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. You will be 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 the client through enterprise-wide change required to make it stick, 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, 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 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, leaving behind a sharper playbook for future engagements.

Your Background

• A 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 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 workflow, using agentic tooling (experience with Claude Cowork, Claude Code, etc. is a strong plus).
• Tech-fluent and hands-on: comfortable configuring agents, prototyping, stress-testing recommendations, and engaging in technical discussions with client engineers (lightweight engineering like SQL, scripting, reading code is a plus).
• Confident with senior stakeholders, capable of leading executive meetings solo, providing direct feedback, and maintaining composure when scope shifts.
• Proven track record of delivering complex, cross-functional, and ambiguous initiatives to a high standard and on schedule.
• Marketing, advertising, or agency experience is helpful, though not required.

You'll Thrive Here If You

• Are Provocative and Brave: You challenge existing ways of working to help clients avoid long-term implementation pitfalls.
• Are an Ally to Change: You embrace ambiguity and act as a reliable partner guiding teams through the new and unknown.
• Believe in Enterprise Adoption: You are passionate about moving technology past "pilot purgatory" into embedded, value-driving operations.
• Embody Pencil Values: You lead with transparency, agility, and measurable impact.

KPIs & Success Measures

• Enterprise Adoption: Depth and breadth of Pencil usage across customer teams and workflows post-rollout.
• Time-to-Value: Speed at which accounts achieve initial success metrics or ROI milestones post-kickoff.
• Quality of Transformation Narrative: Strategic thesis and plan execution fidelity with high-performing client outcomes.
• Product Feedback Impact: Reach and actionable quality of insights shared with Product and Engineering.
• Blueprint Contribution: Documentation and internal adoption of repeatable Transformation Blueprints.

Benefits

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