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Trailer Sales Executive

GoodwinRecruitingMilwaukee, WI🇺🇸United States

Why this role stands out

Take ownership of your professional trajectory in this high-impact sales role, where you will enjoy the autonomy to grow your territory while benefiting from a competitive base salary and uncapped commission potential. You will thrive here if you are a driven industry expert who loves building long-term fleet relationships and values the flexibility of a hybrid work environment. Apply today to accelerate your career with a supportive team that rewards your success and provides excellent benefits.

Quick overview

SeniorityMid Senior
Employment typeFull Time
Work modeRemote
LocationMilwaukee, WI, United States
CRMOutside SalesProspectingSalesforce

Job description

Remote | Wisconsin or Chicago Metro | Base Salary + Commission

Are you an experienced trailer sales professional who enjoys finding new business, building customer relationships, and closing deals? We're looking for a motivated Trailer Sales Executive to grow an established sales territory while working remotely.

You'll sell commercial semi-trailers to trucking companies, fleet operators, and transportation businesses. This opportunity is ideal for someone who understands trailer equipment, knows how to develop new accounts, and enjoys the independence of managing their own sales pipeline.

Trailer Sales Executive Benefits and Compensation:

  • Base salary plus commission
  • Performance-based commission structure with additional earning opportunities
  • Commission opportunities on trailer rental and leasing
  • Medical insurance with PPO and HSA options
  • 401(k) with up to 4% company match
  • Employee wellness programs
  • Remote work with an established sales and operations team
  • Factory and industry trade show opportunities
  • Opportunity to grow an assigned sales territory

Trailer Sales Executive Requirements & Qualifications:

  • 2+ years of successful outside sales experience
  • Direct experience selling commercial semi-trailers, including dry van and/or refrigerated (reefer) trailers
  • Proven success prospecting, developing new accounts, and closing equipment sales
  • Experience selling to trucking companies, fleet operators, or transportation businesses
  • Knowledge of commercial trailer specifications, pricing, and customer equipment requirements
  • Strong communication, negotiation, and customer relationship skills
  • Ability to manage sales activity independently in a remote environment

Must Haves:

  • Direct sales experience with dry van and/or refrigerated (reefer) semi-trailers
  • Proven ability to generate new business rather than relying exclusively on existing accounts
  • Experience identifying customer equipment needs and recommending appropriate trailer solutions
  • Ability to prepare quotes, negotiate pricing, and coordinate equipment orders through delivery
  • Current residence in Wisconsin or the Chicago metropolitan area

Trailer Sales Executive Preferred Background & Skills:

  • Sales experience with both dry van and refrigerated (reefer) trailers
  • Experience selling new and used semi-trailers
  • Trailer rental and leasing experience
  • Established relationships with commercial fleets, trucking companies, or transportation customers
  • Class 8 truck or related commercial equipment sales experience
  • Familiarity with dealership operations, financing, and title documentation
  • Salesforce or comparable CRM experience
  • Experience using digital platforms to prospect and develop new business

This is a remote position. Candidates must currently reside in Wisconsin or the Chicago metropolitan area. Relocation assistance is not provided.

This is a direct-hire position. Third-party staffing, subcontracting, and Corp-to-Corp (C2C) arrangements will not be considered.

Applicants must be legally authorized to work in the United States. The employer will not provide employment visa sponsorship now or in the future.

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