AI Transformation Lead

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.

Candidates must be based in North America and have consulting and/or agency experience to be considered for this role.

• Implementation Leadership:
  Own the narrative told to the client and the strategic and tactical plan that drives the engagement, setting the transformation thesis, co-designing the 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, work streams, and sequenced decisions everyone can act on.
• Change Management Leadership:
  Lead clients through enterprise-wide transformation, moving them beyond siloed pilots into integrated, AI-driven workflows - navigating complex stakeholder landscapes, identifying blockers and champions, and engineering the buy-in that scaled AI adoption requires.
• 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 - what's missing, what's broken, what's worth doubling down on - so Pencil's roadmap stays enterprise-ready.
• Transformation Blueprints:
  Codify what works on your accounts into repeatable Blueprints the rest of the team can run, so every successful engagement leaves behind a sharper playbook than the one before it.

• Minimum of 5 years' experience in consulting or an agency setting, in-house transformation, programme management, or enterprise technology implementation, with exposure to technology, digital strategy, and/or operations. A strong academic record in a quantitative or analytical discipline is preferred.
• AI-native in your day-to-day. You already use Claude Cowork; experience with Claude Code or other agentic tooling is a strong plus. You don't wait to be told to automate something.
• Tech-fluent and hands-on. You're in the Pencil platform yourself - configuring agents, prototyping, stress-testing recommendations - and you can hold your own in a technical conversation with a client's engineers about their stack. Lightweight engineering - SQL, scripts, reading code - is a strong plus.
• Confident with senior stakeholders. You can carry a client meeting on your own, give direct feedback, and stay composed when scope shifts.
• A track record of delivering complex, cross-functional, often ambiguous work to a high standard and on time.
• Marketing, advertising, or agency experience is essential for this role.

• Are Provocative and Brave:
  You aren't afraid to challenge a customer's existing way of working if it means helping them avoid long-term implementation challenges.
• Are an Ally to Change:
  You are comfortable with ambiguity and change, and you take pride in being a trustworthy partner who helps others navigate the "new and unknown".
• Believe in Enterprise Adoption:
  You are obsessed with seeing technology move away from "pilot purgatory" and towards an embedded, value-driving part of a company's culture and success.
• Embode Pencil Values:
  You lead with transparency, agility, and a focus on measurable impact, ensuring our values are mirrored in the customer's own transformation journey.

• Enterprise Adoption:
  Depth…