Senior Director of Development & Major Gifts

The Position

Reporting to the Executive Director and serving as an important member of the executive leadership team, the Senior Director of Development & Major Gifts leads Island Senior Resources’ comprehensive contributed revenue program and serves as the organization’s lead frontline fundraiser. Working closely with the Executive Director, Board members, and other organizational leaders, and overseeing the work of the Director of Annual Giving, the Senior Director will spend the majority of their time directly engaging donors through visits, conversations, proposals, solicitations, and stewardship while providing strategic direction for the broader development program. This position represents an important evolution in ISR’s approach to philanthropy. Building upon a strong annual giving foundation, the Senior Director will help ISR intentionally expand major giving.

A primary focus will be strategically managing a portfolio of major donors and prospects, expanding that portfolio over time, and developing individualized cultivation, solicitation, and stewardship strategies.

The Senior Director will lead the formation and annual refinement of a written development plan, establish revenue goals and performance measures, monitor donor retention and movement through the development pipeline, and ensure disciplined use of ISR’s donor management system for moves management, documentation, forecasting, and reporting. The position will also help translate ISR’s programs, financial position, and community impact into a compelling case for support.

Working collaboratively across ISR, the Senior Director will partner with the Executive Director on key donor relationships and strategic asks; engage Board members in cultivation and stewardship; supervise and coach development staff; collaborate with communications, community engagement, finance, and program staff; and support donor gatherings, tours, cultivation activities, and special events. The position will help strengthen an organization-wide culture of philanthropy while ensuring development efforts remain transparent, accountable, and aligned with ISR’s mission and strategic priorities.

The Ideal Candidate

Island Senior Resources is seeking an accomplished fundraising professional who understands that successful development is built on relationships, trust, and connecting donor interests with meaningful organizational impact. The ideal candidate will bring a proven record of major gift fundraising and donor management.

The successful candidate will be both a strategist and a hands-on fundraiser, comfortable managing a major donor portfolio, building individualized cultivation strategies, making meaningful asks, and stewarding relationships over time. This person will use donor history, retention information, data, and moves management to guide decisions while recognizing opportunities for estate gifts, retirement assets, securities, real estate, donor-advised funds, and other planned or asset-based giving. A thoughtful, disciplined approach to donor engagement and follow-through will be essential.

Equally important will be the ability to succeed within a collaborative, community-based organization. The ideal candidate will be a strong team player and relationship builder who works effectively with the Executive Director, Board, staff, volunteers, donors, and community partners.

This person will bring accountability, strong documentation practices, transparency, follow-through, sensitivity to equity and inclusion, and local knowledge or the ability to build meaningful community connections. ISR is looking for someone with a growth mindset, humility, humor, sound judgment, and a genuine heart for the mission.

Education & Experience

A minimum of five (5) years of progressive fundraising experience, including demonstrated success in individual and major giving, is required, with ten (10) years of experience preferred. Eight (8) or more years of fundraising experience, including at least three (3) years with senior development responsibilities, is also preferred. Candidates must demonstrate the ability to build donor trust and personally cultivate, solicit, and close significant gifts, ideally within a small or mid-sized nonprofit environment.

Experience developing and implementing a comprehensive development plan across multiple revenue streams, managing a major donor portfolio, using donor database/CRM and moves-management systems, establishing fundraising metrics, forecasting contributed revenue, and partnering with executive leadership and Board members is highly desirable. Experience supervising or mentoring development staff is also preferred.

A record of success supporting a capital or special campaign, experience with planned and legacy giving, and an event-management background are strongly desired. Experience with a nonprofit serving older adults, people with disabilities, human services, or a similarly mission-driven organization is preferred. CFRE certification or the ability to achieve certification within the first 12 months of employment, is preferred.

ISR is principally seeking demonstrated fundraising expertise, results, judgment, relationship-building ability, and the capacity to successfully lead a sophisticated major gifts and development program. Necessary Knowledge, Skills, and Abilities:

• Demonstrated knowledge of major gift fundraising, donor cultivation, solicitation, stewardship, moves management, and long-term relationship development.
• The ability to strategically manage a portfolio of major donors and prospects, develop individualized strategies, and maintain consistent, meaningful donor contact.
• Knowledge of the progression from annual giving to major gifts, capital and special campaigns, and planned or legacy giving, including estate gifts, retirement assets, securities, real estate, donor-advised funds, and other non-cash giving opportunities.
• Strong nonprofit financial literacy, including the ability to understand financial statements, revenue sources, IRS Form 990 information, fundraising trends, donor retention, and organizational inputs, outputs, and outcomes.
• The ability to translate ISR’s programs, finances, strategic priorities, and measurable impact into compelling donor communications and cases for support.
• Demonstrated skill in developing and implementing comprehensive development plans, establishing revenue goals and metrics, forecasting contributed revenue, and evaluating performance.
• Strong donor database and CRM skills, including disciplined moves management, donor documentation, portfolio tracking, and reporting.
• Demonstrated ability to cultivate donor trust and personally solicit and close significant gifts, including four- and five-figure gifts and above.
• Skill in partnering with executive leadership and Board members on donor cultivation, strategic asks, introductions, and stewardship.
• Strong leadership and supervisory skills, including the ability to coach staff, establish expectations, strengthen accountability, and support an integrated development program.
• Excellent written, verbal, interpersonal, presentation, storytelling, organizational, and event-management skills.
• The ability to work independently and collaboratively with strong judgment, discretion, integrity, transparency, accountability, and sensitivity when handling confidential donor information.

Compensation & Benefits

• $135,000 - $140,000 DOQ
• Work Schedule: Hybrid - This position offers flexible work arrangement, with a combination of remote work and in-person work at our office. Specific in-office days and remote work arrangements will be determined based on organizational needs and team collaboration.
• Vacation - 12 days of vacation accrued per year (increasing to 20 days per year by 5 years).
• Paid Holidays - 11 federal holidays with full office closure plus 1 anniversary holiday per year.
• Sick Leave - 12 days per year.
• Paid leave for Bereavement and Jury Duty
• Health Insurance - Employer-paid Health Insurance for the employee with buy-up options available; employee-paid options are available for dependents. Employees who opt out of the group plan because they have other minimum essential coverage may be issued cash up to $420 per month.
• Vision Insurance - Employer-paid Vision Insurance for the employee; employee-paid options are available for dependents.
• Group Term Life and Accidental Death and Dismemberment (AD&D) Insurance - up to a $10,000 benefit.
• Employee Assistance Program.
• Optional 401K.
• Relocation Assistance.