Sales Associate-Guide

Wheelzup Adventures; Cumberland (MD); On-site; USD 2,066,000 - 3,031,000; Full time

Job summary

Wheelzup Adventures in Cumberland, MD, is seeking a high-energy Seasonal Guide to help customers find the best gear, bikes, and experiences for their outdoor adventures.

The role blends customer service with product expertise, requiring friendly, proactive individuals who thrive in a fast-paced retail outdoors setting and want to balance summer work with winter travel or other adventures.

Qualifications

• Warm, friendly, professional customer service.
• Ability to lift 40 lbs and stand for extended periods.
• Outfitting customers for bike and water rentals (training provided).
• Learn and use Google Workspace and retail systems (Square, Peeks).
• Commit to Trek U training and Wheelzup’s internal service training.

Responsibilities

• Welcome and guide customers to the right products and services.
• Ask questions to understand customer needs.
• Achieve sales goals through service and product knowledge.
• Promote Wheelzup programs like Season Pass, events, rentals.
• Set up and outfit rentals; ensure safety briefings.
• Process purchases, returns, and event registrations.
• Maintain displays and assist with inventory.

Skills

Customer service

Sales

Outdoor enthusiasm

Reliability

Education

High school diploma or equivalent

Tools

Square POS

Peeks

Google Workspace

Job description

Wheelzup Adventures - Cumberland, MD
Seasonal Full-Time (March-October) | Ideal for Winter Travelers

SUMMARY

At Wheelzup, we don’t have “salespeople” - we have Guides. A Guide’s mission is to help people choose the right gear, apparel, bikes, and experiences so they can have their best possible adventure outdoors.

This role blends customer service, product expertise, and outdoor enthusiasm with the ability to generate strong retail sales. The most successful Guides are friendly, curious, proactive, and committed to helping customers find the products or services that truly fit their needs.

This is a seasonal, high-energy role perfect for someone who wants to work hard during the spring-summer-fall and pursue travel, skiing, or other adventures during the winter.

KEY RESPONSIBILITIES

• Welcome, assist, and “guide” customers to the right products, bikes, apparel, and services.
• Build trust by asking good questions and listening to customer needs.
• Achieve sales goals through exceptional service, product knowledge, and proactive engagement.
• Promote Wheelzup programs, including the Season Pass, events, rentals, and local adventures.

Rentals & Outfitting

• Set up and outfit walk-up and scheduled bike/kayak/SUP rentals.
• Ensure customers are fitted properly, briefed on safety, and confident before heading out.
• In a pinch, complete a rental or shuttle booking using the reservation systems.

Store Operations

• Process purchases, returns, special orders, and event registrations.
• Maintain clean, stocked, and visually appealing retail displays.
• Help with receiving product shipments and organizing inventory areas.
• Resolve customer questions, concerns, or issues with professionalism and care.

Brand Representation

• Represent Wheelzup’s mission of Access, Knowledge, and Community.
• Offer accurate information about trails, bikes, outdoor brands, and local activities.
• Maintain a positive, welcoming atmosphere for customers, partners, and visitors.

QUALIFICATIONS

Required

• Warm, friendly, professional customer service skills.
• Ability to lift 40 lbs, stand for extended periods, and work indoors/outdoors.
• Comfort outfitting customers for bike and water rentals (training provided).
• Ability to learn and use Google Workspace and retail systems (Square, Peeks).
• Commitment to completing Trek U training and Wheelzup’s internal service training.

Preferred

• Knowledge of outdoor brands (Patagonia, Kuhl, Altra, Salomon, etc.).

WORK SCHEDULE

• March-October: Full-time, active, customer-facing season.
  Expect weekends, busy days, and steady outdoor engagement.
• November-February: The perfect time for seasonal staff to pursue other adventures -skiing, traveling, exploring, or focusing on personal passions.

WHO THRIVES IN THIS ROLE

This job is perfect for someone who:

• Loves the outdoors and enjoys helping people get outside.
• Wants a job where sales happen naturally through great guidance and conversation.
• Enjoys working in a small, values-driven team.
• Is energetic, reliable, and motivated by seeing happy customers.
• Wants a lifestyle that allows intense summer work and freedom during the winter.

ABOUT WHEELZUP

Wheelzup Adventures is a mission-driven outdoor hub dedicated to helping people have their best experience outdoors. We combine retail, rentals, shuttles, and guided experiences to support our pillars: Access, Knowledge, and Community.