Remote AI Transformation Lead

trypencil.com; Virginia; Remote; USD 150,000 - 210,000; Full time

Benefits offered by this job

PTO + holidays

Health insurance

Wellness stipend

Remote work

Parental leave

The Shard London office access

Flexible working hours

Job summary

Pencil is seeking a senior transformation leader to drive enterprise AI adoption and engagement strategy for client accounts. You will shape the thesis, co-design recommendations with engineers and creatives, and guide the transformation from pilots to scalable, AI-driven workflows.

The role blends strategy, technology, and client leadership across complex environments. You’ll work with senior clients, own delivery quality, and feed insights back to product teams to ensure an enterprise-ready

Qualifications

• Minimum 5 years in consulting or agency settings with transformation exposure.
• AI-native approach; experience with Claude Code or similar tooling is a plus.
• Hands-on tech fluency; ability to discuss client stacks with engineers.
• Comfort presenting to senior stakeholders and guiding scope changes.
• Track record delivering complex, cross-functional work on time.
• Marketing/advertising experience is essential.

Responsibilities

• Own the transformation thesis and engagement plan with clients and engineers.
• Structure problems from first principles into actionable workstreams.
• Lead enterprise-wide change and AI-driven workflows beyond pilots.
• Translate AI concepts into repeatable operating processes.
• Feed customer insights back to Product and Engineering for enterprise readiness.
• Codify successful approaches into repeatable Transformation Blueprints.

Skills

Consulting/agency experience

AI tooling (Claude Cowork)

Technical fluency (SQL, scripts)

Senior stakeholder management

Delivery of complex programs

Marketing/advertising experience

Education

Quantitative/analytical discipline

Tools

Claude Cowork

Claude Code

Agentic tooling

Job description

Pencil is seeking a senior transformation leader to drive enterprise AI adoption and engagement strategy for client accounts. You will shape the thesis, co-design recommendations with engineers and creatives, and guide the transformation from pilots to scalable, AI-driven workflows.

The role blends strategy, technology, and client leadership across complex environments. You’ll work with senior clients, own delivery quality, and feed insights back to product teams to ensure an enterprise-ready