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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 large 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 driving each engagement. Set the transformation thesis, co-design recommendations with Forward Deployed Engineers and Creative Leads, and ensure quality and performance post-launch.
**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.
**Transformation Blueprints**: Codify successful engagement patterns into repeatable Blueprints that the broader team can run, ensuring each win leaves behind a sharper playbook.
You will be measured on enterprise adoption depth/breadth, time-to-value, quality of transformation narrative, product feedback impact, and blueprint contribution.
**Requirements**:
- Minimum 5 years' experience in consulting, agency, in-house transformation, programme management, or enterprise technology implementation, with exposure to technology, digital strategy, and/or operations
- Strong academic record in a quantitative or analytical discipline preferred
- AI-native in day-to-day work; already use Claude or similar agentic tooling; proactive about automation
- Tech-fluent and hands-on; comfortable configuring agents, prototyping, stress-testing recommendations, and holding technical conversations with client engineers
- 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 during scope shifts
- Track record of delivering complex, cross-functional, ambiguous work to high standard and on time
- Marketing, advertising, or agency experience is essential
- Must be based in North America
