VP, AI Strategy & Enterprise Growth

Robots & Pencils; Friendly (MD); On-site; USD 180,000 - 210,000; Full time

Benefits offered by this job

Paid time off

Medical/dental/vision insurance

401(k) plan

Job summary

Robots & Pencils seeks a VP, Strategist to define strategy and lead client engagements, shaping the direction of major initiatives and building senior relationships. You will own strategic engagements end-to-end, from discovery to scale, with a focus on AI strategy and governance.

You will mentor analysts, contribute to practice growth, and craft reusable strategy assets that help scale client impact across enterprises in a fast-moving AI landscape.

Qualifications

• 7+ years in management consulting, product strategy, AI strategy, or a related field.
• Expert-level understanding of AI concepts including LLMs, RAG, agentic systems, evaluation frameworks, responsible AI, and enterprise AI operating models.
• Proven track record leading AI and digital strategy engagements end-to-end across complex, multi-stakeholder organizations.
• Expert applied experience with AI tools for strategy, prototyping, and productivity (e.g., Claude, Claude Code, Cursor, Figma AI).
• Hands-on experience with agentic frameworks as a core part of strategy and prototyping work (e.g., LangChain, LangGraph, Vercel AI SDK, AWS Strands).
• Experience designing evaluation strategies and guiding conversations on model calibration and AI system performance.
• Strong executive communication and advisory skills with a track record of influencing senior leaders across business and IT.
• Experience creating reusable strategy assets, practice accelerators, and reference architectures.
• Experience contributing to business development, proposals, or practice growth.
• Track record of mentoring strategy practitioners and lifting team quality and craft.

Responsibilities

• Define AI and digital strategy for major client engagements, owning the opportunity portfolio from discovery through scale roadmaps.
• Lead complex, multi-stakeholder strategy engagements independently, driving alignment across executive, operational, and technical audiences.
• Build and present board- and executive-level business cases with clear tradeoffs, value quantification, and pragmatic recommendations.
• Design and lead evaluation (Evals) strategy to improve AI system effectiveness, accuracy, and calibration across client programs.
• Create reusable strategy accelerators including playbooks, reference architectures, evaluation templates, and agent patterns that help clients scale consistently.
• Define AI governance and responsible AI frameworks that fit the client's regulatory context, risk posture, and operational realities.
• Make ideas real quickly by building agent workflows, conversational experiences, and AI-enabled demonstrations using modern tools.
• Bring an AI-forward mindset to your daily work, using tools like Claude, Claude Code, Cursor, and Figma AI — and agentic frameworks as a core part of how strategy gets built and validated (e.g., LangChain, LangGraph, Vercel AI SDK, AWS Strands).

Skills

Strategic leadership

Executive communication

AI strategy

Client engagement

Project management

Job description

Robots & Pencils seeks a VP, Strategist to define strategy and lead client engagements, shaping the direction of major initiatives and building senior relationships. You will own strategic engagements end-to-end, from discovery to scale, with a focus on AI strategy and governance.

You will mentor analysts, contribute to practice growth, and craft reusable strategy assets that help scale client impact across enterprises in a fast-moving AI landscape.