and leadership donors primarily through the identification and qualification of donors emerging from the organization's direct response fundraising program and other constituent audiences.
• Regularly review donor activity to identify individuals demonstrating giving frequency, loyalty, increased giving, organizational engagement, philanthropic capacity, or other indicators of potential.
• Qualify prospects through personal outreach, discovery conversations, research, and engagement to determine philanthropic interests, capacity, and inclination.
• Engage promising donors regardless of their current giving level when available information suggests the potential for significantly increased philanthropic support.
• Develop qualification strategies designed to determine whether prospects have the interest and capacity to make annual gifts of $5,000 to $25,000.
• Partner with the Database Administrator and Chief Development Officer to establish and refine criteria for identifying prospective leadership annual giving donors.
• Maintain an active qualification pipeline to ensure a consistent flow of new prospects into the managed portfolio.
• Promptly return prospects who do not warrant individualized portfolio management to appropriate annual giving or stewardship strategies.

Leadership Giving & Portfolio Management

• Build and manage a portfolio of approximately 125–175 qualified donors and prospects with the potential to make annual gifts of $5,000 to $25,000.
• Develop individualized strategies for the cultivation, solicitation, and stewardship of assigned donors and prospects.
• Establish meaningful relationships through personal visits, telephone and video conversations, email, events, and other individualized engagement.
• Maintain a consistent schedule of donor qualification, cultivation, solicitation, and stewardship activity.
• Personally solicit donors for annual gifts within the $5,000–$25,000 leadership giving range.
• Develop appropriate ask amounts and solicitation strategies based on donor history, interests, engagement, and philanthropic capacity.
• Prepare personalized proposals, correspondence, presentations, and other donor materials as appropriate.
• Establish annual revenue and activity goals for the assigned portfolio.
• Maintain accurate projections and forecasts for assigned donors and prospects.
• Maintain accurate and timely records of donor contacts, strategies, proposals, solicitations, and next steps in Raiser’s Edge.
• Coordinate with the Chief Development Officer on significant donor relationships and solicitation strategies.
• Identify donors whose capacity, engagement, or philanthropic interests indicate readiness for major or planned giving strategies and facilitate an intentional transition when appropriate.

Annual & Leadership Giving Strategy

• Develop strategies to grow the number of donors making annual gifts of $5,000 to $25,000.
• Strengthen leadership annual giving as a core source of sustainable philanthropic revenue for CAF and NAEC.
• Develop strategies for increasing donor retention, renewal, consecutive-year giving, and upgrades within the leadership giving portfolio.
• Create intentional pathways for donors to progress from broad-based annual giving into leadership giving.
• Develop appropriate recognition, engagement, and stewardship strategies for leadership annual donors.
• Evaluate opportunities to strengthen or establish annual giving societies that recognize and encourage sustained giving at leadership levels.
• Develop strategies for increasing giving within the $5,000–$25,000 range and encouraging multi-year donor relationships.
• Use donor and portfolio performance data to refine qualification, cultivation, solicitation, and stewardship strategies.
• Ensure leadership giving serves as a strong pipeline for future major and planned gifts.

Donor Pipeline Development

• Use the organization's direct response donor base as a primary source for identifying prospective leadership annual giving donors.
• Regularly analyze giving history, recency, frequency, cumulative giving, organizational engagement, and available capacity information to identify prospective portfolio donors.
• Develop intentional strategies for moving qualified direct response donors from transactional giving into personalized cultivation and relationship-based fundraising.
• Identify opportunities among CAF members, volunteers, event attendees, and other organizational constituents who demonstrate philanthropic potential.
• Develop strategies for reengaging lapsed donors with leadership giving potential.
• Maintain a healthy balance between active qualification prospects and established portfolio donors.
• Identify leadership donors with the capacity and inclination to progress into major and planned giving relationships.
• Establish clear donor pathways from direct response and annual giving through leadership, major, and planned giving.
• Participate in regular portfolio and pipeline reviews with the Chief Development Officer.

