VP of AI Strategy

Go Cadre•San Diego, CA

About The Position

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.

Requirements

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; you are comfortable in the room with a CEO and can move a high-stakes conversation with clarity and authority.
Strong commercial instincts and a history of closing or contributing directly to renewal and upsell conversations; you understand that delivery and revenue are connected.
Deep, working knowledge of AI and its practical business applications; you do not need to be an engineer, but you must be able to speak credibly about AI strategy and translate it into roadmaps executives act on.
Experience designing and delivering AI roadmaps, maturity assessments, or use case libraries for mid-market or enterprise clients.
Exceptional written and verbal communication; your deliverables set the quality bar, and your facilitation style builds trust quickly.
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.
Comfort working in a fast-moving, high-ownership environment where the playbook is still being refined and the best ideas come from people who take initiative.

Responsibilities

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.
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 complex findings into clear executive narratives.
Produce polished, insight-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.
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 conversation at the conclusion of each strategy project, owning the transition from fixed-scope engagement to long-term partnership.
Identify scope expansion and upsell opportunities within active engagements and work with pod leaders to ensure clean handoffs when projects convert.
Partner with the velocity sales team to align on what a well-qualified strategy handoff looks like and ensure you are set up to deliver from day one without wasted re-discovery.
Relay client feedback, emerging needs, and expansion signals to the Head of AI Strategy and relevant pod leaders.
Contribute to the continuous improvement of Cadre's strategy methodology, deliverable templates, and execution standards.
Collaborate with engineering and AI tooling to integrate Cadre's internal infrastructure, including prompt libraries, use case databases, and AI-enabled ROI tools, into your workflow.