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Pencil is an advertising technology SaaS company using Generative AI to redefine content creation. The company's mission is to democratize AI in advertising, making it accessible to small businesses and creative individuals, not just enterprise brands.
As AI Transformation Lead, you will be the strategic and technical owner of transformation engagements for a defined set of accounts. You will be the most informed voice on what Pencil should deliver to each client and how the work gets executed. Your core responsibilities include:
**Implementation Leadership**: Own the narrative and strategic/tactical plan for each engagement. Set the transformation thesis, co-design recommendations with Forward Deployed Engineers and Creative Leads, and drive the client through enterprise-wide change to ensure adoption sticks. You own both the recommendations and the story told to clients.
**Structured Problem-Solving**: Take ambiguous client problems and structure them from first principles into clear hypotheses, workstreams, and sequenced decisions that teams can act on.
**Change Management Leadership**: Lead clients through enterprise-wide transformation, moving them beyond siloed pilots into integrated, AI-driven workflows. Navigate complex stakeholder landscapes, identify blockers and champions, and engineer the buy-in required for scaled AI adoption.
**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 on what's missing, broken, or worth doubling down on, keeping Pencil's roadmap enterprise-ready.
**Transformation Blueprints**: Codify successful engagement patterns into repeatable Blueprints that the broader team can run, ensuring every win leaves behind a sharper playbook.
Success is measured by enterprise adoption depth/breadth, time-to-value, quality of transformation narrative, product feedback impact, and blueprint contribution.
**Requirements**:
- Strong academic record in a quantitative or analytical discipline (STEM, economics, engineering, or business) that taught you to break hard problems apart and defend reasoning under scrutiny
- Minimum 5 years' experience in consulting, in-house transformation, programme management, or enterprise tech implementation with exposure to technology, digital strategy, and/or operations
- AI-native in day-to-day work; already use Claude or similar tools; experience with Claude Code or other agentic tooling is a strong plus; proactive about automation
- Tech-fluent and hands-on; comfortable configuring agents, prototyping, stress-testing recommendations in the Pencil platform; can hold technical conversations with client engineers about their stack; lightweight engineering skills (SQL, scripts, reading code) are a strong plus
- Confident with senior stakeholders; can carry client meetings independently, give direct feedback, and stay composed when scope shifts
- Track record of delivering complex, cross-functional, often ambiguous work to high standard and on time
- Marketing, advertising, or agency experience is helpful but not a differentiator
