Director of Alumni Engagement and Annual Giving

Florida, United States
Competitive Salary
Apr 26, 2021
May 25, 2021
Employment Type
Full Time


The Bolles School, a Northeast Florida  independent college preparatory day and boarding school founded in 1933, has long been known as one of the top educational institutions in the country. This prominence is rooted in an enduring " All Things Possible" mindset that encourages students to discover their strengths and excel in them, throughout the Bolles experience.  The Bolles School motto is ' pursuing excellence through integrity , courage and compassion'. 



The Director of Alumni Engagement and Annual Giving will implement a comprehensive plan for the Bolles Alumni Association including cultivation and stewardship efforts that results in higher participation rates of engaged and involved alumni and increased giving through the annual fund, major gifts, capital campaigns and planned gifts in alignment with strategic fundraising priorities. 


The objective of all alumni in-person and virtual events is cultivation resulting in annual gifts to the school as well as the identification of prospects for other gifts as mentioned above, referring to the CAO for strategy and further assignment to the Major Gifts Officers. This position works closely with Department Chairs, faculty, staff, and the Advancement Team to maximize cultivation of the best prospects among various alumni constituencies. 




  • Bachelor’s degree required; Master’s degree or CFRE preferred.
  • Related experience in a similar not-for-profit program environment, preferably education desired.
  • High degree of initiative along with strong organizational skills.
  • Seasoned in fundraising principles and strategies.
  • Demonstrated success in stewarding donors strategically resulting in a contact and cultivation plan that values past and current donors and focus on the school’s alumni.
  • Demonstrated success closing major level gift solicitations preferred.
  • Ability to read and interpret documents, write routine reports, and write first-class donor letters and acknowledgements that demonstrate a working knowledge of writing for philanthropy in all correspondence desired.
  • Ability to work collaboratively with all constituents.
  • Demonstrated proficiency with internet functions and ability to adapt to new software applications.
  • High professional and ethical standards in handling confidential information.
  • Ability to organize and complete multiple tasks with close attention to detail and deadlines.
  • Excellent communication, listening, and interpersonal skills.
  • Ability to think and plan strategically and creatively.
  • Must be willing to work extended hours and travel as needed.
  • A high level of professionalism in character, appearance, and demeanor.
  • Ability to communicate and collaborate effectively with school administration, parents, alumni, faculty, and staff.
  • Demonstrate high competency with Raiser’s Edge NXT, especially for relationship management and moves management.
  • Be primary alumni fundraiser for The Bolles School.



  • Must demonstrate and enthusiastically support the School’s Mission.
  • Willingness to perform in a manner that reflects positively on The Bolles School.
  • Must have the ability and willingness to communicate well, work congenially, and deal effectively with all school personnel and school families, as well as with the larger business and educational community.


Essential Functions:


  • Work with the Director of The Bolles Annual Fund and Parent Programing to meet short and long-range fundraising goals and participation objectives.
  • Establish alumni class annual gift goals.
  • Manage the alumni volunteer programs and plan all events that relate to alumni fundraising.
  • Seek out innovative methods to increase giving and efficiencies through professional development opportunities and networking with peers at other independent schools.
  • Create excellent written communication weekly or on various schedules throughout the year that involve and engage the various alumni constituencies with The Bolles School.
  • Create virtual and in-person reunion opportunities for alumni with proven marketing methods that will cultivate the various alumni groups.
  • Manage an interactive online community.
  • Establish annual class giving models, annual virtual & in person socials, and annual appeals.
  • Establish alumni networking programs and regional chapters in key regions. Plan effective agendas for those chapters and annual objectives for cultivation and communication.
  • Responsible for continually updating alumni information on the website and the giving form to assure that they are functional and up to date for those who wish to give electronically.
  • Establish processes with other key advancement team members to assure that donor gifts are recorded and acknowledged properly and that the end beneficiary such as departments within The Bolles School are advised of the gifts and the requirements, obligations, and deadlines for use. These processes need to be in writing as a part of the operations of the Advancement department.
  • Works with members of the school community, including various departments, faculty, and staff to implement a plan of alumni cultivation, giving, and stewardship with the assistance of the Stewardship and Alumni Officer.
  • Continually assess and develop a comprehensive plan with the Stewardship and Alumni Officer to thank, acknowledge, engage, and involve alumni in The Bolles School family.
  • Create meaningful experiences for alumni based on donor research and knowledge.
  • Must be able to engage alumni leaders and oversee the management of the Alumni Association Program & Portal, Board of Visitors, and Alumni Board through organizational skills and meaningful programs and agendas.
  • Must be excellent at follow up and responsiveness to alumni requests and needs. 
  • Provide the CAO with annual goals and objectives with strategies reviewed on a quarterly basis.
  • Collaborate with the Advancement Team for the purpose of securing annual and major gifts.
  • Must work in conjunction with the Stewardship and Alumni Officer to organize all research reporting for the stewardship of alumni donors.
  • Cultivate donor relationships using best practices and professional standards in every donor engagement.
  • Must create a top 50 alumni list which is ever evolving with individualized and customized stewardship plans in conjunction with the Stewardship and Alumni Officer, CAO and the Leadership Gift Officers.
  • Develop and implement alumni events in collaboration with the Advancement Team.
  • Maintain a working knowledge of all naming opportunities for Capital Campaign gifts, as well as long term and short-term needs that benefit from philanthropy.
  • Work with the Stewardship and Alumni Officer in preparing stewardship materials and correspondence within the best practice guidelines for writing for philanthropy.
  • Produce thought driven proposals based on alumni/donor interests.
  • Responsible for a complete communications plan for all alumni, with the approval of the CAO.
  • Designs and drafts gift proposals and funding options in collaboration with the CAO and Communications Department.
  • Prepares and provides reports to the Director of Advancement Services and Advancement Services Coordinator to properly register gift proposals, gift agreements and gift income.
  • As a member of the Bolles Advancement Team, performs other duties as requested by the CAO.