VP of AI Strategy

Cadre
San Diego, CA
Category Operations
Remote
Job Description
Role Overview

As VP of AI Strategy, you will own the full lifecycle of AI strategy engagements, from kickoff through final delivery, and be personally accountable for converting completed projects into long-term retainers. You will engage directly with C-suite stakeholders, lead workshops and working sessions independently, and produce executive-grade deliverables that make the path to ROI undeniable.

What You Will Do

You will own AI strategy engagements end to end, lead structured onboarding sessions, manage project infrastructure, proactively flag risks, and ensure on-time, on-budget delivery across every active engagement. You will also lead discovery engagements, develop comprehensive AI roadmaps, produce polished deliverables, facilitate client workshops, and build trusted advisor relationships with client stakeholders.

Why It Might Be a Fit

The right person has deep consulting experience, commercial instincts, and the ability to move fast without sacrificing quality. You have sat across from executives, facilitated difficult conversations, and built deliverables that clients actually act on. You do not wait to be told what to do next; you see the path and take it.

Requirements

  • 8+ years of experience in management consulting, AI strategy, or business advisory work
  • Demonstrated ability to engage and influence C-suite stakeholders
  • Strong commercial instincts and a history of closing or contributing directly to renewal and upsell conversations
  • Deep, working knowledge of AI and its practical business applications
  • Experience designing and delivering AI roadmaps, maturity assessments, or use case libraries for mid-market or enterprise clients
  • Exceptional written and verbal communication
  • Proven ability to manage multiple active engagements simultaneously without dropping quality, timeline, or client relationship
  • Operator mindset; you see process gaps and fix them, flag risks before they become problems, and take full ownership of your work without waiting to be asked

Benefits

  • Full ownership from day one
  • Direct commercial impact
  • AI-native from the inside out
  • A small team of serious people
  • Room to grow
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