User testing Jobs in Chicago, IL

Manager of AI User Enablement

We're building a world of health around every individual shaping a more connected, convenient and compassionate health experience. At CVS Health, you'll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger helping to simplify health care one person, one family and one community at a time.

As a Manager of AI User Enablement, you will be the field-facing lead for how the Pharmacy Services Finance organization learns to work with AI. As part of Finance Intelligence within PS Finance Technology Enablement, this role will allow you to work shoulder to shoulder with finance professionals across various verticals teaching, coaching, and curating the training and communications that turn AI curiosity into confident, everyday practice.

PS Finance colleagues are already using AI tools; what varies is how well, how consistently, and how safely. This role closes that gap not by building AI solutions, and not by writing policy, but by building literacy, curating learning materials, and developing momentum that lets colleagues solve the problems in front of them, both with the tools they already have and with the constant supply of new product entries.

This role is designed for a natural teacher and communicator who is energized by being in the field. The right candidate is a current or emerging expert in hands-on AI use within business settings, and is motivated by the chance to shape a brand-new enablement program at a moment when the mandate is both clear and urgent.

Primary Functions and Areas of Ownership

• Act as a "forward-deployed analyst," partnering with Finance business units on adoption: observing workflows, spotting opportunities, and supporting leaders in role modeling responsible AI use.
• Partner with training and communications teams on a role-based AI enablement curriculum, to include training sessions, demonstrations, workshops, embedded coaching, hackathons, and lunch-and-learns, focused on building demonstrated capability.
• Support build and maintenance of prompt libraries, agent examples, use-case patterns, and plain-language guides.
• Establish a practitioner community and champion network; surface literacy gaps, adoption barriers, and emerging misuse to the Lead Director and advisory councils.
• Support design and delivery of user surveys; translate results into user journey maps, and design enablement strategies for each user profile they reveal.
• Measure adoption and learning effectiveness reach, capability, sustained workflow use; set baselines and report where usage has not become capability.
• Improve the program on evidence, converting recurring one-off coaching into reusable assets.
• Coordinate with governance, product, and business stakeholders; support the operating cadence and keep training aligned to standards you do not own.

What success looks like in this role

• PS Finance colleagues can solve the problems in front of them with the tools they have, confidently, efficiently, and in a way that aligns with how the organization intends to work.
• A practitioner communication and champion network are functioning, engaged, and effective; with role-based curriculum, dependable working session rhythm, and a reusable asset library established and in active use.
• Enablement communications are current, findable, and tied to concrete actions; colleagues understand what AI Enablement is, where to access resources, and how to engage with both AI products the AI Enablement team.
• Adoption and learning effectiveness are measured against defined baselines, and the enablement program visibly changes in response to what those measures show.
• The organization treats this role as its primary contact for hands-on support with desktop business AI tools, such as Copilot and Claude Enterprise.

What this role is not

• This is not an AI engineering, data science, or solution architecture role. AI User Enablement coaches and advises, supporting appropriate owners in solution development.
• This role is not the owner of governance policy or product management though the insights they obtain from working in the field are vital to related feedback loops.

Required Qualifications

• 5 + years of relevant work experience.
• Expert communication and facilitation skills, with experience coordinating live workshops or working sessions for professional audiences, including senior stakeholders.
• 3 + years of experience designing and delivering training, enablement, communications, or organizational change programs for business audiences.
• 2 + years of experience driving adoption and behavior change across teams and stakeholder groups without direct authority.
• 1 + years of experience with AI enablement, project management of AI solutions, or similar advanced technology deployed in a business environment.
• Deep, demonstrable expertise with Microsoft Copilot and Claude Desktop/Cowork, and expert proficiency with Microsoft Office applications, critically PowerPoint and presentation design best practices.
• Able to clearly articulate differences in Copilot, Claude Desktop, and Claude Cowork and can demonstrate effective use of each.
• Demonstrated experience translating complex or technical concepts into plain language that non-technical professionals can act on.
• Ability to travel up to 10% (including by plane).

Preferred Qualifications

• Adept at training curriculum design, role-based learning path development, and professional learning delivery.
• Familiarity with structured change management methodology such as ADKAR or a comparable framework.
• Adept at Confluence, SharePoint, or comparable document and knowledge repository platforms; familiarity with Jira or a comparable Kanban-style task management tool.
• Verifiable Microsoft certification or applied-skills credential related to Copilot strongly preferred, including proficiency with Copilot Studio.

Education

• Required: Bachelor's Degree or equivalent years of related professional work experience
• Preferred: Master's degree in AI, organizational leadership, education, communications, or a related field

Anticipated Weekly Hours

40

Time Type

Full time

Pay Range

The typical pay range for this role is:

$66,330.00 - $145,860.00

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

This full?time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well?being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

Additional details about available benefits are provided during the application process and on Benefits Moments.

We anticipate the application window for this opening will close on: 10/17/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.