Director, Enterprise AI Enablement

About the role

The Director, Enterprise AI Enablement will lead the formalization of AI enablement as a function at Crain Communications. They will embed with teams across the business to identify where AI can have the most impact, define policy and guardrails, educate the workforce, and drive adoption across the organization.

Responsibilities

• Bring a consultative approach to every engagement, taking the time to understand a team's workflows, challenges, and goals before identifying where AI can make a real difference.
• Partner with leaders across all major functions to surface workflow friction, knowledge gaps, and high-value opportunities where AI tools or training can make a meaningful difference.
• Own and drive the enterprise AI enablement roadmap, scoping, prioritizing, and executing a portfolio of initiatives from discovery through adoption and measurement.
• Define and maintain company-wide AI policy and guardrails, ensuring Crain is adopting AI in a way that is responsible, secure, and aligned with our values and obligations.
• Lead the effort to capture and centralize Crain's institutional knowledge (decisions, processes, data, and expertise) into AI-powered knowledge bases that make the whole organization smarter.
• Work with IT Services on the company-wide rollout of Claude Enterprise, driving adoption and ensuring teams are set up to get real value from the platform within our Microsoft 365 environment.
• Identify and implement agentic workflows and automation that reduce manual overhead across key business functions.
• Implement and manage a company-wide AI micro-learning platform, rolling it out in deliberate phases starting where it will have the most impact, tracking adoption and outcomes at each stage to learn, iterate, and expand intelligently across the organization.
• Stay close to advancements in the AI space, continuously evaluating new tools, models, and capabilities; find regular, structured ways to surface and communicate relevant opportunities to stakeholders across Crain so we're always making informed decisions about what to explore, pilot, or adopt.
• Maintain a clear focus on cost efficiency and ROI across all AI initiatives; every tool evaluated, every workflow built, and every platform adopted should be held to a standard of delivering measurable value for the business.

Requirements

A consultative mindset; you listen before you prescribe, ask the right questions, and earn trust by understanding people's work before trying to change it.

Hands-on experience implementing AI tools and workflows inside an organization; you've actually done this, not just theorized about it.

Deep familiarity with Claude and the Anthropic ecosystem, including how to get the most out of it in an enterprise context.

Practical experience designing and deploying agentic workflows; you understand how to connect systems, automate multi-step processes, and build solutions that run with minimal human intervention.

Proven ability to drive strategic initiatives, influence without authority, and earn trust across an organization.

Comfort working across technical and non-technical stakeholders; you can talk to engineers and align a department head in the same afternoon.

An understanding of how data flows through an organization and why connecting those flows matters.

A bias toward outcomes over outputs; you care whether it worked, not just whether it shipped.

Demonstrated track record leading digital transformation or AI adoption initiatives inside a mid-to-large organization.

Direct, hands-on experience with Claude, ideally Claude Enterprise, including deploying it across teams, building Projects and knowledge bases, and driving measurable adoption.

Experience designing and implementing agentic workflows that connect enterprise systems and reduce manual processes.

Background working cross-functionally at a senior level, translating organizational needs into AI-powered solutions that stick.

Familiarity with change management in the context of technology adoption; you know how to bring skeptics along and build lasting habits, not just launch tools.

Experience evaluating, piloting, and recommending AI tools and platforms in a business context.

Prior work in media, publishing, or a similarly complex multi-brand or multi-business-unit environment is a plus.

Skills

• Technical Claude and the Anthropic platform (Claude Enterprise, Projects, Cowork, Code, etc.)
• Agentic workflow design and implementation
• Experience working with SaaS integrations, APIs, and MCP connectors to connect enterprise systems and extend AI capabilities
• Prompt engineering and AI system design
• Deep understanding of data pipelines and how enterprise data sources connect

Benefits

Competitive benefits including retirement plan savings contributions and bonus opportunities based on individual and company performance.

Pay

The estimated salary range for this position is $140,000 to $160,000. The final salary offering will take into account a wide range of factors, including experience, accomplishments and location.

Schedule

This position is exempt under the Fair Labor Standards Act and is not eligible for overtime pay.

Location

Preferred location: Detroit. Also possible: Chicago or Manhattan offices. In office 3 days per week.