AI Transformation Lead

Pencil

. Own the narrative told to the client and the strategic and tactical plan driving each engagement .

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

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading enterprise-wide transformations and AI-driven workflows, with a strong focus on client engagement and strategic planning. Proficient in translating complex AI concepts into actionable processes while maintaining high standards of quality and performance.

Highest-signal resume keywords

Enterprise-Wide TransformationAI-Driven WorkflowsConsulting ExperienceClient EngagementTechnical Conversation Skills

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

SQLScriptingReading CodePrototypingStress-Testing Recommendations

Soft Skills

LeadershipCommunicationProblem-SolvingStakeholder Management

Tools & Technologies

Claude CoworkClaude CodePencil Platform

Industry Keywords

Digital StrategyOperationsMarketingAdvertisingAgency Experience

Tech Stack

Tools & technologies

SQL

About the role

Key responsibilities & impact

Own the narrative told to the client and the strategic and tactical plan driving each engagement
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 transformation and 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
Act as the customer voice internally, feeding product insights to Product and Engineering
Codify successful account work into repeatable Transformation Blueprints
Stand behind quality and performance after work ships
Drive 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
Consulting and/or agency experience required
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
AI-native in day-to-day work; use of Claude Cowork
Experience with Claude Code or other agentic tooling is a strong plus
Hands-on experience configuring agents, prototyping, and stress-testing recommendations in the Pencil platform
Ability to hold a technical conversation with client engineers about their stack
Lightweight engineering skills such as SQL, scripting, and reading code are a strong plus
Ability to independently lead client meetings and give direct feedback
Track record of delivering complex, cross-functional, ambiguous work to a high standard and on time
Strong academic record in a quantitative or analytical discipline is preferred

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