Real Estate Field Agent - Chicago

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. This is a high-volume role at a fast-moving Series A startup. This role is fully remote within the United States.

Responsibilities

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; Work quickly to put together and present offers, then negotiate ruthlessly on behalf of our customers; Manage listings end-to-end on the disposition side: getting them active, fielding and negotiating offers, and keeping deals together from contract to close; Make judgment calls, have hard conversations, and handle the small decisions that keep a deal together; Work as a high-volume agent in a fast-moving Series A startup, adapting to changing tools and processes; Use AI tools to multiply what one great agent can do

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, 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

Nice to have

Buy and sell side experience; SFR or institutional experience; Real-estate-specific AI tool (Follow Up Boss AI, Compass AI, Real's Leo, or equivalent)

Benefits

Equity in Mainstay; Shape the category — work directly with the largest players in the single family rental industry; Real ownership of the offer-to-contract and contract-to-close journey with real authority; Dedicated pricing, field visits, and transaction coordination teams; AI-augmented stack that handles HOA/tax workflows and back-of-house ops; AI-native by design and built on top of Claude; Series A momentum backed by Khosla Ventures