AI Transformation Lead - Pencil

At Pencil, we are driving innovation in advertising technology through our state-of-the-art SaaS product, which harnesses Generative AI to redefine content creation. Our mission is to make AI the default in advertising without replacing creative people. To achieve this, we need to make sure that our technology isn’t just in the hands of big brands — we need to try to help small businesses and creative individuals too.

You will be the strategic and technical owner of transformation engagements on a defined set of accounts, acting as the most informed voice on what Pencil should do for each client and how the work gets done. You set the thesis, structure the engagement from first principles, co-design recommendations and timelines with Forward Deployed Engineers and Creative Leads, lead clients through enterprise-wide change, and stand behind quality and performance once the work ships.

Key Responsibilities

• Implementation Leadership: Own the narrative told to the client and the strategic and tactical plan that drives the engagement, setting the transformation thesis and co-designing recommendations with Forward Deployed Engineers and Creative Leads.
• Structured Problem-Solving: Take ambiguous client problems and structure them from first principles into a clear set of hypotheses, workstreams, and sequenced decisions everyone can act on.
• Change Management Leadership: Lead clients through enterprise-wide transformation beyond siloed pilots into integrated, AI-driven workflows — navigating complex stakeholder landscapes, identifying blockers and champions, and engineering buy-in.
• AI Process Design: Translate abstract GenAI concepts into clear, repeatable operating processes that client teams can execute confidently day-to-day.
• Product Feedback Loop: Act as the voice of the customer internally, feeding insights back to Product and Engineering to ensure Pencil's roadmap stays enterprise-ready.
• Transformation Blueprints: Codify successful account strategies into repeatable Blueprints for the team to use across future engagements.

Your Background

• A strong academic record in a quantitative or analytical discipline (STEM, economics, engineering, or business) demonstrating rigorous problem-solving and reasoning skills.
• Minimum of 5 years of experience in consulting, in-house transformation, programme management, or enterprise tech implementation with exposure to technology, digital strategy, and/or operations.
• AI-native in your day-to-day workflows (e.g., active user of Claude Cowork; experience with Claude Code or agentic tooling is a strong plus).
• Tech-fluent and hands-on, capable of configuring agents, prototyping, and holding technical conversations with client engineers. Lightweight engineering skills (SQL, scripting, reading code) are a plus.
• Confident managing senior stakeholders, leading client meetings independently, delivering direct feedback, and adapting when scope shifts.
• Proven track record of delivering complex, cross-functional, and ambiguous projects on time to a high standard.
• Experience in marketing, advertising, or agency environments is helpful but not required.

You'll Thrive Here If You...

• Are Provocative and Brave: Challenge customer status quos to help them avoid long-term implementation pitfalls.
• Are an Ally to Change: Navigate ambiguity with confidence and guide partners through the unknown.
• Believe in Enterprise Adoption: Are driven to move technology past "pilot purgatory" and into embedded daily value.
• Embody Pencil Values: Lead with transparency, agility, and a focus on measurable impact.

KPIs & Success Measures

• Enterprise Adoption: Depth and breadth of Pencil usage across client teams, departments, and use cases.
• Time-to-Value: Speed at which accounts reach their first defined success metric or ROI milestone.
• Quality of Transformation Narrative: How effectively the strategic transformation thesis survives delivery and drives client performance post-launch.
• Product Feedback Impact: Quality and reach of insights delivered to Product and Engineering teams.
• Blueprint Contribution: Documentation and adoption of repeatable "Transformation Blueprints."

Benefits

• 25 days PTO plus public holidays (with flexible time off options)
• Health insurance / private medical cover
• Monthly stipend towards wellness, fitness, and learning & development
• Remote working from anywhere in your home country
• Enhanced parental leave policies (birth, adoption, surrogacy)
• Access to the Pencil office in The Shard, London (for UK employees)
• Flexible working hours