AI Transformation Lead

Pencil; East Windsor Hill (CT); Remote; USD 130,000 - 170,000; Full time

Benefits offered by this job

25 days PTO plus public holidays

Health insurance / private medical

Monthly stipend towards wellness, L&D

Remote - work from anywhere in yourホーム

Enhanced parental leave policies

Office access in The Shard, London

Flexible working hours

Job summary

Pencil is seeking a Transformation Engagement Lead to own strategic and technical transformations for defined client accounts across North America. You will shape the transformation thesis, work with Forward Deployed Engineers and Creative Leads, and drive enterprise-wide adoption of AI-powered workflows.

You’ll work with senior stakeholders, design repeatable blueprints, and ensure delivery excellence across cross-functional teams in a fast-paced SaaS environment.

Qualifications

• Minimum of 5 years’ experience in consulting or an agency setting, in-house transformation, programme management, or enterprise technology implementation.
• A strong academic record in a quantitative or analytical discipline is preferred.
• AI-native in day-to-day work; experience with Claude Code or other agentic tooling is a strong plus.
• Tech-fluent and hands-on; comfortable with Pencil platform and technical conversations with client engineers.
• Confident with senior stakeholders and able to carry client meetings independently.
• A track record of delivering complex, cross-functional work to a high standard and on time.
• Marketing, advertising, or agency experience is essential for this role.

Responsibilities

• Implementation Leadership: own the client narrative and the strategic/tactical plan driving the engagement.
• Structured Problem-Solving: convert ambiguous problems into hypotheses, workstreams, and decisions.
• Change Management Leadership: guide enterprise-wide transformation and AI adoption.
• AI Process Design: translate GenAI concepts into repeatable operating processes.
• Product Feedback Loop: relay customer insights to Product and Engineering for roadmap alignment.
• Transformation Blueprints: codify successful approaches into repeatable playbooks.

Skills

Consulting experience

AI-native

Tech fluency

Stakeholder management

Cross-functional delivery

Agency/Marketing experience

Education

Bachelor's degree in a quantitative discipline

Tools

Claude Cowork

Claude Code

SQL

Job description

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.

Candidates must be based in North America and have consulting and/or agency experience to be considered for this role.

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