Sr. Director, AI Enablement

The Senior Director, AI Enablement leads Caliber's AI Enablement team — the function responsible for turning AI investment into measurable business outcomes. This role is the face of AI inside Caliber: evangelizing possibilities, building and activating the super-user network across business functions, guiding business partners to the right tools for the right problems, capturing business cases for new AI initiatives, and measuring and reporting value delivery after implementation. This role requires equal parts technical credibility, business acumen, and people skills. The Senior Director, AI Enablement does not build AI systems — they ensure the humans at Caliber can use them effectively. 

KEY RESPONSIBILITIES 

▸  AI Enablement Strategy & Roadmap — Define and execute the AI enablement roadmap; prioritize initiatives by business value and readiness; report progress to the CTO and ELT 

▸  Super-User Network — Build, train, and sustain a network of embedded AI super-users within each major business function (Estimating, Parts, Field Ops, Finance, HR, DRP/Insurance) 

▸  Business Partner Engagement — Partner with functional leaders to explore the art of the possible; translate operational pain points into AI opportunity assessments 

▸  Tool Guidance & Routing — Guide business partners to the right AI tool for each problem — preventing misuse, mismatched expectations, and shadow adoption 

▸  Business Case Development — Work with business partners to frame and document AI use case business cases using Caliber's standard charter and CBA templates 

▸  Value Realization — Track and report realized value after AI deployments; own the AI value register that demonstrates Transformation ROI to leadership 

▸  Training & Content — Develop and deliver AI training programs for all teammate levels — from executive awareness to practitioner-level usage 

▸  Best Practice Enforcement — Maintain and communicate AI usage best practices in partnership with EA; identify and remediate misuse patterns 

▸  AI Governance Forum — Co-lead the AI Governance Forum with the Head of EA & AI Platforms; triage new use cases and surface policy questions to leadership 

WHAT SUCCESS LOOKS LIKE 

▸  Year 1 — Super-user network active in 5+ business functions; AI training program launched; first cohort of use cases with documented business cases and value capture in flight 

▸  Year 2 — AI value register demonstrates measurable EBITDA or efficiency impact; Transformation is self-sustaining with clear demand pipeline; internal AI literacy materially elevated 

REQUIRED QUALIFICATIONS 

▸  8+ years in technology, management consulting, or a change management / program management function 

▸  Direct experience with AI tools in a business context — not just awareness, but hands-on usage and training delivery 

▸  Demonstrated ability to build coalitions and drive adoption across a large, geographically distributed organization 

▸  Experience developing business cases, ROI models, and value measurement frameworks 

▸  Excellent executive communication skills — comfortable presenting to the CTO, COO, CEO, and CFO 

▸  Strong program management discipline; able to run multiple concurrent initiatives without dropping threads 

PREFERRED QUALIFICATIONS 

▸  Experience building or leading an AI, digital, or technology Transformation function, or equivalent experience consulting to organizations in transformation 

▸  Familiarity with Claude Enterprise, Microsoft 365 Copilot, or Moveworks from an end-user or enablement perspective 

▸  Background in process improvement for corporate functions 

▸  Background in collision repair, insurance, auto, or operationally intensive industries, optional 

▸  Experience as a business partner