AI Transformation Lead

Pencil • Virginia, MN

2d • 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, structuring engagements from first principles, co-designing recommendations and timelines with Forward Deployed Engineers and Creative Leads, and leading clients through enterprise-wide change. The role owns client recommendations and narratives, and remains accountable for quality and performance after launch.

The position focuses on helping clients move beyond siloed pilots toward integrated, AI-driven workflows and sustained enterprise adoption. It translates generative AI concepts into repeatable operating processes, serves as the customer voice internally to Product and Engineering, and documents successful approaches as reusable Transformation Blueprints.

Candidates must be based in North America and have consulting and/or agency experience. Marketing, advertising, or agency experience is essential.

Requirements

• Minimum of 5 years’ experience in consulting or an agency setting, in-house transformation, programme management, or enterprise technology implementation, with exposure to technology, digital strategy, and/or operations.
• Marketing, advertising, or agency experience is essential.
• Must be based in North America.
• Uses Claude Cowork in day-to-day work and is proactive about automation.
• Technically fluent and hands-on, including the ability to configure agents, prototype, and stress-test recommendations in Pencil.
• Able to hold a technical conversation with client engineers about their technology stack.
• Confident managing senior-stakeholder meetings, 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.
• Comfortable with ambiguity and change, and able to challenge existing client practices constructively.

Nice To Haves

• Strong academic record in a quantitative or analytical discipline.
• Experience with Claude Code or other agentic tooling.
• Lightweight engineering skills such as SQL, scripting, or reading code.

Responsibilities

• Own the client narrative and the strategic and tactical plan for each engagement, including setting the transformation thesis and co-designing 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 transformation, navigating stakeholders, identifying blockers and champions, and building support for scaled AI adoption.
• Translate generative AI concepts into clear, repeatable operating processes for client teams.
• Feed customer insights to Product and Engineering to help guide Pencil’s roadmap and address product gaps or opportunities.
• Document successful engagement approaches as repeatable Transformation Blueprints for use by the wider team.
• Configure agents, prototype, and stress-test recommendations in the Pencil platform.
• Deliver complex, cross-functional work to a high standard and on time.
• Track and contribute to enterprise adoption, time-to-value, transformation narrative quality, product feedback impact, and Blueprint contribution.

Benefits

• 25 days PTO plus public holidays, with a Flexible Time Off scheme.
• Health insurance / private medical cover.
• Monthly stipend toward 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 the Pencil 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