VP of AI Strategy

• 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.

• 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.

• 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.

Compensation