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