Account Executive (Chicago, IL) [Remote]

About AirGarage

AirGarage is on a mission to bring real estate online, starting with parking.

We replace broken parking machines, fragmented software, and manual, labor-intensive operations with a unified, data-rich operating system for parking real estate. We handle everything it takes to run and optimize a parking asset: payments, dynamic pricing, enforcement, license plate recognition, analytics, and more.

By building all of our technology in-house, we are able to deliver a magical experience for drivers while providing real-time visibility and revenue increases of 20-50% or more for real estate owners. That’s why national real‑estate leaders like Hines and Greystar, as well as technology companies like Meta, partner with AirGarage to optimize their parking facilities.

AirGarage uses datapoints like real-time occupancy, local events, weather, driver behavior, competitor pricing, and more to bring true intelligence to real estate owners’ assets for the first time.

We’re investing aggressively to make the physical world legible to a digital system: cameras, sensors, and software that generate a firehose of real-time data about the world around us. That data fuels models and algorithms that allow us to optimize performance at each property while giving owners the clarity and control they’ve never had before.

Before you can optimize an asset, you need to observe it. Before you can observe it, you need to bring it online.

We are starting with the $131 billion US parking real estate market because it is one of the most offline and mismanaged commercial real estate asset types. 26% of the land area in the median American urban core is dedicated to parking.

We are backed by top tier investors including Headline Growth, Andreessen Horowitz, Floodgate, Founders Fund, Abstract Ventures, and angel investors who have founded or worked at companies like Uber, Opendoor, Flexport, and more.

THE ROLE

Note : This role requires being based in Chicago, Illinois. We’re also hiring Account Executives in Los Angeles , Denver , Boston , and Ohio (Cleveland, Cincinnati, or Columbus) . Based somewhere else? We’re still open to strong talent anywhere in the US, so please apply through our general posting .

We are seeking an experienced Account Executive to own new business in one of AirGarage's priority markets. This is an in-market role: Build AirGarage’s presence in your market by developing relationships with property owners, managers, brokers and other local partners. Spend time at properties and industry events, and turn what you learn into new opportunities.

You'll need to be a fast learner with strong sales and interpersonal skills, capable of engaging in dollars-and-cents real estate conversations in addition to having the ability to go deep in the weeds effectively communicating the finer details of a technical product to a non-technical buyer.

You'll develop an understanding of the buyer journey for many different customer types including fast moving, single stakeholder deals as well as complex multi-party sales with national commercial real estate firms.

Build AirGarage’s presence in your market by developing relationships with property owners, managers, brokers and other local partners. Spend time at properties and industry events, and turn what you learn into new opportunities.

Many of your prospects already have a parking operator in place. You’ll need to understand their current operation, identify opportunities to improve it, and make a compelling case for change to owners and other stakeholders.

Together, the AE, City Manager, and SDR form AirGarage's local team in each market, combining sales and operations so customers work with one team that knows their city and their properties.

The ideal candidate for this role is someone with a proven track record of success selling into “the real America” (i.e. you weren’t just selling SaaS to other technology companies), who has been promoted consistently while growing and developing themselves personally.

You will be joining an existing team of 10 Account Executives, and 14 SDRs reporting into one of our two AE leaders, and collaborating heavily with our VP of Sales. We are growing quickly and investing heavily in scaling out the sales team to support that growth.

SALES COMPENSATION

• On-Target Earnings of $215k with a 50/50 base and commission split.

• Commissions are uncapped and paid out on a monthly basis.

WHO YOU ARE

• You want to own a market. You'd rather know every major property owner in your city by name than be one more email in their inbox.

• You have a deep need to understand the customer and win the deal. You aren’t just in sales to make money, you see sales as a path to helping customers achieve their goals and drive win-win-win outcomes for the customer, yourself, and the business.

• You have a proven track record of selling in fast growing, early stage startups with a mid-market and / or enterprise sales cycle (60-90+ days) and without having a perfect playbook written out for you.

• You are obsessed with understanding the product that you are selling at a deep level such that you can answer edge case questions from a customer confidently and competently while explaining it in terms that they understand.

• You have a strong grasp of and consistently apply a sales methodology such that you run a strong sales process every time and maximize your odds of winning the deal.

WHAT YOU WILL DO

• Build and work a target account list of parking owners, operators, and commercial real estate firms in your market.

• Partner with your City Manager on local outreach, including in-person property visits, local industry events, and introductions through existing AirGarage relationships in the city.

