AI Engagement Lead: Commercial Real Estate, Strategy & C-Suite Advisory | Remote USA (Chicago) | Up to $240K + Equity

"A-B-C. Always Be Compounding."
With apologies to Glengarry Glen Ross, the greatest real estate film ever made. In this seat you don't close a deal and walk away. You land the account, prove the value, and keep growing it.
The opportunity
Commercial real estate is one of the largest asset classes on the planet, and it still runs on spreadsheets, PDFs and phone calls. My client, an early-stage AI company, is building the platform that changes that: taking a firm's documents and data and making them something AI agents can reason over, with traceable, source-backed answers. They already work with some of the most recognized names in CRE.
Now they need one of their first senior client leaders. Someone who has sat across the table from real estate CEOs, understands how an investment committee thinks, and can turn a messy business problem into a brief an engineering team can ship.
What you'll own
Two to three enterprise CRE accounts, as the lead executive contact from the first workshop through to live deployment and expansion
Discovery: stakeholder interviews, process mapping and ranking the use cases that matter, ending in a roadmap, success metrics and a technical brief
The bridge between client and build team, turning business context into clear, testable problem statements for forward deployed engineers
The executive room: running leadership meetings and producing client-ready work that sets expectations and holds them
Delivery: guiding each engagement through build, launch and adoption, measured against what was agreed
Account growth: spotting the next use case, building the expansion plan, and writing the delivery playbooks
What you bring
Commercial real estate experience (essential): you've worked at a CRE firm in investment, lending, asset management, development or operations, or advised real estate clients directly
6+ years in senior strategy work: Engagement Manager level (or equivalent) at McKinsey, Bain, BCG or another strategy house, private equity portfolio work, or leading AI strategy inside a company
C-suite presence with CEOs and leadership teams at $1B to $50B+ real estate firms
A record of growing accounts well beyond their original scope
Ready to travel around 40% of the time to client sites
Steady tenure, not a run of short stints
Bonus points
You've led or bought an AI initiative inside a real estate firm
Series A to C startup experience
This one probably isn't for you if
Your background is mainly customer success or account management rather than leading engagements
Your consulting experience is IT or systems implementation rather than strategy
The package
Up to $240K base, plus meaningful early-team equity
Remote within US time zones. The core team is in Chicago and Chicago-based candidates are preferred, but the best person wins
Live near a major airport, as client travel runs at roughly 40 to 50%
In-person team get-togethers a few times a year
US citizens and Green Card holders only. No visa sponsorship and no relocation support
Why this one
A strategy seat with builders behind you: you set the roadmap, forward deployed engineers and a shared AI platform ship it in weeks
Leaders who know real estate from the inside
Investors with deep roots in real estate, which means warm access to the firms it sells to
Shape the delivery model as one of the first client leaders
A vertical with no clear winner yet, so you build real domain authority as the category forms
How to apply
Apply with your resume and a few lines on the most complex real estate engagement you've led, and what grew out of it.
Keywords: Commercial Real Estate, CRE, Real Estate Investment, Asset Management, Real Estate Private Equity, Proptech, Engagement Manager, Strategy Consulting, Management Consulting, McKinsey, Bain, BCG, Private Equity, AI Strategy, Enterprise AI, Digital Transformation, Client Engagement, C-Suite Advisory, Executive Stakeholder Management, Account Expansion, Process Mapping, Product Roadmap

Skills
Account Management, Customer Success

Experience
8+ yrs

Work arrangement
Yes