Account Executive, Parking and Reservations

We are on the lookout for an Account Executive, Parking and Reservations to join our growing team!

Trucker Path is a high-growth global SaaS company revolutionizing transportation technology for the trucking industry. Our flagship app is the most popular navigation and mobility solution for professional truck drivers in North America, with over 1 million active users - nearly one-third of all long-haul drivers. From truck-safe routing and real-time parking availability to fuel pricing, weigh station updates, and more, Trucker Path empowers drivers with the tools they need to operate efficiently and safely.

With a dynamic, collaborative culture that spans multiple countries and time zones, we’re building innovative solutions that keep the transportation industry moving forward. Join us on our exciting journey and help shape the future of transportation technology!

One of our fastest-growing areas is our Parking & Reservations division, which is focused on solving one of the industry’s most urgent challenges: safe, reliable, reservable truck parking. We work directly with fleets, carriers, brokers, and industrial property owners to unlock parking capacity and drive utilization through a growing national reservation network. As this business scales, we’re building the commercial engine that will power its growth.

Trucker Path is hiring a Account Executive, Parking and Reservations to drive revenue for our Parking & Reservations division, based in Chicago. This role sits at the center of revenue growth and is ideal for a high-performing seller who thrives in a hunter + closer environment. You’ll own the full sales cycle, build long-term commercial relationships, and expand utilization across our growing parking supply network.

• Own the full sales cycle from prospecting and discovery through proposal, close, and expansion.
• Sell short-term and long-term reserved parking agreements to:
  Fleets and asset-based carriers; 3PLs and brokers; OEMs, shippers, and enterprise logistics operators
• Close multi-location and multi-month parking contracts.

• Manage and grow a defined regional territory (Chicago metro).
• Develop strategic accounts aligned with major freight corridors, terminals, and hubs.
• Conduct in-person meetings with customers and partners as needed.

• Build and maintain a strong, well-qualified pipeline using CRM with disciplined hygiene.
• Accurately forecast bookings and revenue.
• Partner closely with operations and supply teams to ensure smooth deal execution and customer delivery.

• Act as the voice of the customer to product and leadership teams
• Identify trends in fleet behavior, pricing sensitivity, and parking demand.
• Contribute to go-to-market strategy as the network expands nationally.

The Account Executive, Parking and Reservations role is about selling a real solution to a real industry pain point. With growing parking shortages, increased ELD enforcement, and rising fleet safety requirements, demand for reservable truck parking is accelerating fast. You’ll have direct access to leadership, influence how the division scales, and help shape a business with massive tailwinds and tangible impact.

You’ll be fully remote in the Chiacgo-metro area. Our headquaretrs is based out of our stunning, light-filled space in the Warehouse District of Downtown Phoenix—a 17,000-square-foot space designed for collaboration, creativity, and connection.

This role offers a competitive base salary range starting at $85,000 plus uncapped commissions with opportunities for growth based on performance.

• 3+ years of B2B sales experience (logistics, transportation, SaaS, real estate, or industrial services preferred).
• Proven ability to close recurring-revenue or contract-based deals.
• Comfort selling to operational, safety, and executive stakeholders.
• Strong negotiation, communication, and follow-through skills.
• Willingness to be in the field as needed.
• Experience selling to fleets, carriers, or logistics operators, preferred.
• Unders…