Director of Leadership Giving

1. Position Summary

The Director of Leadership Giving is a hybrid frontline fundraising professional responsible for growing philanthropy across a portfolio of major and mid-level donors while leading annual giving strategies that strengthen the organization's donor pipeline.

This role manages a portfolio of major donor prospects and leadership-level donors while overseeing engagement strategies for mid-level donors, annual giving campaigns, and donor pipeline development. The Director of Leadership Giving identifies, cultivates, solicits, and stewards donors whose philanthropic interests align with the organization's mission and strategic priorities.

The position serves as a key connector between annual giving, affinity groups, workplace giving, and major gifts, ensuring donors move through a meaningful engagement pathway that results in increased retention, upgraded giving, and long-term investment in the organization.

The Director of Leadership Giving works collaboratively with marketing, community impact, corporate partnerships, and volunteer engagement teams to create compelling donor experiences and maximize philanthropic revenue.

2. Essential Functions

1. Major Gift Portfolio

   • Qualify and manage a portfolio of approximately 100–150 major donors and prospects.

   • Develop individualized engagement, cultivation, solicitation, and stewardship plans for each donor.

   • Establish annual revenue goals for each portfolio donor based on giving history, philanthropic interests, and capacity.

   • Conduct donor meetings, discovery visits, and stewardship conversations.

   • Develop and present customized proposals, funding opportunities, and gift requests.

   • Partner with program and community impact staff to identify funding opportunities and report donor impact.

   • Secure and close major gifts, multi-year commitments, endowment gifts, and planned gifts when appropriate.

2. Mid-Level Giving Strategy & Portfolio Management

   • Oversee and manage a portfolio of approximately 200 leadership-level and mid-level donors.

   • Develop strategies to retain, upgrade, and deepen engagement among donors giving approximately $500–$1,000 annually.

   • Implement personalized outreach through phone, email, mail, events, and occasional donor visits.

   • Create donor journeys that strengthen relationships and encourage increased philanthropic support.

   • Identify and qualify donors with major gift potential and move them into individualized cultivation strategies.

   • Monitor donor movement and progression through the donor pipeline.

3. Event Integration (Revenue-Focused)

   • Lead the fundraising strategy for donor-focused events, including the annual gala and leadership giving events.

   • Collaborate on sponsorship and table sales strategies.

   • Utilize events as opportunities for donor identification, cultivation, solicitation, and stewardship.

   • Ensure post-event follow-up and donor conversion strategies are executed.

4. Collaboration

   • Marketing for donor communication and storytelling

   • Community impact for funding opportunities and impact reporting

   • Corporate partnerships for shared prospects and sponsorship alignment

5. Data Management & Performance Reporting

   • Maintain accurate donor records and moves management activity within the CRM.

   • Track fundraising progress against revenue and activity goals.

   • Analyze donor trends, retention rates, upgrade opportunities, and campaign performance.

   • Prepare monthly reports and dashboard metrics for leadership.

   • Utilize data to inform fundraising strategy and donor engagement efforts.

3. Key Performance Indicators - KPI's for this position include the following areas of accountability and expected outcomes:

1. Ability to qualify donors from the larger pool of organizational donors that meet the major gift criteria.

2. Ability to create reasonable financial goals for each donor which is based on their giving and their potential

3. Ability to create a personal contact and ask plan, that takes into account the individual donor’s interest, motivations, giving patterns and ask preferences, for each donor on his or her caseload in a timely and cost-effective manner.

4. Ability to retain and upgrade donors.

5. Ability to secure project and organization information and create and write effective offers, proposals and asks. Ability to secure information that can be sent back to donors to report on how their money was used.

6. Ability to create timely reports that reflect caseload performance.

7. Ability to manage people, process, deadlines and budget while adhering to the policies and procedures of the organization.

8. Ability to get along with peers, subordinates and management and maintain a positive and constructive attitude while solving problems. Ability to be a team player and protect the mission, goals and values of the organization.

Required Experience and Education

• 5–7+ years fundraising or relationship-based sales experience

• Knowledge of and experience in planned giving (trusts, bequests, giving through retirement plans, etc.), donor advised funds, estate and financial planning for individuals, and trends in major giving

• Proven track record of securing major gifts and experience closing multi-year gifts

• Strong interpersonal and communication skills

• Experience with CRM systems and moves management

• Experience with proposal writing, prospect research, volunteer management, individual giving campaigns, capital campaigns, donor cultivation and recognition

• Organized with the ability to implement systems and follow-up processes

Statements in this Job Description are intended to describe the general nature of work being performed. They are not intended to be a complete list of all responsibilities, duties and skills required for the position.

Salary Range: $85,000 to $100,000

United Way of Coastal and Western Connecticut includes an excellent benefits package and flexible working arrangements:

1. Paid Time Off – vacation, sick time, 11 paid holidays including 1 floating holiday

2. Paid Family Leave

3. Health Insurance – medical, dental, and vision

4. Life Insurance, short-term disability, long-term disability, and related coverage

5. Hybrid work arrangements

United Way is an equal-opportunity employer and seeks to hire staff members who reflect the diversity of the communities we serve. All positions are filled without regard to race, color, religion, sex, national origin, age, sexual orientation, gender identity or expression, disability, employment status, veteran status, or any other characteristic protected by law. If much of this job describes you, please apply. Research shows that women and people from underrepresented groups often apply to jobs only if they meet all qualifications. We recognize this and encourage those with relevant skills and experience to apply.