AI Transformation Lead

Pencil • , CT

1d • Remote

About The Position

Pencil is hiring an AI Transformation Lead to own strategic and technical transformation engagements for a defined set of accounts. The role is the primary authority on what Pencil should do for each client and how the work should be delivered. The Lead 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 the quality and performance of recommendations after launch. The role owns both the recommendations and the client-facing narrative.

The AI Transformation Lead turns ambiguous client challenges into structured hypotheses, workstreams, and sequenced decisions; translates generative AI concepts into repeatable operating processes; and helps clients progress from siloed pilots to integrated, AI-driven workflows. The role also represents customer needs to Product and Engineering and develops reusable Transformation Blueprints from successful engagements.

Candidates must be based in North America and have consulting and/or agency experience. Marketing, advertising, or agency experience is essential. Success is measured by enterprise adoption, time-to-value, quality of the transformation narrative, product feedback impact, and contributions to reusable blueprints.

Requirements

• At least 5 years of experience in consulting or an agency setting, in-house transformation, programme management, or enterprise technology implementation.
• Exposure to technology, digital strategy, and/or operations.
• Marketing, advertising, or agency experience; this is stated as essential.
• Must be based in North America.
• Day-to-day use of AI tools, including Claude Cowork, and a proactive approach to automation.
• Technical fluency and hands-on capability, including the ability to configure agents, prototype, stress-test recommendations, and discuss a client's technology stack with engineers.
• Confidence engaging with senior stakeholders, independently leading client meetings, giving direct feedback, and remaining composed when scope changes.
• A track record of delivering complex, cross-functional, often ambiguous work to a high standard and on time.
• Comfort with ambiguity and change, and the ability to act as a trustworthy partner through unfamiliar situations.
• Willingness to challenge clients' existing ways of working when needed to prevent long-term implementation challenges.
• Commitment to enterprise adoption and embedding technology into company workflows and culture.

Nice To Haves

• A 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-facing 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 actionable hypotheses, workstreams, and sequenced decisions.
• Lead clients through enterprise-wide transformation, moving them from siloed pilots toward integrated, AI-driven workflows; navigate stakeholders, identify 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 voice of the customer internally by sharing insights with Product and Engineering about product gaps, issues, and opportunities.
• Create repeatable Transformation Blueprints from successful engagements for use by the wider team.
• Configure agents, prototype, and stress-test recommendations in the Pencil platform.
• Stand behind the quality and performance of recommendations once the work ships.

Benefits

• 25 days of PTO plus public holidays, under a Flexible Time Off scheme.
• Health insurance or 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 policies for parents 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