Account Executive, Parking and Reservations

Role Overview

• 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.

Requirements

• 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.
• Understanding of truck parking, yards, terminals, or industrial real estate, preferred.
• CRM power user with strong pipeline discipline, preferred.

Benefits

• Health Insurance: FREE medical coverage for employees for one of our plan options! And the ability to add dependents or choose an alternative plan and still receive a credit to keep costs down.
• Paid Time Off: Work hard, play hard! In addition to 10 holidays, we offer three weeks of paid time off so that you can achieve a healthy work-life balance.
• Paternity Leave: We support our team members as they grow their families! Once you qualify for FMLA, you are eligible to receive up to 6 weeks of paid paternity time to bond with a new child.
• Employee Assistance Program: We are proud to offer free access to SupportLinc, a global platform that provides on-demand care as you navigate personal or professional challenges. This confidential and compassionate support system is available to you and your family members anytime you need help.
• Team Building: We may work across time zones and countries, but we’re still united. We host a monthly schedule of team activities, quarterly town halls, open Q&A sessions, and other special events…so many fun ways for us to connect and support one another.
• Growth Opportunities: When our people grow…we grow! We offer leadership training, development journeys for core teams, and coaching/mentoring opportunities. Constant growth and development are inherent in our culture.
• Tools To Do The Job: We ensure you are hooked up with the tools, equipment, and systems you need. We begin the process prior to your start date, so you are ready to rock ‘n roll on your first day.
• 401(k) company match and 100% company-paid life/AD&D insurance/short-term disability.