VP of AI Strategy

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 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.

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 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.

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 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.

Cross-Functional Collaboration

• 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.

What You Need to Succeed

• 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.

Why Cadre AI

• Full ownership from day one. You are not supporting someone else's engagement. You run it, own it, and close it. That level of autonomy is rare.
• Direct commercial impact. Your retainer conversion rate feeds Cadre's growth trajectory directly. The work you do is not abstract; it shows up on the scoreboard.
• AI-native from the inside out. You will not just advise clients on AI adoption; you will work in an environment where AI is embedded in how we operate, build, and deliver.
• A small team of serious people. Cadre is a high-trust, high-output organization. There is no bureaucracy, no layers, and no politics between you and the work that matters.
• Room to grow. As the strategy practice scales, so does this role. VP of AI Strategy is a critical seat with a long runway for the right person.

Competitive compensation plan - OTE $200-300K