Director, Enterprise AI Enablement

Role Overview

• 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

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

Tech Stack

• AWS

Benefits

• competitive benefits including retirement plan savings contributions and bonus opportunities based on individual and company performance