Real Estate Field Agent - Chicago

Mainstay Labs Inc.

1d • $50,000 - $113,000 • Remote

About The Position

Mainstay is seeking a seasoned, Chicago-based Real Estate Agent to manage both acquisitions and dispositions for institutional buyers and sellers of single-family homes. This high-volume, fast-paced role involves putting together and presenting offers, negotiating deals, managing listings from activation to close, and working with a transaction coordinator, pricing team, and field team. The role emphasizes the agent's judgment, negotiation skills, and ability to manage chaos and change in a startup environment, augmented by AI tools. This is a fully remote position within the United States.

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 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.
• 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.

Nice To Haves

• SFR or institutional experience is a major plus.
• Thrive on volume — comfortable with a lot of balls in the air, across markets, with shifting priorities.
• Obsess over the details — know that one missed detail erodes customer trust.
• Negotiate ruthlessly — play to win, don't give up, and keep the customer's terms at the center of every conversation.
• Find calm in chaos, and adopt and champion change — navigate ambiguity without losing your cool or your output, and be the first to test a new tool or workflow.
• Have built your workflow with AI, not just used it — 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.
• Can point to specific gains — more deals closed, faster turnaround, fewer dropped balls — and know when to turn AI off and pick up the phone.

Responsibilities

• Manage both sides of real estate transactions: acquisitions and dispositions.
• Quickly put together and present offers on the acquisition side.
• Negotiate ruthlessly on behalf of customers for acquisitions.
• Manage listings end-to-end on the disposition side, including getting them active, fielding and negotiating offers, and managing deals from contract to close.
• Work with a transaction coordinator for back-of-house tasks.
• Collaborate with pricing and field teams to set strategy and visit homes.
• Know customer playbooks thoroughly.
• Make judgment calls, have hard conversations, and handle small decisions to keep deals together.
• Utilize and integrate AI tools into workflows for offer drafting, CMA analysis, inspection-report summarization, listing copy, and client communication.
• Show up when deals require it, including nights and weekends.

Benefits

• Equity in Mainstay
• Base salary starts at $50,000 with on-target earnings of $113,000+
• Performance-based variable tied directly to the volume and quality of transactions you close.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed