Commercial Fleet Sales Representative

Chicagoland Territory

Outside B2B Sales | Chicagoland | Uncapped Earnings

Do you thrive on winning new business? Are you the type of salesperson who enjoys opening doors, building relationships, and closing deals? The Chicagoland Jiffy Lube Co-op is looking for an ambitious, self-motivated Commercial Fleet Sales Representative to grow our fleet business across the Chicago metropolitan area.

This is an opportunity to build your own book of business while representing one of the most recognized automotive service brands in the country.

What You'll Do

• Prospect and develop new commercial fleet accounts throughout Chicagoland
• Build relationships with local businesses, municipalities, contractors, delivery companies, and other fleet operators
• Schedule and conduct face-to-face sales meetings
• Generate your own pipeline through networking, referrals, cold calling, and community outreach
• Manage opportunities from first contact through signed agreement
• Become a trusted advisor for customers' preventive maintenance needs

What Makes You Successful

• You enjoy prospecting and generating your own opportunities
• You are comfortable meeting with owners, operations leaders, and fleet managers
• You are highly organized and accountable
• You can work independently with minimal supervision
• You are motivated by commissions and performance-based rewards
• You understand how to build long-term business relationships

Qualifications

• 3+ years of business-to-business sales experience
• Proven track record of generating new business and exceeding sales goals
• Experience managing a sales pipeline and closing opportunities
• Strong presentation, negotiation, and relationship-building skills
• Familiarity with CRM systems such as Salesforce, HubSpot, or similar platforms
• Valid driver's license and reliable transportation

Preferred

• Fleet services experience
• Automotive services experience (Not required)
• Commercial transportation experience
• Experience selling into municipalities, contractors, or multi-location businesses
• Established Chicagoland business network

Compensation

• Base compensation, plus uncapped commision
• First-year earning potential $70,000 - $120,000
• Mileage reimbursement
• Monthly health insurance stipend
• Flexible schedule
• Significant earning potential for high performers

This is a 1099 independent contractor engagement offering significant autonomy and flexibility. The selected professional will operate independently while partnering closely with the Chicagoland Jiffy Lube Co-op to grow commercial fleet business across participating locations.

Territory

This role supports the greater Chicagoland market and requires in-person business development activities throughout the region.

Why Join Us?

This is a unique opportunity to build commercial relationships on behalf of a trusted national automotive brand while helping local businesses keep their fleets operating efficiently. You'll have the freedom to develop your own territory strategy, leverage your professional network, and directly influence your earning potential.

Work schedule

• Other

Supplemental pay

• Commission pay

Benefits

• Flexible schedule
• Mileage reimbursement