Route Jump Driver (Richmond)

Trolley House Refreshments is the convenience services division of Trolley Hospitality Companies, a Richmond-based hospitality group serving the greater Richmond and Hampton Roads regions. We deliver customized snack, beverage, and fresh food solutions to offices, hotels, and public venues through modern vending and micro-market services. Our commitment to quality extends beyond the food—we believe our success starts with our people. Driven by a shared purpose of delivering happiness to our customers, community, and team, we focus on fostering a supportive and positive workplace where everyone's contributions are valued.

About the role

As a jump driver, you will support different levels of route drivers in various environments, including hospitals, schools, jails, state offices, corporate offices, industrial facilities, manufacturing facilities, and laboratory facilities. Each day may involve a different route.

• Maintain working, well-stocked, and clean vending machines, micro-markets, and/or coffee/water services on a variety of routes, serving as the core resilience team covering vacations, absences, new market openings, and filling in route stops that need extra attention.
• Enhance customer relations through professional and friendly customer service.
• Address customer needs and requests promptly and respond to customer complaints as they arise.
• Accurately record inventory information to relay back to the warehouse.
• Be resourceful and proactive in dealing with issues that may arise.

Requirements

• Valid driver's license (standard operator's license, CDL not required) – REAL ID required. If not currently in possession, one must be acquired in the first four weeks of employment.
• Minimum of five (5) years of safe driving experience.
• Previous route driving experience in vending or similar highly preferred.
• Inventory or merchandising experience highly preferred.
• Experience using smartphones and apps.
• Experience in detail cleaning food-related machinery to sanitary levels.
• Excellent customer service skills.

Qualities we value

• You are a morning person and like to start your day before the sun rises.
• You plan ahead for weather and stay warm and dry by being prepared.
• You are a quick mover and like to get things done efficiently.
• You seek out opportunities to "leave it better than you found it."
• Providing excellent customer service brings you joy.
• You understand the importance of meeting deadlines and commitments.
• You have a natural knack for apps and working digitally.
• You are willing to own your mistakes and learn from them.
• You understand that working independently and teamwork go hand-in-hand.

Our Values – The Trolley Way

• No excuses
• Do the right thing
• Can-do attitude
• Always growing
• Help first—be part of the solution
• Transparency and honesty—no BS

Pay

• $900 per week during training.
• After 60-90 days and completion of route coverage, pay changes to 6% average of total sales.

Schedule

Monday–Friday, 5:00 AM until the job is complete (usually 1:00 PM–3:00 PM). Rotating Saturdays every 16 weeks.

Benefits

• Company-paid holidays, vacation time, and floating holidays.
• Medical, dental, and vision insurance plans available.
• 401(K) retirement plan and company match after one year of employment.
• Company-paid life insurance and short-term disability.
• Employee Assistance Program (EAP).
• Gym membership discounts.
• Free employee shift meal.
• Discounts at all Trolley House Hospitality companies, including catering services and vending items in our warehouse.

Winner of Richmond 2026 Top Workplaces Award.