Group Leader (Charlottesville, VA and Williamsburg, VA)

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 most consequential element of any Road Scholar program is the Group Leader. As the foundation and often only consistent variable of the program experience, the Group Leader performance drives the quality of the program. Ultimately, the primary role of a Road Scholar Group leader is to ensure the group experiences all program elements in a fluid, meaningful, and enjoyable way. From beginning to end, the Group Leader oversees all essential academic and non-academic features. The Group Leader is expected to support with delivering educational talks and experiences and tying together the overall theme of the program.

This is a part-time/seasonal opportunity for various programs throughout Virginia. Due to the seasonal nature of the role, this position is not benefits eligible. Hourly rates vary based on program location which ranges from $15.00 to $23.00 per hour plus tips. CTD certification required or extensive professional tourism experience.

We are seeking Group Leaders who live in the program destination/region or has an intimate knowledge of the destination.

Specific Programs:

• • Charlottesville 9113: Three Friends: Thomas Jefferson, James Madison, James Monroe (10/12/2025 - 10/15/2025)
  • Charlottesville 19969: Virginia, Mother of Presidents: Seven Historic Sites (10/5/2025 - 10/10/2025)

The following are the main responsibilities (additional duties may be assigned by Road Scholar):

In this role, you will...

Pre-Program Responsibilities:

• Prior to the program start date, the Group Leader and Road Scholar will hold a pre-program briefing

• Review PIFs (Participant Information Forms) and relevant Program Information
• Send Pre Program Email to participants (optional)

On-Site Program Responsibilities:

• Lead and manage all logistics and responsible for supporting educational delivery and quality including but not limited to:
• Airport meet & greet (when transfer is included); facilitate hotel check-in and registration.
• Reconfirm vendors & included activities (instructors, local guides, coach, restaurants, etc.).
• Conduct Orientation and Farewell Briefings and Daily Wrap-up Briefings
• Listening Device Management.
• Accompany participants to all scheduled program activities and be available 24-7.
• Enhance “free time” opportunities through providing suggestions and organize group dining opportunities.
• Liaise with local guides and instructors to ensure content is presented in a clear and relevant manner and to drive Q&A and educational impact with participants.
• Disbursement of payment to vendors (including tips) and manage program budget.
• Anticipate and resolve program issues on site. Issues to include participant attitude, mobility concerns, dietary restrictions, vendor cancellations, missed activities, weather events. This should be done in close liaison with Road Scholar.
• Follow established emergency procedures and elevate issues to Road Scholar as necessary.
• Adhere to Road Scholar branding guidelines regarding use of Road Scholar apparel & signage.

We're seeking...

• Group leadership experience in an educational and/or travel program environment; prior Elderhostel/Road Scholar experience preferred as well as experience working with individuals 55 and handling different levels of physical ability preferred.
• Bachelor’s degree or relevant experience strongly preferred.
• Preferably lives in the program destination/region or has an intimate knowledge of the destination.
• Strong leadership skills to build group cohesion.
• Sets clear expectations to participants.
• Empowered to enhance impact of educational experiences.
• Excellent organizational, problem-solving.
• Strong communication skills and excellent command of English.
• Ability to work with a team and collaborate and share best practices.
• Should be capable of operating basic AV functions (setting up laptop/projector for lectures).
• Have access to reliable cell phone, capable of texting and/or emails. Road Scholar cannot require Group Leaders to have a Smart Phone, or similar, but it is our expectation that your cell phone has these capabilities.

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.