This one’s a pure hunter role. New logos, enterprise fleets (150+ vehicles), quota-carrying, heavy pipeline building, and you’re expected to eat what you kill. Big upside if you can sell. Big pain if you can’t.
About Fleetworthy
Fleetworthy is a fleet safety, compliance, and toll management platform (Bestpass, Drivewyze, ExpressTruckTax rebranded under one roof). They sell software + services that help fleets reduce risk, run safer, and stay compliant while cutting operational friction.
Schedule
- Remote or local (territory-based)
- Travel as needed
- Base + commission: $130,000–$150,000 base + commissions
- 12-month territory plan focus: build pipeline, close deals, beat quota
What You’ll Do
⦁ Own a region/territory and close against a quota
⦁ Build and execute a territory plan to sell into enterprise fleets (150+ vehicles/drivers)
⦁ Prospect, secure appointments, and develop relationships with decision-makers (C and VP levels)
⦁ Run complex sales cycles: discovery → value framing → business case → close
⦁ Position Fleetworthy’s suite (compliance, safety, toll management, bypass, etc.) to fleet pain points
⦁ Forecast monthly/quarterly pipeline and keep Salesforce clean and accurate
⦁ Partner internally with Account Management, Customer Success, Ops, Support to ensure customer satisfaction post-close
What You Need
⦁ Bachelor’s degree required
⦁ 5+ years of face-to-face solution selling experience
⦁ Strong consultative selling ability (reframe the customer’s thinking, sell outcomes first)
⦁ Enterprise sales chops: multi-stakeholder, cross-org selling at senior levels
⦁ Experience building territory plans and running a structured sales process
⦁ SaaS selling preferred
⦁ Selling into large fleet businesses preferred
⦁ Strong presentation and communication skills
Benefits
Not listed in your paste, but the comp range is the headline here: high base, commission on top, likely performance-driven culture.
Straight talk: this is not “remote chill.” This is “pipeline, meetings, rejection, repeat.” If you don’t have a real hunter track record (new business, quota, enterprise cycles), it’ll chew you up. If you do, the base is serious and the commission can get spicy.
Happy Hunting,
~Two Chicks…