Enterprise AI Transformation Leader

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

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.