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Class 8 Trailer Sales Executive
Position Overview
The Class 8 Trailer Sales Executive will develop new business and manage commercial equipment relationships throughout Eastern Wisconsin and the Greater Chicago market.
This is a full-cycle outside sales role responsible for prospecting, customer development, equipment consultation, quoting, negotiation, financing coordination, delivery, and post-sale relationship management.
The Sales Executive will represent multiple trailer product lines and sell, rent, and lease new and used commercial trailers to private fleets, trucking companies, owner-operators, contractors, manufacturers, distributors, and industrial organizations.
Key Responsibilities
Develop new trailer sales, rental, and leasing business throughout the assigned territory
Prospect private fleets, trucking companies, owner-operators, contractors, manufacturers, distributors, and commercial equipment users
Generate opportunities through cold calling, email outreach, referrals, customer visits, online research, trade shows, and industry events
Build and maintain long-term relationships with new and existing customer accounts
Sell new and used commercial trailers across multiple product lines
Promote rentals, leasing, financing, parts, service, modifications, and equipment upgrades
Evaluate customer requirements including freight type, payload, axle configuration, operating environment, replacement schedule, and budget
Recommend appropriate trailer models, configurations, options, and service packages
Prepare accurate quotes, proposals, orders, contracts, and sales documentation
Negotiate pricing and commercial terms within approved guidelines
Coordinate equipment demonstrations, inspections, and customer evaluations
Manage equipment delivery, titles, bills of sale, plates, inspections, and customer acceptance
Work with Parts and Service teams to coordinate modifications, maintenance, repairs, and add-ons
Maintain accurate CRM records, prospect activity, quotes, contracts, and pipeline information
Follow up consistently with active prospects and existing customers
Resolve customer concerns involving equipment condition, delivery, documentation, maintenance, or service
Attend manufacturer training, regional exhibits, customer events, and industry trade shows
Monitor competitor activity, pricing, product availability, and market trends
Meet established sales goals for prospecting, customer meetings, proposals, revenue, and gross profit
Provide accurate sales forecasts and activity reports to leadership
Requirements
3+ years of business-to-business sales experience
Proven ability to prospect and develop new customer accounts
Strong cold-calling, relationship-building, negotiation, and closing skills
Ability to manage and grow an assigned territory and customer portfolio
Strong written communication and presentation skills
Excellent organization, time management, and follow-up abilities
Ability to work independently and manage multiple sales opportunities
Proficiency with Microsoft Outlook, Word, Excel, PowerPoint, and CRM systems
Basic understanding of pricing, gross margin, revenue, and sales performance metrics
Valid driver's license
Ability to travel frequently throughout Eastern Wisconsin and Greater Chicago
Willingness to attend occasional overnight meetings, training programs, or trade shows
Preferred Qualifications
Experience selling trailers, trucks, heavy equipment, construction equipment, agricultural equipment, or transportation services
Background in commercial equipment rentals, leasing, financing, or dealership sales
Existing relationships with trucking companies, private fleets, contractors, manufacturers, or industrial customers
Knowledge of Class 8 trucks, semi-trailers, axle configurations, payload requirements, and equipment applications
Experience selling flatbed, dump, tanker, specialized, or open-deck equipment
Experience coordinating equipment modifications, delivery, title documentation, and post-sale service
Bachelor's degree in Business, Sales, Transportation, Marketing, or a related field
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