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