Director, Enterprise AI Enablement

Crain Communications•Detroit, MI

1d•$140,000 - $160,000•Hybrid

About The Position

Crain Communications is seeking a Director, Enterprise AI Enablement to formalize and scale AI enablement as a function within the company. This role will move the company from individual experimentation to cohesive, structured execution with clear guardrails, consistent processes, and a deliberate strategy. The goal is to build a version of Crain that understands itself, where decisions, knowledge, workflows, and institutional memory are captured, connected, and made continuously available. The Director will approach this work with a consultative mindset, embedding with teams to understand their world before prescribing solutions. They will identify AI's impact, set policy and guardrails, and educate the workforce to drive adoption. This role will initially have at least one direct report, with expectations of team growth. The Director will collaborate across Editorial, Sales, Marketing, HR, Finance, Technology, and Product to identify opportunities for AI to unlock capabilities, building solutions sometimes hands-on and sometimes alongside teams closest to the problem.

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
Strong instincts for discovery; you know how to ask the right questions and turn ambiguous problems into clear, scoped work
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
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
Soft skills Consultative mindset; you listen to understand before moving to solutions
Executive-level stakeholder management and communication
Ability to translate ambiguity into structured, actionable plans
Curiosity and a habit of continuous learning
Comfort with change and the ability to bring others along through it
Collaborative by default, decisive when it matters

Nice To Haves

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

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: HR resources, customer research, sales and marketing materials, process documentation, and more
Partner 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
Build a structured approach to connecting Crain's core data sources (Naviga, Salesforce, ArcXP, Smartsheet, Fireflies, AWS, and others) as inputs into a coherent, AI-accessible model of how the business operates
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