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Class 8 Trailer Sales Executive

Job Description - Class 8 Trailer Sales Executive

Class 8 Trailer Sales Executive

Location: Caledonia, WI
Territory: Eastern Wisconsin and Greater Chicago

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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