Account Executive (Chicago, IL)

AirGarage • Chicago, IL

1d • $215,000 - $215,000 • Hybrid

About The Position

AirGarage is seeking an experienced Account Executive to own new business in a priority market. This is a hybrid, in-market sales role focused on developing AirGarage’s presence by building relationships with property owners, managers, brokers, and other local partners; spending time at properties and industry events; and turning market insights into opportunities. The Account Executive will sell AirGarage’s parking operations platform, engaging in financial real estate discussions and explaining technical product details to nontechnical buyers. The role serves customers with varied buyer journeys, from fast-moving single-stakeholder deals to complex sales involving national commercial real estate firms. Many prospects already have a parking operator, so the Account Executive must understand existing operations, identify opportunities for improvement, and make a persuasive case for change.

The Account Executive works with a City Manager and SDR as part of the local market team, coordinating sales and operations so customers are supported by a team that understands their city and properties. The role is part of an expanding sales organization and reports to one of two AE leaders, with close collaboration with the VP of Sales. AirGarage is remote-first and expects approximately six weeks of work travel per year for company offsites, location launches, and onboarding. The remainder of the year can be worked remotely from the employee’s dedicated market, with regular fieldwork and attendance at local in-person events.

On-target earnings are $215,000, with a 50/50 base and commission split. Commissions are uncapped and paid monthly. Employment is contingent on successfully completing a background check and employment verification after a conditional offer.

Requirements

• At least 4 years of experience in a quota-carrying, full-cycle sales role, with a record of success and exceeding goals.
• A history of promotions at past companies demonstrating a willingness to work hard and learn quickly.
• Ability to learn AirGarage’s product and the commercial real estate industry quickly and connect effectively with target customers.
• Growth mindset and ability to adapt to constant change in an early-stage startup environment.
• Grit and willingness to do what it takes to succeed.
• Hunter mentality and enthusiasm for prospecting, negotiating, and closing deals.
• Excellent verbal and written communication skills.
• Experience and comfort using Excel for basic profit-and-loss analysis and financial comparisons when preparing proposals.
• Experience working in a smaller startup where the sales playbook is not fully defined.
• Based in or willing to relocate to a priority market; able to work in a hybrid role with regular field time.
• Willingness to travel approximately six weeks per year for work and attend in-person events.
• Comfort explaining technical product details to nontechnical buyers and discussing real estate financial considerations.
• Ability to apply a sales methodology and run a consistent sales process.

Nice To Haves

• Knowledge of the commercial real estate or parking market in the assigned city.
• Experience selling in fast-growing, early-stage startups with mid-market and/or enterprise sales cycles of 60–90 or more days.
• A track record of selling to customers outside the technology sector, including experience with real-world businesses and buyers.

Responsibilities

• Build and work a target account list of parking owners, operators, and commercial real estate firms in the assigned market.
• Partner with the City Manager on local outreach, including property visits, industry events, and introductions through existing AirGarage relationships.
• Pursue new business from prospecting through close, including cold calling, scheduling and conducting personalized demonstrations, handling objections, and winning new customers.
• Work with SDRs to supplement outbound sales efforts and increase the size and throughput of the active pipeline.
• Qualify leads by developing expertise in AirGarage’s product, understanding customer pain points, and explaining how the solution can help.
• Develop knowledge of the parking and commercial real estate industries to negotiate pricing and contract terms effectively.
• Maintain accurate, detailed, and up-to-date pipelines and sales activities in Salesforce CRM.
• Partner with Operations through the deal desk process to develop and structure proposals that are likely to win while remaining healthy for the business.
• Work with the sales team to iterate on and improve the sales process.
• Exceed quarterly sales quotas.
• Travel approximately six weeks per year for company offsites, location launches, and onboarding; attend in-person events throughout the year.

Benefits

• Equity in the business.
• Health insurance; AirGarage currently covers 85% of the cost of medical, dental, and vision plans for the primary employee and 50% for dependents.
• 12 weeks of fully paid parental leave for all parents, usable continuously or intermittently during the first 18 months after a child is born, adopted, or fostered.
• Laptop and additional home-office equipment needed for the role.
• Unlimited paid time off, with a minimum requirement of 10 days per year.
• 401(k) retirement savings program.
• Approximately two full-week team offsites per year.
• Optional recurring book club.
• Opportunities to grow as the company scales.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed