Director of Major Gifts and Leadership Giving

The Trinity-Pawling School is a leading independent all-boys boarding school with a close-knit community of 100 employees and 300 students.  Our activities and efforts are focused on our mission, which is to educate and instill a value system that prepares young men to be contributing members of society amidst the challenges of the ever-changing world.  Currently, we are seeking a Director of Major Gifts and Leadership Giving.

The Director of Major Gifts and Leadership Giving reports to the Director of Advancement and works closely with Advancement and Trinity-Pawling School leadership to develop and implement a comprehensive strategy for a robust major/leadership gifts and planned giving program, and oversee Alumni, Parent, and Family giving and engagement, as well as the Trinity-Pawling Fund, in support of Trinity-Pawling School’s mission, vision, and strategic goals.

Essential Duties

• Support the Director of Advancement and Trinity-Pawling School leadership in strategic planning and revenue forecasting by executing plans in support of individual and team fundraising benchmarks aligned with the School’s mission, vision, and strategic goals.
• Identify, research, qualify, categorize, cultivate, solicit, and steward current and prospective donors of major/leadership gifts, planned gifts, integrated gifts, and future campaign/transformational gifts and pledges through fundraising best practices and strategies.
• Lead and mentor a growing team of frontline fundraisers responsible for alumni/reunion giving, parent/family giving, and the Trinity-Pawling Fund, and recruit volunteers as necessary.
• Maintain and increase donor engagement, and secure major, leadership, and planned gifts through personalized correspondence, in-person visits, telephone/video calls, concept briefs, proposals, presentations, and/or other relationship-building methods.
• Manage a portfolio of prospects including alumni, parents, family members, trustees, community members, and other stakeholders of the School.
• Ensure achievement of fundraising goals, moving donors along the prospect pipeline, deepening relationships to better understand and strategically align donors’ priorities and goals with the needs of the School, and growing a culture of philanthropy among the School’s networks.
• Solicit gifts for building renovation/construction, naming opportunities, endowment, programs, scholarships, legacy initiatives, annual funds, unrestricted support, or other initiatives identified as a priority by the School.
• Improve efficiency by analyzing data in collaboration with Advancement team staff (e.g., donor pool, response rates, ROI, etc.); establishing goals by using benchmarking data and best practices from peer institutions; analyzing demographic and psychographic trends; and creating reports from the School’s database.
• Establish clear metrics for success, track progress to goal, and adjust strategy as required.
• Develop personal mastery by participating in professional development, reading professional publications, and networking to incorporate best practices and innovative fundraising strategies.
• Promote the interest of students by being a good role model, establishing and reinforcing clear boundaries and guidelines, encouraging students’ autonomy and independence and acting in a transparent manner.
• Perform other duties as may be required.

 Position Requirements

Bachelor’s degree required with at least 8 years of progressive experience in frontline fundraising, with a minimum of 5 years in major gift fundraising, demonstrated success with soliciting and securing 6+ figure gifts/pledges, and supervisory experience. Familiarity with education and/or fundraising in an independent school environment is preferred.  The qualified candidate will also possess:

• social skills, a sense of humor, flexibility, dependability, high energy, creativity, entrepreneurialism, analytical and problem-solving skills, self-motivation, sound judgement, high ethical standards, collegiality, and the ability to work effectively with a team;
• excellent writing, editing, proofreading, and communications skills, meticulous attention to detail, and eloquent prose, in forms ranging from casual emails to information-laden concept briefs, reports, or proposals.

 And be able to:

• successfully manage all aspects of the giving cycle, employ moves management strategies, and establish/build relationships with top-level donors, trustees, and other high net worth prospects
• make in-person major and planned gift solicitations, as well as assisting the Director of Advancement, trustees, and others with solicitations
• conduct timely and appropriate follow-up, successfully close major and planned gifts, and achieve or exceed fundraising goals
• analyze donors’ propensity, capacity, and enthusiasm to give, and ensure donor alignment
• communicate effectively the various planned giving vehicles and tax implications to donors and their advisors
• positively motivate, mentor, manage, and lead a growing team of fundraising professionals toward program ownership, vision thinking, and goals achievement, and effectively delegate work
• create, plan, implement, and manage multiple and concurrent projects and events
• build cross-functional partnerships
• leverage technology by extracting data to create documents, spreadsheets, presentations, and reports using software such as Word, Excel, PowerPoint, Outlook, Teams, Google products, Raiser’s Edge, etc.
• participate in evening and weekend activities and able to travel both domestically and internationally
• meet the physical demands which include sitting for prolonged periods of time at a desk or computer workstation, using repetitive arm, hand and finger movements traveling on uneven terrain, climb/descend stairs/stand for long periods of time and carry up to 50 pounds.

Note:  Trinity-Pawling School is mandating that all eligible employees are vaccinated against Covid-19.

Interested candidates should apply by visiting our Career Site.  All applications need to include a resume, cover letter and writing sample.

 Trinity-Pawling School offers all full-time employees a comprehensive benefit plan which includes medical, dental, retirement, and paid time off as well as the use of our state-of-the-art facilities. 

 The Trinity-Pawling School provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability or genetics. In addition to federal law requirements, the School complies with applicable state and local laws governing nondiscrimination in employment.  Employment is contingent on candidates receiving a satisfactory criminal background check.