AI Transformation Lead

Pencil

. Own the strategic and technical direction of transformation engagements for assigned accounts .

Posted 10/23/2026full-timeRemote • Connecticut • United StatesSeniorWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading enterprise-wide transformation engagements, with a strong focus on AI adoption and digital strategy. Proficient in translating complex concepts into actionable processes while effectively navigating stakeholder landscapes and delivering high-quality recommendations.

Highest-signal resume keywords

Enterprise Technology ImplementationAI AdoptionTransformation StrategyClient EngagementCross-Functional Project Management

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

SQLPrototypingStress TestingConfiguration of AgentsTransformation Blueprint Development

Soft Skills

Stakeholder ManagementCommunicationAnalytical ThinkingProblem SolvingLeadership

Tools & Technologies

Claude CoworkClaude CodePencil Platform

Industry Keywords

ConsultingDigital StrategyMarketingAdvertisingProgramme Management

Tech Stack

Tools & technologies

SQL

About the role

Key responsibilities & impact

Own the strategic and technical direction of transformation engagements for assigned accounts
Set the transformation thesis and structure engagements from first principles
Co-design recommendations and timelines with Forward Deployed Engineers and Creative Leads
Lead clients through enterprise-wide change and AI adoption
Navigate stakeholder landscapes, identify blockers and champions, and build buy-in
Translate generative AI concepts into repeatable operating processes
Act as the internal voice of the customer for Product and Engineering feedback
Codify successful account approaches into repeatable Transformation Blueprints
Own client recommendations and transformation narratives
Track enterprise adoption, time-to-value, transformation narrative quality, product feedback impact, and Blueprint contribution

Requirements

What you’ll need

Candidates must be based in North America
Minimum of 5 years’ 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 is essential
Strong academic record in a quantitative or analytical discipline is preferred
AI-native in day-to-day work; already use Claude Cowork
Experience with Claude Code or other agentic tooling is a strong plus
Tech-fluent and hands-on; able to configure agents, prototype, and stress-test recommendations in the Pencil platform
Able to hold a technical conversation with client engineers about their stack
Lightweight engineering skills such as SQL, scripts, and reading code are a strong plus
Able to independently carry client meetings and give direct feedback
Track record of delivering complex, cross-functional, ambiguous work to a high standard and on time

Benefits

Comp & perks

25 days PTO plus public holidays, although we operate a Flexible Time Off scheme
Health insurance / private medical cover
Monthly stipend towards wellness, fitness, and learning and development
Remote - work from anywhere in your home country
Enhanced parental leave policies, whether you become a parent through birth, adoption or surrogacy
Access to our Pencil office in The Shard, London for UK employees
Flexible working hours