Fleet Parking Specialist

The Opportunity: This is a quota-carrying individual contributor role on our fleet parking team. You'll engage directly with carriers, fleet operators, and large trucking companies to understand their parking needs and match them with the best solutions in our network. Reporting to the VP of Fleet Parking, you'll run the outbound motion — prospecting, discovery, proposals, negotiation, and close. This is a hunting role. You'll work an established playbook rather than build one from scratch, with direct coaching from a senior leader who carries a quota alongside you.

What You'll Do: Sales & Prospecting Meet or exceed monthly and quarterly sales targets Conduct outbound outreach through calls, emails, Linked In, and meetings Research and identify potential fleet customers who operate multiple trucks, trailers, or other assets requiring consistent parking Leverage industry contacts, events, and tools to generate qualified leads Client Engagement & Deal Closing Build strong, long-term relationships with fleet decision-makers Understand client needs regarding locations, asset counts, amenities, and budget Conduct discovery calls and needs assessments Prepare and deliver customized proposals tailored to each fleet's operational challenges Negotiate terms and close new business Customer Support & Supply Coordination Help source new property member locations in markets where customers need parking but supply is limited Provide timely communication and support throughout onboarding Serve as the primary point of contact for your assigned clients Tracking & Reporting Maintain detailed records of outreach, meetings, proposals, and deals in Hub Spot Track KPIs such as conversion rate, pipeline health, and retention Stay current on market trends, competitor offerings, and fleet industry insights

Required Experience & Qualifications: At least 2 years of B2B sales experience; transportation, logistics, or fleet-related industries strongly preferred Experience in trucking or logistics is required Proven track record of meeting or exceeding sales quotas Strong communication, negotiation, and closing skills Highly organized, with solid CRM experience (Hub Spot a plus)Ability to deliver clear presentations and articulate value propositions effectively Ideal CharacteristicsA hunter who thrives on relationship-driven sales and doesn't wait for inbound leads Coachable and competitive — you want a manager who works deals alongside you Credible with fleet operators and dispatchers, and can speak their language Motivated, adaptable, and comfortable in a fast-paced startup environment Thinks in terms of multi-asset commitments and repeat volume, not one-off reservations Why This Role, Why Now Truck Parking Club is at an inflection point. We've proven the model across thousands of locations, and fleets are among the most concentrated, highest-leverage sources of consistent demand. The fleet parking program is being built out now under dedicated senior leadership — specialists who join early get first access to an open market, a defined playbook, and uncapped upside.

What We Offer: Competitive base salary plus commission Comprehensive benefits, including Medical, Dental, and Vision coverage Paid Company Holidays, Paid Sick Leave, and Paid Time Off Meaningful career growth within a rapidly expanding companyA dynamic, collaborative environment focused on innovation and problem-solving