AI Engagement Lead: Commercial Real Estate, Strategy Consulting & 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 engineers can build from

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, including the conversations where the answer is "not yet"

Delivery: guiding each engagement through build, launch and adoption, and measuring results against what was agreed

Account growth: spotting the next use case, building the expansion plan, and writing the playbooks for how the company delivers

What you bring

Commercial real estate experience (essential). You've worked at a CRE firm in investment, lending, asset management, development or operations, or you've 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. You're comfortable running the room 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. A career built on real engagements, not a run of short stints

Bonus points

You've led or bought an AI initiative inside a real estate firm. If you've been the buyer, you already know what works and what doesn't

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, which is a big part of the upside here

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 turn it into working software in weeks, not quarters

Leaders who know real estate from the inside, with deep operating, investing and finance backgrounds across the industry

Doors already open. The company is backed by investors with deep roots in real estate, which means warm access to the firms it sells to

Build the model. As one of the first client leaders, you'll shape how the company engages, delivers and grows accounts

A vertical with no clear winner yet. CRE is huge, relationship-driven and early in its AI journey. This is a chance to build real domain authority as the category forms

How to apply

Apply using the form on this page. Include a few lines on the most complex real estate engagement you've led and what grew out of it, plus your salary expectation and confirmation that you are a US citizen or Green Card holder.