If you’re a true hunter who lives for pipeline builds and closed-won alerts, this role is built for you. You’ll own a region, sell into large enterprise fleets, and drive revenue growth with a product suite that solves real safety, compliance, and cost problems.
About Fleetworthy
Fleetworthy provides a complete fleet readiness technology suite that unites safety and compliance, toll management, and weigh station bypass. Trusted by 75% of the top fleets in North America, they support millions of vehicles and drivers and are recognized for innovation and industry leadership. Their AI-enabled connected fleet tech helps fleets stay safe, compliant, and running efficiently.
Schedule
- Full-time
- Remote or local (based on territory/region needs)
- Travel as necessary
- Compensation: $130,000 to $150,000 base salary plus commissions
What You’ll Do
- Own an assigned territory and close deals against quota
- Build and execute a 12-month strategic plan to grow business in your region
- Create and drive a strong pipeline selling into enterprise fleets with 150+ vehicles/drivers
- Identify and build relationships with new prospects and key decision-makers
- Position Fleetworthy’s software, products, and services to match customer pain points and operational needs
- Help customers build business case justification for purchasing Fleetworthy solutions
- Maintain accurate Salesforce records, including activity, pipeline, and results
- Forecast sales activities and pipeline monthly and quarterly
- Partner with Account Management, Customer Success, Operations, and Support to ensure strong customer satisfaction
- Continuously develop and nurture relationships with C-level, VP-level, and other key stakeholders
What You Need
- Bachelor’s degree (required)
- 5+ years of face-to-face solution selling experience
- Ability to reframe customer thinking and structure pitches around customer benefits first
- Strong two-way communication skills and the ability to connect value props to real pain points
- Proven ability to build and execute opportunity and territory plans
- Comfort selling cross-organizationally, including C and VP levels
- Ability to articulate sales stages and navigate complex account sales processes
- Strong prospecting skills: identify targets, secure appointments, and run a strategic sales process
- Excellent written, verbal, and presentation skills
- SaaS selling experience (preferred)
- Experience selling to large fleet businesses (preferred)
Benefits
- Base salary range of $130,000 to $150,000 plus commissions
- Remote or local flexibility (role dependent)
- Growth-focused team environment in a market-leading fleet tech company
This is quota-driven and growth-critical, so if you’re built to hunt and you want a role that rewards it, move now.
If you can build trust fast, sell value up the chain, and consistently close enterprise deals, this is a strong lane.
Happy Hunting,
~Two Chicks…