VP of AI Strategy
AI summary of the role
Cadre AI seeks a VP of AI Strategy to own the full lifecycle of AI strategy engagements for B2B clients, from kickoff to delivery, and to convert completed projects into long-term retainers.
What you’ll do
- Own AI strategy engagements end-to-end, from sales handoff through final delivery, with full accountability for scope, timeline, and client satisfaction.
- Lead discovery engagements including stakeholder interviews, workflow assessments, and AI readiness evaluations to surface high-impact opportunities.
- Develop comprehensive AI roadmaps that prioritize use cases by feasibility, ROI, and strategic alignment, and translate findings into executive narratives.
- Facilitate client workshops and working sessions independently, moving groups from ambiguity to clarity.
What you’ll bring
- 8+ years of experience in management consulting, AI strategy, or business advisory work, with a track record of leading client engagements from kickoff through delivery.
- 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.
Technologies
AI strategy · ClickUp · AI readiness · ROI tools · prompt libraries · use case databases
Source and classification
Deployment strategy · Evidence for this classification:
About Cadre AI Cadre AI is an AI strategy and integration firm that partners deeply with organizations to transform workflows, streamline operations, and deliver measurable business outcomes. We operate at the intersection of strategy, engineering, and adoption—ensuring AI delivers real, lasting impact for the B2B companies we serve. The Role As VP of AI Strategy, you are one of a small number of senior individual contributors who form the backbone of Cadre's strategy practice. You own the full lifecycle of AI strategy engagements, from kickoff through final delivery, and you are personally accountable for converting completed projects into long-term retainers. There is no hand-holding, no co-pilot, and no safety net. You run the room, earn the trust, and close the next chapter. You will engage directly with C-suite stakeholders, lead workshops and working sessions independently,
More from the job description
About Cadre AI Cadre AI is an AI strategy and integration firm that partners deeply with organizations to transform workflows, streamline operations, and deliver measurable business outcomes. We operate at the intersection of strategy, engineering, and adoption—ensuring AI delivers real, lasting impact for the B2B companies we serve. The Role As VP of AI Strategy, you are one of a small number of senior individual contributors who form the backbone of Cadre's strategy practice. You own the full lifecycle of AI strategy engagements, from kickoff through final delivery, and you are personally accountable for converting completed projects into long-term retainers. There is no hand-holding, no co-pilot, and no safety net. You run the room, earn the trust, and close the next chapter. 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. When you sit down with a client at the end of an engagement, you own that retainer conversation. Your ability to build trust, connect roadmap priorities to ongoing needs, and close confidently is a core part of what this role requires. 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 [... source excerpt omitted ...] ake it. What You'll Do Engagement Ownership Own AI strategy engagements end to end, from sales handoff through final delivery, with full accountability for scope, timeline, and client satisfaction. Lead structured onboarding sessions that establish project scope, success criteria, key stakeholders, and working rhythms from day one. Manage all project infrastructure in ClickUp in coordination with the Operations Specialist, including tasks, milestones, timelines, and client-facing naming conventions. Proactively flag risks, manage scope, and ensure on-time, on-budget delivery across every active engagement. Strategy Execution and Delivery Lead discovery engagements inclu [... source excerpt omitted ...] ght-driven deliverables including discovery findings, opportunity assessments, implementation roadmaps, and executive presentations that meet Cadre's quality standard. Facilitate client workshops and working sessions independently, moving groups from ambiguity to clarity with confidence. Retainer Conversion Build trusted advisor relationships with client stakeholders throughout each engagement by demonstrating genuine investment in their outcomes and deep AI expertise. Connect roadmap priorities to the ongoing support a long-term retainer provides, positioning Cadre's Solutions offering as the natural next step rather than a sales pitch. Lead the retainer close conversatio
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