Director, Enterprise AI Enablement

Description

Crain Communications is already well into its AI journey. We've built our own RAG-based product for customers, developed internal AI tools across multiple departments, and have people throughout the business building new things every day. AI is not new here; it's already woven into how we work.

What we need now is intentionality. Things are moving fast and the opportunity is real, but to scale this across the whole company we need to formalize AI enablement as a function, move from individual experimentation in silos to cohesive, structured execution, and ensure we're doing this with clear guardrails, consistent processes, and a deliberate strategy for where we go next.

The goal is bigger than efficiency gains. We're building toward a version of Crain that actually understands itself, where decisions, knowledge, workflows, and institutional memory are captured, connected, and made continuously available to inform how we work and where we're headed.

That's what this role is. The Director, Enterprise AI Enablement will approach this work with a consultative mindset, embedding with teams across the business to understand their world before prescribing solutions. They will own identifying where AI can have the most impact by engaging directly with people throughout the business and distilling that into clear opportunities; setting the policy and guardrails that ensure we're adopting AI in a safe and thoughtful way;

and educating the workforce and driving real, lasting adoption across the whole company. This role will have at least one direct report from the start, with the expectation that the team will grow as the function matures.

You'll work across Editorial, Sales, Marketing, HR, Finance, Technology, and Product to find where knowledge is siloed, where decisions are slowed by friction, and where the right AI tooling can unlock real capability. Then you'll build it, sometimes hands-on, sometimes by working through and alongside the teams closest to the problem.

Key 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

What you'll bring:

* 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,…