CRE AI Strategy Lead - Enterprise Growth & C-Suite Advisory

Big Wave Digital - USA; Chicago (IL); Remote; USD 216,000 - 264,000; Full time

Job summary

Big Wave Digital - USA is seeking a senior client leader to guide enterprise CRE engagements from inception through deployment and expansion. You will bridge client strategy with forward-deployed engineering, lead executive discussions, and shape delivery playbooks across complex real estate deals.

You will sit with CEOs and leadership teams, driving account growth and defining roadmaps with measurable success metrics. Remote within US time zones, preferably Chicago-based, with ~40% travel.

Qualifications

• Commercial real estate experience at a CRE firm or advising clients directly.
• 6+ years in senior strategy work (Engagement Manager level or equivalent).
• C-suite presence with CEOs and leadership teams at large real estate firms.
• Proven track record of growing accounts beyond original scope.
• Willingness to travel ~40% to client sites.
• Steady tenure with longer engagements.
• Led or bought an AI initiative inside a real estate firm.
• Series A to C startup experience.

Responsibilities

• Lead 2–3 enterprise CRE accounts from first workshop to deployment and expansion.
• Conduct discovery: stakeholder interviews, process mapping, and use-case ranking to create roadmaps and success metrics.
• Translate client context into clear, testable problem statements for engineers.
• Run leadership meetings and produce client-ready work to set expectations and guide delivery.
• Guide engagements through build, launch, and adoption, measuring against agreed outcomes.
• Identify expansion opportunities, craft expansion plans, and document delivery playbooks.

Skills

Commercial real estate experience

Senior strategy experience

C-suite presence

Account growth

Travel readiness

Stable tenure

AI initiative leadership

Startup exposure (Series A–C)

Job description

Big Wave Digital - USA is seeking a senior client leader to guide enterprise CRE engagements from inception through deployment and expansion. You will bridge client strategy with forward-deployed engineering, lead executive discussions, and shape delivery playbooks across complex real estate deals.

You will sit with CEOs and leadership teams, driving account growth and defining roadmaps with measurable success metrics. Remote within US time zones, preferably Chicago-based, with ~40% travel.