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.

About the Role

We're hiring a seasoned, Chicago-based Real Estate Agent who will 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 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 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 where tools, processes, and customer playbooks evolve regularly. If chaos energizes you and you find calm in the grind, you'll thrive here.

Responsibilities

• Draft, present, and negotiate offers for acquisitions on behalf of institutional buyers.
• Manage end-to-end listing processes for dispositions, including activation, offer negotiation, and contract-to-close coordination.
• Navigate shifting priorities across multiple markets and transactions without letting details fall through the cracks.
• Master and execute customer-specific playbooks for both acquisitions and dispositions.
• Leverage AI tools (off-the-shelf and proprietary) to augment workflows in offer drafting, CMA analysis, inspection-report summarization, listing copy, and client communication.
• Exercise judgment to determine when to use AI versus manual processes, ensuring accuracy and Fair Housing compliance.
• Work evenings and weekends as required by transaction timelines.

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 with demonstrated expertise in both acquisitions and dispositions.
• Specific, demonstrable AI workflows built around general-purpose LLMs (e.g., ChatGPT, Claude, Gemini) and/or real-estate-specific AI tools (e.g., Follow Up Boss AI, Compass AI, Real's Leo). Include a 2-minute Loom video in your application walking through one workflow and its impact.
• Strong judgment about when not to use AI, and ability to evaluate AI outputs for accuracy and Fair Housing compliance.
• Proficiency in Salesforce or similar CRM, G-Suite, Slack, MacOS, and multitasking across multiple systems.
• Exceptional written and verbal communication skills to represent Mainstay and our customers confidently.
• Reliable access to a smartphone and computer for task completion, documentation, and communication.
• Comfort working evenings and weekends when transactions require it.

Skills

• Seasoned super-agent with 5+ years of hands-on transaction experience, ideally across both buy and sell sides.
• Thrive in high-volume environments with shifting priorities and multiple markets.
• Obsess over details to maintain customer trust and keep deals together.
• Ruthless negotiator who plays to win while keeping customer terms central.
• Adapt quickly to evolving tools and processes in a fast-moving startup.
• Built AI workflows (e.g., custom GPTs, automations) that drive measurable gains in deals closed, turnaround time, or pipeline management.

Benefits

• Shape the future of the single-family rental industry as part of the leading market intelligence platform.
• Own the entire transaction journey from offer-to-contract and contract-to-close with real authority.
• Dedicated teams for pricing, field visits, and transaction coordination, plus an AI-augmented stack to handle back-of-house workflows.
• Bring and expand your AI workflows in an AI-native company built on Claude, with a team shipping new tools weekly.
• Equity in a fast-growing Series A company backed by Khosla Ventures and founded within Opendoor.

Pay

Base salary starts at $50,000 with on-target earnings of $113,000+, structured as base pay plus performance-based variable compensation tied directly to the volume and quality of transactions closed. Our AI-augmented operations stack handles 30–40% of traditional agent workload, allowing you to focus on high-impact activities like negotiation and deal management.