Director of AI Strategy

Go Cadre•San Diego, CA

3h•Onsite

About The Position

At Cadre AI, we help organizations unlock the power of artificial intelligence to transform workflows, streamline operations, and deliver measurable business outcomes. We operate at the intersection of strategy, engineering, and adoption, partnering deeply with our clients to ensure AI delivers real, lasting impact We are seeking a Director of AI Strategy to serve as a senior client-facing leader and fractional Director of AI Strategy for a portfolio of clients. This role combines strategic leadership, client ownership, team management, P&L accountability, and business development. You will lead a high-performing pod of AI strategists and engineers while driving transformational AI initiatives that deliver measurable business value and expand client relationships. The Director of AI Strategy is a senior, AI-first leader responsible for owning and executing end-to-end AI transformation for a book of 5–10 clients. You will serve as their fractional Director of AI Strategy, acting as the strategic AI leader embedded within their organizations, while simultaneously managing a cross-functional delivery team of ~5 individuals including AI strategists, engineers, and automation specialists. This is a leadership role with P&L accountability. You will 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. Success requires someone who can speak fluently with C-suite executives, translate business challenges into technical solutions, lead and develop high-performing teams, and drive measurable business impact across complex environments.

Requirements

7–10+ years of experience in client-based businesses or agency environments, with a proven track record of managing multiple client relationships, leading AI or digital transformation initiatives, and driving measurable business outcomes
Strong leadership and people management skills, including experience building, coaching, and retaining high-performing technical teams across concurrent client engagements, with accountability for P&L management, revenue growth, and profitability
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 and bridge the gap between business problems and technical solutions
Excessively organized with exceptional project and program management skills, including proficiency with ClickUp and the ability to maintain structured workflows, clear documentation, and seamless execution across multiple complex client engagements
Excellent communication and executive presence, with proven experience driving client retention, expansion, and new sales cycles, running strategic client meetings, and positioning yourself as a trusted strategic advisor to senior leadership

Responsibilities

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 organizational change, 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, including LLMs, agentic AI, automation platforms, and applied AI trends, to continuously elevate strategy and recommendations
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, including executive business reviews, strategy sessions, and stakeholder alignment meetings, 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
Drive new sales cycles within client accounts, owning the discovery, scoping, proposal, and closing process for expansion opportunities
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
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, maintaining structured workflows and documentation
Manage the financial performance of your pod, including revenue, utilization, margin, and profitability metrics
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
Help define and refine Cadre AI's AI strategy, delivery standards, and best practices, contributing to the evolution of our methodologies and frameworks
Ensure excessively organized execution across all client engagements, maintaining clear documentation, structured workflows, and transparent communication
Collaborate with other Directors and senior leadership to share learnings, align on company strategy, and drive operational improvements
Contribute to thought leadership, content creation, and industry positioning that strengthens Cadre AI's reputation and market presence