AI Strategy Enablement Lead

AI Strategy Enablement Lead

Req number:

R7982

Employment type:

Full time

Worksite flexibility:

Remote

Who we are

CAI is a global services firm with over 9,000 associates worldwide and a yearly revenue of $1.3 billion+. We have over 40 years of excellence in uniting talent and technology to power the possible for our clients, colleagues, and communities. As a privately held company, we have the freedom and focus to do what is right—whatever it takes. Our tailor-made solutions create lasting results across the public and commercial sectors, and we are trailblazers in bringing neurodiversity to the enterprise.

Job Summary

We are looking for a motivated AI Strategy Enablement Lead ready to take us to the next level! If you have experience driving hands-on execution of AI transformation and are looking for your next career move, apply now.

Job Description

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. This is a full-time position and fully remote within the United States.

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.

What You’ll Do

• 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

What You’ll Need

Required:

• 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

Preferred:

• 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

What Sets This Role Apart

This is not a strategy-on-paper role and it is not a technology implementation role. It is the execution role that determines whether CAI’s AI strategy becomes real. You will not be building AI models or writing production code — you will be running the initiative that turns enterprise AI ambition into working capability and measurable outcomes.

The right person is a builder with consulting discipline: comfortable owning the mechanics of a complex, multi-workstream program, fluent enough in AI to lead the working conversation, and credible enough to keep senior stakeholders aligned and moving. You will have real autonomy over how the work gets done, in an environment where the results are visible and the work matters.

Physical Demands

• Ability to safely and successfully perform the essential job functions consistent with the ADA and other federal, state and local standards 

• Sedentary work that involves sitting or remaining stationary most of the time with occasional need to move around the office to attend meetings, etc. 

• Ability to conduct repetitive tasks on a computer, utilizing a mouse, keyboard, and monitor 

#LI-GR1

Reasonable accommodation statement

If you require a reasonable accommodation in completing this application, interviewing, completing any pre-employment testing, or otherwise participating in the employment selection process, please direct your inquiries to application.accommodations@cai.io or (888) 824 – 8111.

EEO Statement

It is the policy of Computer Aid, Inc.(CAI) not to discriminate against any employee or applicant for employment because of race, color, religion, sex, sexual orientation, gender identity, national origin, age, marital status, genetic information, disability or because he or she is a protected veteran. It is also the policy of CAI to take affirmative action to employ and to advance in employment, all persons regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, marital status, genetic information, disability or protected veteran status, and to base all employment decisions only on valid job requirements. This policy shall apply to all employment actions, including but not limited to recruitment, hiring, upgrading, promotion, transfer, demotion, layoff, recall, termination, rates of pay or other forms of compensation and selection for training, including apprenticeship, at all levels of employment.

 

Employees and applicants of CAI will not be subject to harassment on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, marital status, genetic information, disability or because he or she is a protected veteran. Additionally, retaliation, including intimidation, threats, or coercion, because an employee or applicant has objected to discrimination, engaged or may engage in filing a complaint, assisted in a review, investigation, or hearing or have otherwise sought to obtain their legal rights under any Federal, State, or local EEO law is prohibited.

$175,000 - $200,000 per year

The pay range for this position is listed above. Exact compensation may vary based on several factors, including location, experience, and education. Benefit packages include medical, dental, and vision insurance, as well as 401k retirement account access. Employees in this role receive paid time off and may also be entitled to paid sick leave and/or other paid time off as provided by applicable law.