Real Estate Field Agent - Chicago

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 who eats, breathes, and lives this business. You'll own both sides of the transaction - acquisitions and dispositions - for some of the largest institutional buyers and sellers of single family homes in the country.

On the acquisition side, you'll work quickly to put together and present offers, then negotiate ruthlessly on behalf of our customers. On the disposition side, 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 a pricing and field team to help you set strategy and visit homes.

This is a high-volume role at a fast-moving Series A startup. Tools change. Processes change. Customers each have specific playbooks you'll be expected to know cold. If chaos energizes you and you find calm in the grind, you'll thrive here.

This is the kind of work AI doesn't do well — judgment calls, hard conversations, and the dozen small decisions that keep a deal together. That's why we hire seasoned agents and pair them with the best AI tools we can find — off-the-shelf and proprietary — to multiply what one great agent can do.

This role is fully remote within the United States.

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.
• Thrive on volume — You're comfortable with a lot of balls in the air, across markets, with shifting priorities. Nothing falls through the cracks.
• 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.
• Find calm in chaos, and adopt and champion change — Tooling and process evolve regularly at a Series A startup. You navigate ambiguity without losing your cool or your output, and you're the first to test a new tool or workflow rather than the last.
• Have built your workflow with AI, not just used it — You don't just use ChatGPT to draft emails. You've built workflows, custom GPTs, or automations that help you manage a real pipeline and are genuinely excited to help us launch new tools across offer drafting, CMA analysis, inspection-report summarization, listing copy, and client communication. You can point to specific gains — more deals closed, faster turnaround, fewer dropped balls — and you know when to turn AI off and pick up the phone. You'll be expected to walk us through specific examples.
• Show up when deals need you — Real estate doesn't sleep. Nights and weekends come with the territory.

REQUIREMENTS

• Active real estate license in Illinois plus licenses in at least 2 other states within our operating footprint (GA, FL, TX, NC, AZ, TN, AL, IN, OH, MO, KS, NV, CO, CA, OK), with willingness to obtain additional licenses post-hire
• 5+ years of experience as a licensed real estate agent
• Demonstrated experience managing both acquisitions and dispositions — drafting and presenting offers, negotiating terms, listing management, and contract-to-close coordination
• Specific, demonstrable AI workflows — built your workflows around using at least one general-purpose LLM (ChatGPT, Claude, or Gemini) and ideally one real-estate-specific AI tool (Follow Up Boss AI, Compass AI, Real's Leo, or equivalent) — that you've used to manage a real pipeline. As part of your application, please include a 2-minute Loom walking us through one workflow you've built and the impact it's had.
• 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, and the ability to work in multiple systems simultaneously
• Strong written and verbal communication skills; able to confidently represent Mainstay and our customers to agents, buyers, and sellers on the other side of the table
• Reliable access to a smartphone and computer for task completion, documentation, and communication
• Comfort working evenings and weekends when transactions require it

COMPENSATION

Base salary starts at $50,000 with on-target earnings of $113,000+, structured as base pay plus performance-based variable tied directly to the volume and quality of transactions you close. As a Series A company, we also offer equity in Mainstay so you share in the upside as we grow.

We can offer a base on top of commission because our AI-augmented operations stack — pricing, field visits, transaction coordination, and the back-of-house workflows that typically eat 30–40% of an agent's week — is handled by dedicated teams and tooling. You spend your time where AI can't: judgment calls, negotiation, and keeping deals together.

WHY JOIN MAINSTAY

• 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 both the offer-to-contract and contract-to-close journey, with real authority to make the calls that keep deals together.
• A team and tools that back you — Dedicated pricing, field visits, and transaction coordination teams, plus an AI-augmented stack that handles HOA/tax workflows and back-of-house ops, keep you focused on what you do best: offers, negotiations, and closings.
• 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.
• Series A momentum — Backed by Khosla Ventures, founded inside Opendoor, growing fast.

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.

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