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. 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 the recommendations and timelines with Forward Deployed Engineers and Creative Leads, lead the client through the enterprise-wide change required to make it stick, and stand behind quality and performance once the work ships.

Responsibilities

Own the narrative told to the client and the strategic and tactical plan that drives the engagement; Set the transformation thesis and co-design recommendations with Forward Deployed Engineers and Creative Leads; Take ambiguous client problems and structure them from first principles into hypotheses, workstreams, and sequenced decisions; Lead clients through enterprise-wide transformation, moving them beyond siloed pilots into integrated, AI-driven workflows; Identify blockers and champions and engineer buy-in for scaled AI adoption; Translate abstract GenAI concepts into clear, repeatable operating processes; Act as the voice of the customer internally, feeding insights back to Product and Engineering; Codify successful engagements into repeatable Transformation Blueprints

Requirements

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; AI-native in day-to-day work, using Claude Cowork; Tech-fluent and hands-on, working in the Pencil platform (configuring agents, prototyping, stress-testing recommendations); Ability to hold a technical conversation with a client's engineers about their stack; Confident with senior stakeholders, able to carry a client meeting independently, give direct feedback, and stay composed when scope shifts; Track record of delivering complex, cross-functional, often ambiguous work to a high standard and on time; Marketing, advertising, or agency experience is essential; Candidates must be based in North America and have consulting and/or agency experience

Nice to have

Experience with Claude Code or other agentic tooling; Lightweight engineering skills such as SQL, scripts, and reading code; Provocative and brave, willing to challenge a customer's existing way of working; Ally to change, comfortable with ambiguity; Believes in enterprise adoption and moving technology beyond pilot purgatory

Benefits

25 days PTO plus public holidays, with a Flexible Time Off scheme; Health insurance / private medical cover; Monthly stipend towards wellness, fitness, and learning and development; Remote 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