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AI Transformation Lead

Pencil
Connecticut, USA
Full-time
Lead
Remote
Discovered 3 days ago

Full Job Posting

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, 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, 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 - 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.
  • Your background:
  • 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.
  • You’ll Thrive Here If You...
  • 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.
  • Embody 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.
  • KPIs & Success Measures
  • Enterprise Adoption: Depth and breadth of Pencil usage across a customer's teams, departments, and use cases once the rollout is live.
  • Time-to-Value: Speed at which your accounts reach their first defined success metric or ROI milestone after engagement kickoff.
  • Quality of Transformation Narrative: How well your transformation thesis and the strategic and tactical planning survive delivery without major rework, and the performance the recommendation drives for the client post-launch.
  • Product Feedback Impact: Quality and reach of insights fed back to Product and Engineering that keep Pencil's roadmap enterprise-ready.
  • Blueprint Contribution: Successful documentation and internal adoption of repeatable "Transformation Blueprints" based on customer wins.

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

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