Donor Stewardship & Retention

• Develop personalized stewardship strategies that strengthen relationships and demonstrate the impact of donor support.
• Ensure assigned donors receive timely, meaningful, and appropriate stewardship.
• Develop strategies to retain donors within the $5,000–$25,000 annual giving range and encourage increased and consecutive-year support.
• Identify opportunities for personalized outreach following significant gifts, organizational milestones, events, or other meaningful engagement.
• Partner with Development staff to develop appropriate donor recognition and stewardship activities.
• Work collaboratively with program staff to gather stories, outcomes, and impact information for donor communications.
• Connect donors with programs, aircraft, educational initiatives, events, and other areas of the mission aligned with their interests.
• Create opportunities for donors to experience the impact of their philanthropy firsthand.
• Participate in donor gatherings, organizational events, aviation events, and other cultivation and stewardship opportunities.

Recurring & Sustained Giving

• Identify recurring and long-term annual donors who demonstrate potential for leadership-level philanthropic support.
• Develop personalized strategies to transition qualified recurring donors into annual gifts of $5,000 or more when appropriate.
• Encourage sustained and multi-year philanthropic relationships among leadership annual donors.
• Partner with Development Operations and the Database Administrator to identify giving patterns and opportunities for increased engagement.
• Identify donors whose consistent giving demonstrates potential for major or planned giving conversations.

Event Sponsorships

• Identify event sponsorship opportunities among assigned donors, prospects, members, and appropriate business relationships.
• Solicit individual and business prospects for sponsorships that fall within or complement the Director's leadership giving portfolio.
• Incorporate sponsorship opportunities into broader cultivation strategies when aligned with a donor's interests and philanthropic goals.
• Partner with the Chief Development Officer and other Development staff on sponsorship strategies for key CAF and NAEC events.
• Coordinate with the Director of Institutional Giving & Strategic Partnerships on corporate sponsorship opportunities to ensure appropriate relationship management and avoid duplication of outreach.
• Steward event sponsors with the goal of developing ongoing philanthropic relationships beyond a single event or sponsorship.

Collaboration & Fundraising Support

• Work closely with the Chief Development Officer to establish leadership giving priorities, portfolio goals, revenue expectations, and donor strategies.
• Collaborate with the Director of Institutional Giving & Strategic Partnerships to coordinate individual, corporate, foundation, and sponsorship relationships when appropriate.
• Partner with the Manager, Development Operations and Gift Administration to ensure effective gift administration, acknowledgment, and stewardship processes.
• Work with the Database Administrator on prospect identification, portfolio management, donor segmentation, reporting, prospect screening, and fundraising analytics.
• Work with the Development Coordinator on donor communications, meetings, stewardship activities, events, and fundraising projects.
• Collaborate with Membership to identify CAF members with potential for deeper philanthropic engagement.
• Coordinate with Marketing, Education, Events, Units, and other organizational teams to develop meaningful donor engagement opportunities.
• Support the Chief Development Officer in engaging Board members, Development Committee members, senior leadership, and other volunteers in donor cultivation and solicitation.
• Prepare donor briefings and other materials for organizational leadership and volunteers participating in fundraising activities.

Reporting & Performance Management

• Establish annual portfolio revenue and activity goals in collaboration with the Chief Development Officer.
• Monitor progress toward leadership giving revenue and portfolio goals.
• Maintain accurate revenue forecasts for assigned donors and prospects.
• Track the number and value of qualified prospects entering the portfolio.
• Monitor donor retention, renewal, upgrades, solicitations, and movement into the $5,000–$25,000 leadership giving range.
• Track movement of qualified donors into major and planned giving pipelines.
• Use fundraising data to identify trends and recommend adjustments to strategy.
• Participate in regular Development team portfolio and pipeline reviews.
• Ensure donor interactions, proposals, solicitations, and strategies are documented accurately and promptly in Raiser’s Edge.

Performance Expectations

Performance will be evaluated through a combination of fundraising results, portfolio development, donor retention, pipeline growth, and meaningful fundraising activity, including:

• Total revenue generated from the assigned portfolio.
• Growth in the number of donors making annual gifts of $5,000 to $25,000.
• Number of prospects successfully qualified for leadership giving.
• Number of donors upgraded into the $5,000–$25,000 giving range.
• Leadership donor retention and renewal rates.
• Number and value of completed solicitations.
• Number of meaningful donor contacts, discovery conversations, and personal visits.
• Number of direct response donors successfully transitioned into personalized portfolio management.
• Number of lapsed donors successfully reengaged.
• Number of leadership donors identified and transitioned into major or planned giving strategies.
• Event sponsorship revenue generated from assigned relationships, as appropriate.
• Portfolio movement and progression through the donor cultivation cycle.
• Accuracy and timeliness of Raiser’s Edge documentation and revenue forecasting.

