Real Estate Agent - Chicago Metro

About Mainstay

Mainstay is the leading market intelligence platform purpose built for buying, managing, and selling homes in the single family rental industry. As an AI native company, we turn complex data into clarity that helps the industry move forward with confidence. Founded within Opendoor, Mainstay launched as an independent company in 2024 and recently raised a Series A round led by Khosla Ventures.

Ready to shape the future of real estate with AI? Join Mainstay and help us redefine what’s possible in the single family rental space. If you thrive on solving complex problems and want to make a tangible impact in a fast-growing industry, we’d love to hear from you - apply now and let’s move the industry forward, together!

About the Role

We're hiring a seasoned, Chicago-based Real Estate Agent to stand up our presence in a brand-new market. You'll own the disposition side end to end for some of the largest institutional owners of single family homes in the country. You will be the first aMainstay agent on the ground in Chicago, and how this market goes is largely down to how you run it.

This is not a remote desk job. Chicago cannot be served from a laptop. Illinois is an attorney-review state. Many municipalities require a point-of-sale inspection that you will attend in person. Listings have to go live within 48 hours or the customer is fined. You will be in the field regularly — pre-walking homes before they list, attending inspections, and often laying eyes on a property yourself. You'll manage listings end-to-end: getting them active, fielding and negotiating offers, and keeping deals together from contract to close.

You'll have a transaction coordinator handling the back-of-house work once under contract, plus pricing and field teams to help you set strategy. Pre-walks and inspection attendance are yours — that is the part of this job that cannot be delegated, and it is why the role is compensated differently from our remote agent roles.

This is a high-volume role at a fast-moving Series A startup.

Location and territory

You'll be based in the Chicago metro. The centre of gravity for our current book is the south and southwest suburbs — roughly the Oak Lawn, Palos Heights, Orland Park corridor — and living in or near that arc will make your week materially easier.

We want to be straight with you about the territory, because it will change. Today the work concentrates in the south suburbs. As volume grows it will spread across the metro, including the southwest corridor toward Plainfield, Joliet, and Aurora, and into the city. This is a metro-wide field role, not a south-suburban territory. Expect real windshield time, and expect that to be a permanent feature of the job rather than a start-up phase.

Who You Are

This role is built for real estate professionals who:

Are seasoned super-agents — 5+ years of active, hands-on transaction experience, ideally across both buy and sell side. SFR or institutional experience is a major plus.

Know Chicago — You understand the south suburbs, the municipal transfer stamp and point-of-sale inspection regimes, and how attorney review actually plays out. You don't need a map to get to Matteson.

Are genuinely willing to be in the field — This is the difference between thriving here and burning out. You are comfortable spending a large share of your week in the car and at properties, in Chicago weather, year-round.

Thrive on volume and change — You're comfortable with a lot of balls in the air and shifting priorities, and nothing falls through the cracks. Tooling and process evolve regularly at a Series A startup, and you're the first to test a new workflow rather than the last.

Obsess over the details — You know that one missed detail erodes customer trust. You sweat the small stuff because the small stuff is what keeps deals together. Our customers each have specific playbooks, and you take pride in knowing them cold.

Negotiate ruthlessly — You play to win, you don't give up, and you keep the customer's terms at the center of every conversation.

Have built your workflow with AI, not just used it — You've built workflows, custom GPTs, or automations that manage a real pipeline, and you can point to specific gains: more deals closed, faster turnaround, fewer dropped balls. You also know when to turn AI off and pick up the phone.

Requirements

• Active Illinois real estate license, and residence in the Chicago metro

• Willingness to obtain licenses in additional Mainstay markets after hire (see Compensation)

• 5+ years of experience as a licensed real estate agent

• Demonstrated listing experience — pricing and launching listings, fielding and negotiating offers, and contract-to-close coordination

• A reliable vehicle, a valid driver's license, and willingness to drive across the metro daily. Mileage is reimbursed

• Judgment about when not to use AI, and the ability to evaluate AI outputs for accuracy and Fair Housing compliance before they reach a client or counterparty

• Strong technical skills: Salesforce or a similar CRM, G-Suite, Slack, MacOS, the ability to work in multiple systems at once, and reliable access to a smartphone and computer

• Strong written and verbal communication; able to represent Mainstay and our customers confidently to agents and counterparties

• Comfort working evenings and weekends when transactions require it

Compensation

Base salary of $50,000, rising to $55,000 once you hold six state licenses.

Variable pay is $750 per Chicago close — well above our standard agent rate, because this role carries field obligations most agent roles don't. Closes in other Mainstay markets pay our standard tiered rate. On-target earnings are $106,000 to $125,000 depending on transaction volume.

You can also earn up to $15,000 in license milestone bonuses — $5,000 for each of your first three licenses beyond Illinois, paid quarterly over the year following each license going active. We pay all license fees, MLS dues, and mileage.

As a Series A company, we also offer equity in Mainstay so you share in the upside as we grow.

Why Join Mainstay

Own a market — You are not joining a Chicago team. You are the Chicago team, building it from the first listing. What we do here next depends on how this goes.

Shape the category — We're the leading market intelligence platform in single family rental, and you'll work directly with the largest players in the industry.

Real ownership — This isn't transaction coordination. You own the listing from launch through closing, with real authority to make the calls that keep deals together.

Bring your AI workflows — We're AI-native by design and built on top of Claude. Bring what you've built; you'll learn from a team shipping new workflows every week.

Mainstay Built on Trust

At Mainstay, trust is at the core of everything we do. We build trust with everyone -- from candidates to employees to partners. We believe in fairness and openness throughout our hiring process, evaluating candidates based on qualifications without regard to race, color, religion, national origin, age, gender, marital status, disability, veteran status, sexual orientation, gender identity, or any other protected status. Our privacy practices describe how we handle applicant information, you can find the policy details for California residents here.

We are committed to providing reasonable accommodations throughout our recruitment processes for candidates with disabilities, pregnancy, religious beliefs, or other reasons protected by applicable laws. If you require assistance or a reasonable accommodation, please contact us at mainstay-recruiting@opendoor.com