AI Transformation Lead

Pencil; Toronto (OH); Remote; USD 120,000 - 180,000; Full time

Benefits offered by this job

25 days PTO

Health insurance

Wellness stipend

Remote work

Enhanced parental leave

Job summary

Pencil is transforming advertising technology with a Generative AI-powered SaaS product. We partner with clients to deliver enterprise-scale transformations, building AI-enabled workflows and repeatable playbooks that accelerate value while preserving human creativity.

As an AI-native consultant, you will lead engagements from discovery through implementation, engaging senior stakeholders, prototyping AI-driven solutions, and codifying best practices into pencil-wide blueprints for scalable

Qualifications

• Strong problem-solving ability with structured reasoning.
• Experience leading enterprise transformations or tech implementations.
• Proactive with automation and AI-enabled workflows.

Responsibilities

• Own the narrative and plan for client engagements across transformation initiatives.
• Structure ambiguous problems into hypotheses, workstreams, and decisions.
• Lead enterprise-wide change management and AI-driven workflows.
• Translate GenAI concepts into repeatable operating processes for client teams.
• Act as the voice of the customer to guide product and engineering feedback.
• Create repeatable Transformation Blueprints from account experiences.

Skills

Consulting

Transformation

Stakeholder mgmt

GenAI

SQL

Education

Bachelor's degree

Tools

Claude Cowork

Claude Code

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.

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:

• 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.
• Marketing, advertising, or agency experience helps, but it's not what sets candidates apart

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