AI Transformation Lead

Pencil; Toronto (OH); Hybrid; USD 140,000 - 190,000; Full time

Job summary

Pencil is hiring a strategic and technical leader to own transformation engagements for a defined set of accounts. You will set the thesis, structure the engagement, co-design recommendations with engineers, and shepherd enterprise-wide change from pilots to scalable AI-enabled workflows.

You will ensure quality and performance post-delivery and own the client narrative. Candidates must be based in North America and have consulting and/or agency experience to be considered for this role.

Qualifications

• Minimum of 5 years’ experience in consulting or an agency setting, in-house transformation, programme management, or enterprise technology implementation.
• AI-native in your day-to-day. You already use Claude Cowork; experience with Claude Code or other agentic tooling is a strong plus.
• Tech-fluent and hands-on. You’re in the Pencil platform yourself - configuring agents, prototyping, stress-testing recommendations.
• Confident with senior stakeholders. You can carry a client meeting on your own 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.

Responsibilities

• Implementation Leadership: Own the narrative told to the client and the strategic and tactical plan that drives the engagement.
• Structured Problem-Solving: Structure ambiguous client problems from first principles into hypotheses and workstreams.
• Change Management Leadership: Lead enterprise-wide transformation and AI-driven workflows with stakeholder buy-in.
• AI Process Design: Translate GenAI concepts into repeatable operating processes.
• Product Feedback Loop: Act as the voice of the customer to inform product and engineering.
• Transformation Blueprints: Codify repeatable playbooks for future engagements.

Skills

Consulting experience

Agency experience

Change management

Strategic thinking

Client leadership

Education

Quantitative field degree

Tools

Claude Cowork

Claude Code

Agentic tooling

SQL

Scripting

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