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

The Director of AI Strategy is a senior, AI-first leader who owns end-to-end AI transformation for a portfolio of 5–10 clients. You serve as their fractional Director of AI Strategy—embedded in their organizations as their most senior AI voice—while leading a cross-functional pod of approximately five AI strategists, engineers, and automation specialists.

This is a leadership role with real P&L accountability. You manage the financial performance of your pod, drive client retention and expansion, lead new sales cycles within existing accounts, and ensure your team delivers exceptional results. You need to speak fluently with C-suite executives, translate business problems into technical solutions, and drive measurable impact across complex environments.

There is no hand-off between strategy and execution here. You own both.

What You’ll Do

Lead AI Strategy and Transformation

Serve as fractional Director of AI Strategy for 5–10 clients, acting as their senior AI leader and strategic advisor
Define and execute AI roadmaps aligned to business goals, operational realities, competitive dynamics, and measurable ROI
Lead strategic discovery and planning sessions to identify, prioritize, and scope high-impact AI and automation opportunities across client organizations
Drive AI transformation across complex organizations, navigating change management, stakeholder alignment, and cross-functional complexity
Translate complex business problems into technical solutions, bridging the gap between executive vision and engineering execution
Stay at the forefront of AI innovation—LLMs, agentic AI, automation platforms—to continuously elevate your strategy and recommendations

Own Client Relationships and Account Growth

Own the full client relationship as the primary senior point of contact and trusted advisor, building deep executive relationships with C-suite and senior leadership
Drive client satisfaction, retention, and long-term value creation through consistent delivery of business impact and strategic guidance
Run client meetings with confidence and precision—executive business reviews, strategy sessions, stakeholder alignment—clearly communicating AI strategy, progress, risks, and outcomes
Identify and lead expansion opportunities within existing accounts, uncovering new use cases, additional business units, and strategic initiatives that can benefit from AI
Own the discovery, scoping, proposal, and closing process for expansion opportunities within your portfolio

Lead and Develop Your Pod

Lead and develop a cross-functional pod of approximately 5 professionals including AI strategists, engineers, and automation specialists
Build a high-performing, collaborative team culture focused on excellence, accountability, and continuous improvement
Manage team performance, coaching, and professional development—providing clear feedback, mentorship, and growth opportunities
Allocate resources strategically across your client portfolio to maximize utilization, impact, and team satisfaction
Set clear priorities, expectations, and deliverables for your team across multiple concurrent client engagements

Drive Delivery and Execution

Oversee end-to-end AI project delivery from discovery and design through implementation, adoption, and optimization
Ensure projects are delivered on time, within scope, and to the highest quality standards—proactively managing risks and dependencies
Lead solution design and prototyping, working closely with engineering teams to ensure AI solutions are practical, scalable, and aligned to client needs
Drive AI adoption and change management, leading or supporting client training, enablement, and organizational adoption initiatives
Track and report on project progress, delivery performance, and business impact using ClickUp as the core project management system

Own P&L and Business Performance

Manage the financial performance of your pod: revenue, utilization, margin, and profitability
Own client retention and revenue growth targets, ensuring your portfolio delivers consistent financial performance
Drive expansion revenue by identifying, scoping, and closing new opportunities within existing client accounts
Optimize resource allocation and utilization to balance delivery excellence with financial efficiency
Participate in performance-based incentives tied to the financial success and growth of your pod

Who You Are

7–10+ years of experience in client-facing businesses or agency environments, with a proven track record of managing multiple client relationships and driving measurable business outcomes
You have led AI or digital transformation initiatives at scale and can point to specific business results—revenue gained, costs saved, processes eliminated
Strong people leadership experience: you’ve built, coached, and retained high-performing technical teams, and you know how to develop people without micromanaging them
P&L accountability is not new to you. You understand how to manage utilization, margin, and revenue growth across a portfolio of accounts
Deep understanding of AI/ML/LLMs, automation, and applied AI—with the ability to translate complex technical concepts into clear business value for C-suite executives
Excessively organized. You run multiple complex engagements simultaneously without dropping the ball, and you use tools like ClickUp to keep everything visible and structured
Exceptional executive presence and communication skills—you’ve run high-stakes client meetings, navigated difficult stakeholder dynamics, and consistently come out as the trusted advisor in the room

What Sets You Apart

You’ve operated as a fractional or embedded strategic leader inside a client organization—not just as an external consultant who shows up with slides
Track record of expansion: you’ve grown accounts, not just retained them. You can walk into an existing relationship and find the next initiative worth pursuing
You move fast and stay organized. Ambiguity doesn’t slow you down—you create structure where there isn’t any
Domain experience in financial services, real estate, private equity, lending, or B2B SaaS
You’ve led teams that include both strategists and engineers—you know how to bridge those worlds and get the best out of each

Why Cadre AI

Real ownership. You run your own book of business with full accountability for strategy, delivery, team, and P&L. This is not a support role.
High-impact work. The AI roadmaps you build and the systems your team ships change how businesses operate. You’ll see the results directly.
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.

Cadre AI is building the future of how companies adopt and operate AI. We believe the best outcomes come from leaders who understand both the business and the technology serving it. If that’s how you think, we want to talk.

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Director of AI Strategy