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 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 set the thesis, structure the engagement from first principles, co-design recommendations and timelines with Forward Deployed Engineers and Creative Leads, lead clients through required enterprise-wide change, and stand behind quality and performance post-launch.

Key Responsibilities

• Implementation Leadership: Own the narrative told to the client and the strategic and tactical plan driving the engagement. Set the transformation thesis and co-design 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.
• Change Management Leadership: Lead clients through enterprise-wide transformation beyond siloed pilots into integrated, AI-driven workflows by navigating complex stakeholder landscapes.
• 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 actionable insights back to Product and Engineering to keep Pencil's roadmap enterprise-ready.
• Transformation Blueprints: Codify successful account engagements into repeatable playbooks for internal scaling.

Your Background

• Strong academic record in a quantitative or analytical discipline (STEM, economics, engineering, or business).
• Minimum 5 years of experience in consulting, in-house transformation, program management, or enterprise tech implementation with exposure to technology, digital strategy, or operations.
• AI-native mindset with hands-on experience using tools like Claude Cowork, Claude Code, or other agentic tooling.
• Tech-fluent and hands-on, with experience configuring agents, prototyping, and holding technical conversations with client engineers. Lightweight engineering skills (SQL, scripts, reading code) are a strong plus.
• Confident managing senior stakeholders, giving direct feedback, and staying composed when scope shifts.
• Proven track record of delivering complex, cross-functional, and ambiguous work to a high standard and on time.
• Marketing, advertising, or agency experience is beneficial, but not required.

You’ll Thrive Here If You...

• Are Provocative and Brave: Challenge a customer's existing way of working to help them avoid long-term implementation challenges.
• Are an Ally to Change: Are comfortable with ambiguity and take pride in guiding teams through the unknown.
• Believe in Enterprise Adoption: Are focused on moving technology past "pilot purgatory" into an embedded, value-driving core of business success.
• Embody Pencil Values: Lead with transparency, agility, and a focus on measurable impact.

KPIs & Success Measures

• Enterprise Adoption: Depth and breadth of Pencil usage across customer teams, departments, and use cases once live.
• Time-to-Value: Speed at which accounts reach their first defined success metric or ROI milestone.
• Quality of Transformation Narrative: Integrity and resilience of strategic frameworks through execution and post-launch client performance.
• Product Feedback Impact: Quality and reach of insights fed back to Product and Engineering.
• Blueprint Contribution: Documentation and internal adoption of repeatable Transformation Blueprints based on wins.

Benefits

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