Fleet Parking Specialist

Fleet Parking Specialist Truck Parking Club Remote (U.S.) Full-Time Compensation: Base + Commission

About Truck Parking Club

Truck Parking Club is the leading marketplace connecting commercial truck drivers and fleets with instantly reservable hourly, daily, weekly, and monthly parking at properties across the United States. Through truckparkingclub.com and our mobile app, we unlock secure, convenient parking for drivers while generating new ancillary revenue for our property members.

Our network includes trucking companies, truck repair shops, tow operators, storage facilities, CDL schools, trailer leasing companies, real estate investors, truck stops, and parking operators. Our fleet and carrier program is one of our highest-leverage demand channels, and we're scaling a dedicated team to make Truck Parking Club the default parking partner for fleets nationwide.

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, LinkedIn, 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 HubSpot
• Track KPIs such as conversion rate, pipeline health, and retention
• Stay current on market trends, competitor offerings, and fleet industry insights

Who You Are

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 (HubSpot a plus)
• Ability to deliver clear presentations and articulate value propositions effectively

Ideal Characteristics

• A 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 company
• A dynamic, collaborative environment focused on innovation and problem-solving

Pay: $65,000.00 - $135,000.00 per year

Benefits:

• Dental insurance
• Employee discount
• Flexible spending account
• Health insurance
• Health savings account
• Life insurance
• Paid time off
• Parental leave
• Vision insurance

Work Location: Remote