Specific annual revenue, qualification, solicitation, and activity goals will be established in collaboration with the Chief Development Officer.

Requirements

Qualifications

 This is a civilian position and does not require military service (including commissions and enlistment). 

Required

• Bachelor's degree or equivalent combination of education and relevant professional experience.
• Minimum of five years of progressively responsible fundraising, development, sales, relationship management, or comparable experience.
• Demonstrated success developing relationships with donors, clients, or other external stakeholders.
• Experience personally soliciting and closing philanthropic gifts or comparable financial commitments.
• Experience managing a portfolio of donors, prospects, clients, or comparable relationships.
• Demonstrated ability to identify and qualify prospective donors and develop relationships that result in increased financial support.
• Understanding of annual and leadership giving, donor cultivation, solicitation, stewardship, retention, and upgrade strategies.
• Strong interpersonal skills and demonstrated ability to establish meaningful relationships with individuals from diverse backgrounds.
• Excellent written and verbal communication skills.
• Strong organizational and project-management skills with the ability to manage multiple priorities and deadlines.
• Ability to work independently, initiate donor outreach, and take ownership of fundraising goals while contributing effectively to a collaborative team.
• Experience using a fundraising CRM or comparable constituent relationship management system.
• Ability to analyze donor information and giving behavior and translate data into actionable fundraising strategies.
• Ability and willingness to travel and attend occasional evening and weekend donor and organizational events.

Preferred

• Experience managing a leadership annual giving, mid-level giving, or similar donor portfolio.
• Demonstrated success securing gifts in the $5,000–$25,000 range.
• Experience qualifying donors from direct response, annual giving, membership, or other broad-based constituent programs.
• Experience developing annual giving societies or donor recognition programs.
• Experience with Raiser’s Edge and familiarity with Raiser’s Edge NXT.
• Experience with moves management and donor qualification practices.
• Experience identifying and transitioning donors into major or planned giving programs.
• Experience soliciting event sponsorships.
• Experience working within a national, chapter-based, membership, museum, education, aviation, military heritage, or other mission-driven organization.
• CFRE certification or interest in pursuing professional fundraising credentials.

Knowledge, Skills and Abilities

The successful candidate will:

• Be comfortable initiating relationships with individuals who may have had little or no previous personal interaction with Development staff.
• Enjoy the process of discovering donor interests, motivations, and philanthropic potential.
• Be comfortable personally asking donors for gifts of $5,000 to $25,000.
• Understand how to move a donor relationship from transactional giving to meaningful philanthropic engagement.
• Recognize that current gift size alone does not determine a donor's future philanthropic potential.
• Demonstrate persistence and sound judgment in prospect qualification and follow-up.
• Balance revenue goals with a commitment to a positive donor experience.
• Be comfortable working toward measurable qualification, solicitation, activity, and revenue goals.
• Use data, donor behavior, and personal engagement to inform fundraising decisions.
• Manage a significant donor portfolio while continually qualifying new prospects.
• Understand leadership annual giving as both an essential source of sustainable revenue and an important pipeline for major and planned gifts.
• Communicate effectively with donors, members, volunteers, Board members, organizational leadership, and colleagues.
• Demonstrate sound judgment, professionalism, discretion, accountability, and respect for donor confidentiality.
• Be enthusiastic about the missions of the Commemorative Air Force and the Henry B. Tippie National Aviation Education Center.

About the Organizations

The Commemorative Air Force is dedicated to educating, inspiring, and honoring through flight and living history experiences. Through its historic aircraft, members, volunteers, educational programs, and events, the CAF brings the stories of American military aviation to life for current and future generations.

The Henry B. Tippie National Aviation Education Center advances this mission through educational experiences and programs that connect aviation history with opportunities for young people to explore aviation, aerospace, STEM, and related career pathways.