AI Transformation Lead

Pencil

1d•Remote

About The Position

At Pencil, the AI Transformation Lead is the strategic and technical owner of transformation engagements across a defined set of accounts. The role determines what Pencil should do for each client and how the work should be delivered, setting the transformation thesis and owning the recommendations and client narrative. The Lead structures engagements from first principles, co-designs recommendations and timelines with Forward Deployed Engineers and Creative Leads, guides clients through enterprise-wide change, and remains accountable for quality and performance after launch. The role also translates generative AI concepts into practical operating processes, shares customer insights with Product and Engineering, and documents successful approaches as repeatable Transformation Blueprints. Success is measured by enterprise adoption, time-to-value, the quality and performance of transformation plans, product feedback impact, and contribution to 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.
Uses AI tools in day-to-day work and already uses Claude Cowork.
Hands-on technical fluency, including the ability to work in the Pencil platform and discuss a client's technical stack with its engineers.
Confidence leading client meetings independently, giving direct feedback, and remaining 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 to clients.
Ability to challenge customers' existing ways of working and support technology adoption beyond pilot projects.
Lead with transparency, agility, and a focus on 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 the strategic and tactical plan for each engagement, including the transformation thesis and recommendations co-designed with Forward Deployed Engineers and Creative Leads.
Structure ambiguous client problems from first principles into hypotheses, workstreams, and sequenced decisions.
Lead clients through enterprise-wide transformation, moving them from siloed pilots to integrated AI-driven workflows; navigate stakeholders, identify blockers and champions, and build buy-in for scaled adoption.
Translate generative AI concepts into clear, repeatable operating processes that client teams can use day to day.
Represent the voice of the customer internally by sharing product insights with Product and Engineering.
Codify successful account approaches into repeatable Transformation Blueprints for the wider team.
Configure agents, prototype, and stress-test recommendations in the Pencil platform, and stand behind the quality and performance of shipped work.