AI Transformation Lead

Pencil

3d • Remote

About The Position

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. 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 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. You own the recommendations and the narrative we tell our clients.

Requirements

• 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 your reasoning under scrutiny.
• Minimum of 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 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.

Nice To Haves

• Marketing, advertising, or agency experience helps, but it’s not what sets candidates apart
• experience with Claude Code or other agentic tooling is a strong plus
• Lightweight engineering - SQL, scripts, reading code - is a strong plus.

Responsibilities

• 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
• Take ambiguous client problems and structure them from first principles into a clear set of hypotheses, workstreams, and sequenced decisions everyone can act on.
• 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.
• Translate abstract GenAI concepts into clear, repeatable operating processes that client teams can execute confidently day-to-day.
• 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.
• 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.

Benefits

• 25 days PTO plus public holidays, although we operate 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, whether you become a parent through birth, adoption or surrogacy
• Access to our Pencil office in The Shard, London for UK employees
• Flexible working hours

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed