The posting, in Mainstay Labs Inc.'s own words
archived Sep 8, 2026About 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.
Read the full posting ↓
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.