Manager and Director of AI Strategy (several available - fully remote)

Hiring several of both positions due to rapid growth! Manager of AI Strategy Director of AI Strategy (Client facing, leading accounts, activations etc) Remote - $120k - $160k base + bonus/commission 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 enterprise 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. (Manager level has similar responsibility however isn't a pod leader and does not have P&L responsibility. Hands on position within the team). Role Overview 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 enterprise 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 enterprise environments. Key Responsibilities AI Strategy & Transformation Leadership Serve as fractional Director of AI Strategy for 5–10 enterprise 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 enterprise environments, 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 Client Ownership & Account Leadership ● 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 Team Leadership & Pod Management ● 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 Delivery & Execution Oversight 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 P&L Management & Business Performance Manage th