AI Transformation Lead

Pencil • Atlanta, GA

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 the work should be delivered, establishes the transformation thesis, 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 owns both the recommendations and the client-facing narrative.

The position translates ambiguous client challenges and abstract generative AI concepts into actionable hypotheses, sequenced workstreams, and repeatable operating processes. It leads clients from siloed pilots toward integrated, AI-driven workflows by navigating stakeholder groups, identifying blockers and champions, and building support for scaled adoption. Internally, it represents the customer to Product and Engineering and turns successful account work into reusable Transformation Blueprints.

Success is measured by enterprise adoption, time-to-value, the quality and effectiveness of transformation recommendations, the impact of product feedback, and the documentation and internal adoption of repeatable blueprints. Pencil describes its mission as making AI the default in advertising without replacing creative people, while extending its technology beyond big brands to small businesses and creative individuals.

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.
• Technical fluency and hands-on ability to work in the Pencil platform, configure agents, prototype, and discuss a client's technology stack with engineers.
• Confidence working with senior stakeholders, 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 during transformation.

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 transformation engagements.
• Set the transformation thesis and co-design recommendations 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 change, helping move them from siloed pilots to integrated, AI-driven workflows.
• Navigate stakeholder landscapes, identify blockers and champions, and build buy-in for scaled AI adoption.
• Translate generative AI concepts into clear, repeatable operating processes for client teams.
• Represent the voice of the customer internally by sharing product insights with Product and Engineering.
• Codify successful account approaches into repeatable Transformation Blueprints.
• Configure agents, prototype, and stress-test recommendations in the Pencil platform.
• Stand behind the quality and performance of work after it ships.

Benefits

• 25 days of PTO plus public holidays, with a Flexible Time Off scheme.
• Health insurance / private medical cover.
• Monthly stipend for wellness, fitness, and learning and development.
• Remote work from anywhere in the employee's home country.
• Enhanced parental leave for becoming a parent through birth, adoption, or surrogacy.
• Access to Pencil's office in The Shard, London for UK employees.
• Flexible working hours.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed