AI Engagement Lead: Commercial Real Estate, Strategy & C-Suite Advisory | Remote USA (Chicago) | Up

"A-B-C. Always Be Compounding."

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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.

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The opportunity

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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.

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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.

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What you'll own

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• Two to three enterprise CRE accounts, as the lead executive contact from the first workshop through to live deployment and expansion
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• Discovery: stakeholder interviews, process mapping and ranking the use cases that matter, ending in a roadmap, success metrics and a technical brief
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• The bridge between client and build team, turning business context into clear, testable problem statements for forward deployed engineers
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• The executive room: running leadership meetings and producing client-ready work that sets expectations and holds them
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• Delivery: guiding each engagement through build, launch and adoption, measured against what was agreed
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• Account growth: spotting the next use case, building the expansion plan, and writing the delivery playbooks
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What you bring

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• 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
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• 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
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• C-suite presence with CEOs and leadership teams at $1B to $50B+ real estate firms
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• A record of growing accounts well beyond their original scope
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• Ready to travel around 40% of the time to client sites
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• Steady tenure, not a run of short stints
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Bonus points

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• You've led or bought an AI initiative inside a real estate firm
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• Series A to C startup experience
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This one probably isn't for you if

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• Your background is mainly customer success or account management rather than leading engagements
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• Your consulting experience is IT or systems implementation rather than strategy
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The package

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• Up to $240K base, plus meaningful early-team equity
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• Remote within US time zones. The core team is in Chicago and Chicago-based candidates are preferred, but the best person wins
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• Live near a major airport, as client travel runs at roughly 40 to 50%
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• In-person team get-togethers a few times a year
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• US citizens and Green Card holders only. No visa sponsorship and no relocation support
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Why this one

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• A strategy seat with builders behind you: you set the roadmap, forward deployed engineers and a shared AI platform ship it in weeks
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• Leaders who know real estate from the inside
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• Investors with deep roots in real estate, which means warm access to the firms it sells to
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• Shape the delivery model as one of the first client leaders
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• A vertical with no clear winner yet, so you build real domain authority as the category forms
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How to apply

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Apply with your resume and a few lines on the most complex real estate engagement you've led, and what grew out of it.

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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