AI Transformation Lead

Pencil•Toronto, OH

1d•Remote

About The Position

At Pencil, the AI Transformation Lead is the strategic and technical owner of transformation engagements for a defined set of accounts. The role determines what Pencil should do for each client and how to deliver the work, setting the transformation thesis, structuring engagements from first principles, co-designing recommendations and timelines with Forward Deployed Engineers and Creative Leads, leading enterprise-wide client change, and standing behind quality and performance after launch. The role owns both the recommendations and the narrative presented to clients. The position translates Generative AI concepts into practical, repeatable operating processes and helps clients move beyond isolated pilots toward integrated, AI-driven workflows. It also serves as an internal customer voice for Product and Engineering and turns successful engagement practices into reusable Transformation Blueprints. Success is measured by the breadth and depth of customer adoption, time to the first success metric or ROI milestone, the quality and delivery performance of transformation plans, the impact of product feedback, and the creation and adoption of reusable blueprints.

Requirements

Strong academic record in a quantitative or analytical discipline such as STEM, economics, engineering, or business.
At least 5 years of experience in consulting, in-house transformation, programme management, or enterprise technology implementation, with exposure to technology, digital strategy, and/or operations.
Use AI tools in day-to-day work; experience with Claude Cowork is specified.
Be technically fluent and hands-on, including the ability to configure agents, prototype, stress-test recommendations, and discuss a client's technology stack with engineers.
Confidently lead client meetings, give direct feedback, and remain composed when scope changes.
Track record of delivering complex, cross-functional, often ambiguous work to a high standard and on time.
Comfort with ambiguity and change, and ability to act as a trustworthy partner.
Willingness to challenge clients' existing ways of working when needed to avoid long-term implementation challenges.
Focus on enterprise adoption and embedding technology into company workflows and culture.
Lead with transparency, agility, and measurable impact.

Nice To Haves

Experience with Claude Code or other agentic tooling.
Lightweight engineering skills such as SQL, scripting, or reading code.
Marketing, advertising, or agency experience.

Responsibilities

Own the client-facing narrative and strategic and tactical engagement plan; set the transformation thesis and co-design recommendations with Forward Deployed Engineers and Creative Leads.
Structure ambiguous client problems into clear hypotheses, workstreams, and sequenced decisions.
Lead enterprise-wide client change, moving organizations from siloed pilots to integrated AI-driven workflows; identify stakeholders, blockers, and champions and build support for scaled adoption.
Translate Generative AI concepts into clear, repeatable operating processes that client teams can use day to day.
Represent the customer internally by sharing insights with Product and Engineering about missing or broken capabilities and opportunities for further investment.
Document successful practices as repeatable Transformation Blueprints for use across the team.
Configure agents, prototype solutions, and stress-test recommendations in the Pencil platform.
Stand behind the quality and performance of work after it ships.