Responsibilities
- Own both sides of the transaction - acquisitions and dispositions
- Work quickly to put together and present offers
- Negotiate ruthlessly on behalf of our customers
- Manage listings end-to-end: getting them active, fielding and negotiating offers, and keeping deals together from contract to close
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
- 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
- SFR or institutional experience
- Licenses in additional states beyond the minimum requirement
Benefits
- Base salary starts at $50,000 with on-target earnings of $113,000+
- Equity in Mainstay
- Dedicated pricing, field visits, and transaction coordination teams
- AI-augmented stack that handles HOA/tax workflows and back-of-house ops
Work Arrangement
Remote (City/Region) — Chicago
Additional Information
- Real estate doesn't sleep. Nights and weekends come with the territory.
- Fully remote within the United States
- 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