• Exceed your quarterly sales quota by pursuing new deals from start to finish - including prospecting, cold calling, scheduling & conducting highly personalized demos, overcoming objections, and ultimately pulling new customers across the finish line.

• Work closely with SDRs to supplement your own outbound efforts and increase the size and throughput of your active pipeline.

• Qualify leads by becoming an expert on AirGarage, understanding customer pain points, and conveying how AirGarage's solution can help.

• Develop an understanding of the parking and commercial real estate industry to enable you to effectively negotiate pricing & contract terms.

• Become an expert in our Salesforce CRM and make sure pipelines and activities are consistently up to date and accurate to the highest level of attention and detail.

• Partner with Operations through the deal desk process to propose and structure proposals that are most likely to win the deal while being healthy for the business as well.

• Work with the rest of the sales team to iterate and improve on our sales process. We are always looking for ways to improve and you can contribute actively to that process once you have ramped up and are consistently winning with prospects.

WHAT YOU NEED ⭐️

• Based in, or willing to relocate to, one of our priority markets. This is a hybrid role with regular time in the field meeting owners and visiting properties.

• Knowledge of the commercial real estate or parking market in your city is a plus.

• 4+ years in a quota carrying, full cycle sales role with a track record of success and exceeding goals.

• A history of promotions through roles at your past companies that demonstrates your desire to work hard and learn fast.

• Ability to quickly learn about AirGarage, as well as the Commercial Real Estate industry at large, in order to effectively connect with our target customers.

• A growth mindset and ability to adapt quickly in an early stage startup environment where change is constant.

• Grit and the willingness to do whatever it takes to succeed.

• Hunter mentality - you are excited about prospecting, negotiating, and live to close deals.

• Excellent verbal and written communication skills.

• Experience and comfort working in excel to complete simple profit & loss analysis and financial comparisons when preparing proposals.

• Experience working in a smaller startup environment where the playbook is not well defined in its entirety for you.

IMPORTANT NOTE

AirGarage is a remote-first company, but we also value in-person collaboration to strengthen trust and teamwork. Team members should expect ~6 weeks of travel per year for:

• 2–3 full company offsites, “Remote Weeks”

• Lending a hand to support at least one new location launch

• In-person onboarding as well as supporting other onboarding sessions for new team members

The rest of the year, team members can work remotely from their dedicated market. Attendance at in-person events throughout the year is expected—if you’re not open to traveling ~6 weeks per year for work, our team won't be a good fit for you.

THE UPSIDE

• Equity: Have a stake in the business that you’re helping to build and grow.

• Health insurance: We offer health insurance and currently cover 85% of the cost of medical, dental, and vision plans for the primary employee and 50% of the cost of plans for dependents.

• Parental Leave: We offer 12 weeks of fully paid parental leave to all parents to bond with a newly born, adopted, or fostered child. The 12 weeks can be taken as a continuous leave or intermittently over the first 18 months of the child's life.

• Home office setup: Get a laptop + additional equipment needed to set you up for success.

• ⛺ Time to recharge: We have an unlimited PTO policy with a minimum requirement of 10 days per year.

• 401k: Make financial planning right for you with a 401k retirement savings program.

• ✈️ Team Off-sites: ~2 times per year our team comes together for a full week in places like Tahoe, Charleston, San Diego, Park City, and Austin.

• BookGarage: Our team loves to learn and grow together, so join us for our optional recurring book club.

• Room to grow: Our team will be orders of magnitude larger within a few years; as a part of our foundational team, you'll have opportunities to grow with us.

• ️ Transform our cities: The opportunity to change the way that the world thinks about real estate use in our cities.

• Work with a diverse team: At AirGarage, we've always been committed to building a thriving team that represents the communities we serve. Our team is currently 40% female and 30%+ from underrepresented communities.

Note : Employment with AirGarage is contingent upon successful completion of a background check and employment verification conducted in compliance with applicable laws. Background checks are completed only after a conditional offer of employment has been made.

We understand that there's no such thing as a 'perfect' candidate. We're looking for someone passionate, with grit and determination, who is excited to face the challenges of a rapidly growing startup. AirGarage is the type of company where you can grow exponentially, and we encourage you to apply to us even if you don't 100% match the candidate description.

AirGarage is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. Candidates and employees are always evaluated based on merit, qualifications, and performance. We will never discriminate on the basis of race, color, gender, national origin, ethnicity, veteran status, disability status, age, sexual orientation, gender identity, marital status, mental or physical disability, or any other legally protected status.