Director of AI Strategy (Copy)

Go Cadre • San Diego, CA

1d • Hybrid

About The Position

The AI Consultant is a senior individual contributor on Cadre AI’s Strategy
Organization. You own the end-to-end execution of fixed-scope AI strategy
engagements—from kickoff through final delivery—and you set the stage for
clients to take the next step into a long-term retainer.
This role requires cross-vertical business experience, strategic thinking, deep
AI expertise, and complete project ownership. You partner with clients to define
AI roadmaps, deliver high-impact findings, and position Cadre AI as their
long-term transformation partner.
You are not handing work off to someone else. You run the engagement, earn the
trust, and close the next chapter.

Requirements

• 5–10 years of experience in management consulting, AI strategy, or client-facing advisory roles, with a strong track record of independently owning and delivering projects from kickoff through final delivery
• A daily, self-directed practitioner of AI, LLMs, and automation—you stay current not because you have to, but because you’re genuinely obsessed with where this technology is going
• Deep understanding of business processes and the ability to take complex operational problems and make them simple for clients
• Exceptional verbal and written communication skills with strong executive presence—you’ve facilitated workshops, run stakeholder interviews, and presented to C-suite audiences
• Highly organized with strong attention to detail and reliable follow-through across multiple concurrent engagements
• Consultative instinct and commercial awareness—you know how to build client trust, identify the right moment to introduce next steps, and position continued engagement as the natural path forward
• Fluent with Google Workspace, Slack, and ClickUp—proactive, self-directed, and motivated by helping clients move faster and think bigger
• First principles thinker who brings perspective and opinions while staying sensitive to context and skilled at surfacing critical assumptions
• Genuinely energized by rapid change—the pace at which AI is evolving doesn’t intimidate you, it’s why you’re here

Nice To Haves

• You’ve closed the next phase of an engagement yourself—you know how to turn a project relationship into a long-term partnership without it feeling like a sales motion
• Track record of delivering AI strategy work that led to real implementation, not just a deck that got filed away
• You’ve worked across multiple verticals and can get up to speed on a new industry quickly—you ask the right questions before making assumptions
• Systems thinker who is always improving the methodology, not just executing it—you leave every engagement better than you found it
• You move with urgency. You understand that time means impact, and you don’t wait to be told when something needs to happen

Responsibilities

• KICK OFF AND ONBOARD NEW ENGAGEMENTS
• Receive and kick off new strategy engagements handed off from the Sales team, ensuring clients feel confident in Cadre AI’s process from day one
• Lead structured onboarding sessions that establish project scope, success criteria, key stakeholders, and working rhythms
• Set up and maintain all project infrastructure in ClickUp—tasks, milestones, timelines, and client-facing naming conventions—in coordination with the Operations Specialist
• EXECUTE STRATEGY ENGAGEMENTS
• Lead structured discovery engagements: stakeholder interviews, workflow assessments, and AI readiness evaluations to uncover high-impact opportunities
• Develop comprehensive AI roadmaps that prioritize use cases by feasibility, ROI, and strategic alignment, translating complex findings into clear executive narratives
• Produce polished, insight-driven deliverables including discovery findings, opportunity assessments, implementation roadmaps, and executive presentations
• Manage project timelines, scope, and client expectations with precision—proactively flagging risks and ensuring on-time, on-scope delivery
• Facilitate client working sessions, workshops, and milestone reviews with confidence and clarity
• CLOSE THE RETAINER AND HAND OFF
• Build trusted advisor relationships with client stakeholders throughout each engagement, demonstrating deep AI expertise and genuine investment in their outcomes
• Connect roadmap priorities to the ongoing support a long-term retainer provides—positioning Cadre AI’s Solutions offering naturally, not as a sales pitch
• Lead the retainer close conversation at the conclusion of each strategy project, framing the transition as the logical next step
• Document and hand off completed engagements to the Solutions team with thorough context, ensuring a seamless client experience
• COLLABORATE CROSS-FUNCTIONALLY
• Work closely with Directors of AI Strategy, the Operations Specialist, and Engineering pod members to ensure seamless execution across all active engagements
• Relay client feedback, emerging needs, and expansion signals to the Chief Strategy Officer and relevant pod leaders
• Contribute to the continuous improvement of Cadre AI’s strategy methodology, deliverable templates, and project execution standards

Benefits

• Real ownership. You run engagements end-to-end. No handoffs mid-project, no waiting on approvals. You own the outcome.
• Variety and velocity. Every engagement is a different industry, a different problem, and a new chance to build something that matters. You won’t get bored.
• AI-native culture. We don’t just build AI for clients. We use it to run our own operations. You’ll work with people who are as obsessed with the tools as you are.
• Access to the frontier. Through partnerships with Anthropic, OpenAI, and YC, you’ll be among the first to experiment with new models and capabilities.
• Upside. We’re bootstrapped, profitable, and growing fast. Early team members share in the success they help create.
• No bureaucracy. Small pods. Clear accountability. The best idea wins, regardless of who says it.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed