AI Strategy Enablement Lead

CAI•,

2d•$175,000 - $200,000•Remote

About The Position

We are hiring an AI Strategy Enablement Lead to drive the hands-on execution of CAI’s enterprise AI transformation. This is a builder’s role. You will take the AI strategy set by executive leadership and make it operational — standing up the workstreams, running the cadence, producing the deliverables, and shepherding initiatives from concept through adoption across CAI’s core business functions. You will sit within CAI’s Strategy & Operations function and serve as the day-to-day execution engine for CAI’s AI strategy program. This work spans internal AI transformation across CAI’s business functions, AI-driven evolution of our go-to-market service lines, and the development of new AI-enabled offerings. You will own the execution mechanics — the roadmaps, the tracking, the artifacts, the follow-through — and ensure the program produces measurable outcomes rather than slide decks. This is a high-visibility individual-contributor role with significant autonomy over how the work gets done. You will partner closely with the AI Steering Committee, the AI Strategy Leadership team, and cross-functional stakeholders, orchestrating the cadence and surfacing the decisions, risks, and trade-offs that leadership needs to act on. You will pressure-test timelines, flag blockers early, and keep the transformation moving.

Requirements

5+ years of experience in management consulting, enterprise transformation, or AI/digital strategy and delivery.
Demonstrated experience executing enterprise transformation or AI/digital initiatives hands-on — building roadmaps, running the cadence, and driving work through to adoption, not advisory only.
Working knowledge of the AI landscape: large language models, agentic AI, enterprise AI platforms, data strategy, and AI governance frameworks.
Strong project and program management skills, including roadmap and project-plan development, RAID management, and executive reporting.
Proven ability to operate in complex stakeholder environments up to the C-suite and senior VP level, coordinating competing priorities and navigating organizational resistance.
Ability to assess AI tools and technical approaches with informed judgment — technical enough to challenge assumptions, practical enough to prioritize what matters.
Exceptional written and verbal communication skills — able to facilitate workshops and produce high-quality, executive-ready deliverables.
Advanced proficiency with Microsoft Office, particularly PowerPoint, Excel, and Visio.
Bachelor’s degree required; MBA or advanced degree preferred.
Must be legally authorized to work in the United States without the need for employer sponsorship, now or at any time in the future.

Nice To Haves

Experience in public sector, state and local government, or government-adjacent industries.
Familiarity with government procurement dynamics, compliance frameworks (FedRAMP, GovRAMP), and the structural constraints of public sector AI adoption.
Experience with AI-driven workforce transformation, including change management, productivity measurement, and upskilling program design.
Hands-on familiarity with Anthropic’s Model Context Protocol (MCP), agentic AI frameworks, or enterprise AI orchestration platforms.
Transformation experience across procurement, sourcing (S2P), or related functions.
Track record of designing and piloting operating models, governance structures, and performance frameworks.

Responsibilities

Translate executive AI strategy into actionable roadmaps with clear milestones, owners, deliverables, and success criteria, then drive the work day to day
Own the execution mechanics of the enterprise AI program end to end — sequencing workstreams, managing interdependencies, and coordinating resources across business lines and corporate functions
Drive AI initiatives across enterprise functions from discovery and roadmap through deployment and adoption, producing measured outcomes that become transferable assets for CAI’s client-facing offerings
Build the executive-ready artifacts that move the program forward: roadmaps, business cases, use-case prioritization, status reporting, process workflows, and decision materials
Run the operating cadence of the AI program: schedule and prepare for working sessions and steering reviews, capture decisions and actions, and track commitments to closure
Prepare materials for the AI Steering Committee, facilitate working sessions, and surface decisions and blockers to leadership for resolution
Coordinate across the AI Steering Committee and AI Strategy Leadership to align execution with enterprise priorities
Surface resistance and organizational friction early, and escalate trade-offs and risk with clarity so leadership can decide and act
Support the design and implementation of target-state operating models for AI-enabled ways of working — spanning process, roles, governance, and performance measures
Identify where out-of-the-box AI solutions apply and where custom integration or workflow redesign is required, ensuring CAI avoids the trap of layering AI onto broken processes
Manage program risk through structured RAID tracking, and put light-weight controls in place to keep initiatives on track
Document processes, build playbooks, and educate internal teams on AI-enabled leading practices so capability sticks after each initiative closes
Maintain current, working knowledge of the enterprise AI landscape: LLMs, agentic frameworks, MCP architecture, AI governance standards, and emerging tools
Apply hands-on fluency with AI tools to accelerate analysis, automate routine work, and raise the quality and speed of program deliverables
Bring an informed, evidence-based perspective on what AI can and cannot do today to keep initiatives grounded and realistic
Ensure internal AI initiatives map to external go-to-market opportunities — internal transformation is the evidence base for CAI’s client-facing AI offerings.
Package internal AI results into reusable inputs for client-ready case studies, RFP content, and thought leadership in partnership with sales and marketing