Full Time
$5-9.00/hour USD
40
Sep 11, 2026
About the Role
We are a Chicago-focused real estate development company seeking a highly resourceful, analytical, and persistent person to help us find and evaluate development opportunities. This role combines deal sourcing, owner research, direct outreach, zoning research, and real estate underwriting. It is not a traditional administrative VA role.
Your job is simple to describe but difficult to master: find properties that may be valuable development opportunities, reach the decision makers, and learn how to determine whether the economics make sense.
What You Will Do
• Search for on-market and off-market development opportunities throughout targeted Chicago neighborhoods.
• Identify vacant land, parking lots, underutilized commercial properties, redevelopment sites, distressed buildings, and properties with substantially more development potential than their existing use.
• Research property ownership and find the actual decision maker, including phone numbers, emails, mailing addresses, related entities, debt information, tax information, and other useful data.
• Conduct targeted phone, email, and direct-mail outreach to owners on behalf of a real estate developer.
• Track follow-ups persistently and professionally.
• Research Chicago zoning and calculate lot area, FAR, buildable area, approximate unit potential, parking, ARO/TOD considerations, and potential rezoning scenarios.
• Screen deals using land cost per unit, location, zoning, physical feasibility, achievable rents, and development economics.
• Use our underwriting model to analyze rents, NOI, development cost, financing, yield on cost, refinance proceeds, and cash recycling.
• Maintain a clean CRM/pipeline of every property, owner interaction, next action, and underwriting result.
• Identify smaller deals that may be appropriate to wholesale to other developers.
How You Will Spend Your Time
This is a full-time, eight-hour-per-day role. When there are real deals to analyze, you will analyze them. When there are not, you will source. There should always be another productive action: research a property, find an owner, send an email, make a targeted call, follow up, review zoning, research debt/taxes, or improve the pipeline.
What We Are Looking For
• Excellent analytical ability and comfort with numbers.
• Strong internet research skills and persistence in finding hard-to-locate information.
• Ability to learn complicated rules and apply them to real situations.
• Strong written and spoken English.
• Comfort speaking with property owners by phone and email.
• Organized, detail-oriented, and disciplined about follow-up.
• Independent problem solver who does not stop when the first search fails.
• Comfort with spreadsheets and willingness to learn real estate underwriting.
• Good judgment: you should be able to understand that a cheap property is not always a good deal and an expensive property is not always a bad deal.
Helpful but Not Required
• Real estate, finance, underwriting, brokerage, property research, or acquisitions experience.
• Experience with zoning, GIS/maps, property databases, skip tracing, CRM systems, or cold outreach.
• Experience analyzing multifamily, land, or development deals.
What Success Looks Like
• You progressively learn to look at an address and recognize whether it deserves attention.
• You bring ownership qualified opportunities instead of simply sending random listings.
• You know when a property should be rejected, followed up, wholesaled, fully underwritten, or escalated immediately.
• Your pipeline stays active because every viable owner is followed up until there is a definitive answer.
• Over time, you require less direction because you learn how we think about location, zoning, price, unit potential, rents, and development returns.