Director, Individual Giving (Boston)

Road Scholar

Boston, MA 02114

United States

Posted July 6, 2025

{FULL_TIME,VOLUNTEER,TEMPORARY,PART_TIME}

Valid until August 5, 2025

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Job Description

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When it comes to creating educational travel adventures that enrich the lives and fulfill the dreams of more than 100,000 people every year, there's no organization better than Road Scholar. What's our secret? Dedicated and talented staff who believe in our mission.
At Road Scholar, we are committed to fostering a culture of inclusivity and belonging. We believe that by valuing a wide range of perspectives and experiences, we create a stronger, more innovative organization that reflects the communities we serve.
In addition, we are dedicated to bringing an environmentally sustainable organization. From the way we design our programs to how we operate as a team, we are striving to reduce our environmental impact and create a positive legacy for future generations.
About The Role…
The Director of Individual Giving plays an integral role in the organization’s overall goals for revenue and donor engagement and is responsible for managing and helping to grow the individual mid-level, major and planned giving programs. The Director will manage a small team and maintain a portfolio of 50+ prospects and donors to steward and solicit for annual support. This position currently reports to an interim department leadership structure and will work closely with several part-time volunteer fundraisers and the marketing and communications teams who manage the direct response fundraising program.
Road Scholar offers a remote work environment. The compensation range for this exempt level salaried position is $90,000.00 - $100,000.00 based on experience.
In this role, you will...

Manage department team which currently consists of one Senior Coordinator and several part-time volunteer front line fundraisers.
Maintain and steward a portfolio of 50+ prospects and donors to generate support for Road Scholar and meet revenue and established goals.
Develop and execute strategies for each portfolio prospect and donor to move them through the gift cycle.
Support the writing, editing and preparation of planned and major gift communications and marketing in coordination with the Marketing and Creative teams.
Manage the maintenance of the planned giving database and coordinate with Finance on life income payments and regular reporting.
Together with the Finance team, coordinate administration of administer bequests to Road Scholar.
Responsible for the leadership, major and planned giving lead process for the department.
Own the correspondence, acknowledgements, stewardship, and communications processes for the department, working in concert with Senior Coordinator and others within Road Scholar.
Reconcile monthly revenue and expenses with Finance dept and make quarterly budget reprojections as requested.
Maintain accurate records by diligently tracking prospect and donor contact, status, and next steps in a donor relationship management database.
Special projects and other responsibilities as needed.

We're seeking...

5-7 years fundraising experience, with at least 2-3 years of frontline gift officer experience, staff management and direct planned giving exposure.
Experience with mid-level giving and a proven track record of securing four and five-figure gifts.
Special training in Planned Giving; ongoing seminars/workshops in Planned and Major Gifts. Knowledge of basic estate planning, life income vehicles and federal tax law regarding charitable giving.
Good quantitative skills: understanding of basic accounting or finance a plus.
Proven experience with independently managing a portfolio and the ability to build long-term relationships with donors; commitment to donor confidentiality.
Excellent interpersonal and communication skills are essential, both written and verbal.
Must be able to represent Road Scholar to potential donors and make compelling presentations and requests for support.
Must be a self-motivated professional, with energy and persistence, willing to be hands-on with the ability to work independently and as part of a small, collegial team.
Must have a high level of computer proficiency in standard business software including Microsoft Office applications (Outlook, Word, Power Point, and Excel). Experience working with fundraising databases required; experience with PGCalc and Salesforce a plus.
Commitment to the Road Scholar mission of learning, discovery and travel and a desire to work with older adults.
Willingness to travel as needed and ability to attend activities outside of normal work hours, with advanced notice. Travel no more than 20%.

For serious consideration, please submit a cover letter along with your resume. Your cover letter should include your salary requirements and telling us why you're interested in the position.
Why join the Road Scholar Team...
We offer a competitive compensation and benefits package!

Medical, Dental and Vision Insurance (with a substantial employee subsidy!)
403(b) Retirement Plan with a company match of 5% after 1 year of employment!
Up to 20 days of PTO annually, accrued every payroll cycle
Enjoy a paid week off, in addition to your PTO, at the end of December to enjoy the holiday season!
A generous employee discounts on our programs
Access to obtain a Care.com membership
As a Road Scholar employee, you can opt-in to receive an IATA membership
We take professional development seriously which is why we provide LinkedIn Learning access to all employees amongst other professional development opportunities
That’s right, we’re fully remote!
To learn more about our benefits offerings, check us out at

Equal Opportunity Employer
Road Scholar supports diversity in our staff, participants, and programs. An Equal Opportunity Employer Road Scholar values and supports individual differences and strives to create an environment that contributes to the success of both the individual and the organization. As an Equal Opportunity Employer, we consider applicants for all positions without regard to race, color, religion, gender, national origin, age, sexual orientation, pregnancy, illness, marital or veteran status or disability or any other status protected by applicable law.
Cybersecurity
At Road Scholar, we are committed to cybersecurity and to providing a safe experience for job seekers. All official communication regarding employment opportunities will come exclusively via email from the official Road Scholar domain or from our applicant tracking system URL recruiting.ultipro.com. We never conduct interviews through texting applications or instant messaging platforms. If you receive an employment offer or other correspondence from an individual at Road Scholar you have not met, or from a non-Road Scholar email domain, it may be a phishing attempt.