Enterprise AI Transformation Lead — Remote

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

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.