Business Development & Fleet Sales Representative

Trailer Boss

Location: Olympia, WA (Preferred Home Base)

About Trailer Boss

Trailer Boss is a leading trailer dealership in the Pacific Northwest, serving both retail and commercial customers. With continued growth across multiple markets, we are expanding our commercial and fleet sales capabilities. To support this, we are seeking a professional, driven Business Development & Fleet Sales Representative to help build new business relationships and strengthen our presence in regional commercial sectors.

This role focuses on generating new commercial business, managing fleet relationships, and executing consistent outbound outreach across a defined territory. The ideal candidate will be comfortable meeting with customers in person, presenting product solutions on-site, and engaging directly with businesses, contractors, agricultural operations, industrial clients, and municipal organizations.

This is a hybrid field and office role, with regular travel to customer locations and job sites.

• Develop and manage a commercial sales territory, focusing on fleet, contractor, industrial, agricultural, and municipal clients.
• Conduct outbound prospecting, including site visits, scheduled meetings, product presentations, and industry introductions.
• Represent Trailer Boss professionally at trade shows, events, and relevant industry gatherings.
• Build long-term relationships with business owners, purchasing managers, and operational leaders.
• Prepare and deliver proposals, quotes, and commercial pricing packages.
• Maintain a structured sales pipeline using CRM tools and follow consistent sales processes.
• Identify customer needs and provide trailer solutions that meet operational and commercial requirements.
• Travel throughout the Pacific Northwest, with 2–3 days per week spent in the field.

• 3 years of B2B sales experience, ideally within equipment, automotive, construction, trucking, agriculture, or industrial product sectors.
• Strong interpersonal, presentation, and communication skills.
• Ability to work independently, manage a territory, and maintain consistent outreach.
• Comfortable visiting businesses, job sites, farms, industrial facilities, and commercial operations.
• Valid driver’s license with a clean driving record.
• Strong organizational skills and experience with CRM systems.
• Professional, self-motivated, and accountable.

• Base salary plus commission (experience dependent)
• Medical benefits available
• PTO and paid holidays
• Professional onboarding, training, and sales support
• Opportunities for long-term growth and advancement within a growing organization

This position plays a key role in expanding our commercial and fleet sales footprint. You will have the autonomy to build a territory, the flexibility to engage businesses in person, and the opportunity to help shape a growing revenue channel. We’re looking for a professional who values building relationships, creating new opportunities, and representing high-quality products with integrity.

If you’re driven by results and enjoy connecting directly with businesses, we invite you to apply.