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.
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Active Illinois real estate license, and residence in the Chicago metro
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Willingness to obtain licenses in additional Mainstay markets after hire (see Compensation)
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5+ years of experience as a licensed real estate agent
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Demonstrated listing experience — pricing and launching listings, fielding and negotiating offers, and contract-to-close coordination
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A reliable vehicle, a valid driver’s license, and willingness to drive across the metro daily. Mileage is reimbursed
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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
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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
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Strong written and verbal communication; able to represent Mainstay and our customers confidently to agents and counterparties
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Comfort working evenings and weekends when transactions require it