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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 enterprises.
As AI Transformation Lead, you will be the strategic and technical owner of transformation engagements for a defined set of client accounts. You will set the transformation thesis, structure engagements from first principles, co-design recommendations with Forward Deployed Engineers and Creative Leads, lead clients through enterprise-wide change management, and own the quality and performance of delivered work.
Key Responsibilities:
- Own the strategic narrative and tactical plan for each client engagement, setting the transformation thesis and co-designing recommendations
- Take ambiguous client problems and structure them into clear hypotheses, workstreams, and sequenced decisions
- Lead clients through enterprise-wide AI transformation, moving beyond siloed pilots into integrated workflows; navigate complex stakeholder landscapes and engineer buy-in for scaled adoption
- Translate abstract GenAI concepts into clear, repeatable operating processes clients can execute confidently
- Act as the voice of the customer internally, feeding product insights back to Product and Engineering to keep the roadmap enterprise-ready
- Codify successful engagement patterns into repeatable Transformation Blueprints for team-wide adoption
Success is measured by enterprise adoption depth/breadth, time-to-value, quality of transformation narrative delivery, product feedback impact, and Blueprint contribution.
Requirements:
- Strong academic record in a quantitative or analytical discipline (STEM, economics, engineering, or business)
- 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 agentic tooling; proactive about automation
- Tech-fluent and hands-on; comfortable configuring AI agents, prototyping, stress-testing recommendations, and holding technical conversations with client engineers; SQL, scripting, or code-reading ability is a strong plus
- Confident with senior stakeholders; can lead 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 helpful but not required
