Route Driver (Chesapeake)

Trolley Hospitality Companies•Chesapeake, VA
•Onsite

About The Position

Winner of Hampton Roads 2026 Top Workplaces Award 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. We hope you will join us!

Requirements

  • Valid driver's license (standard operator's license, CDL not required)
  • Minimum of five (5) years safe driving experience
  • Previous route driving experience in vending or similar highly preferred
  • Inventory or merchandising experience highly preferred
  • Experience using smart phones and apps
  • Excellent customer service skills
  • Ability to work early morning hours starting at 5am, Monday thru Friday ( Rotating Weekend Schedule )
  • Must be able to lift products up to 50 pounds, while loading and unloading a truck

Responsibilities

  • Maintain working, well stocked, and clean vending machines, Micro Markets, and/or coffee/water services on a fixed route.
  • Enhance customer relations through professional and friendly customer service.
  • Visit key accounts regularly and 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.

Benefits

  • $900 weekly (while in training)
  • Commission based on built route sales, after training completion
  • Company paid Holidays, Vacation time, & Floating Holidays
  • Medical, Dental, and Vision insurance plans available
  • 401(K) retirement plan and company match after 1 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
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