VP, Strategist (AI)

Location: Remote in the United States or Canada

Salary: $180,000–$200,000 USD annually for the United States; CAD 190,000–220,000 annually for Canada.

Company

Robots & Pencils is an applied AI engineering firm building and deploying AI co-workers and digital solutions for enterprise operations.

What you will do

• Define AI and digital strategy for major client engagements from discovery through scale roadmaps.
• Lead complex, multi-stakeholder engagements and align executive, operational, and technical audiences.
• Build and present executive- and board-level business cases with quantified value, tradeoffs, and pragmatic recommendations.
• Design evaluation strategies to improve AI system effectiveness, accuracy, and calibration.
• Create reusable playbooks, reference architectures, evaluation templates, and agent patterns.
• Define responsible AI governance frameworks and prototype agent workflows, conversational experiences, and AI-enabled demonstrations.

Requirements

• 7+ years of experience in management consulting, product strategy, AI strategy, or a related field.
• Expert understanding of LLMs, RAG, agentic systems, evaluation frameworks, responsible AI, and enterprise AI operating models.
• Experience leading AI and digital strategy engagements across complex, multi-stakeholder organizations.
• Hands-on experience with Claude, Claude Code, Cursor, Figma AI, LangChain, LangGraph, Vercel AI SDK, or AWS Strands.
• Strong executive communication, advisory, mentoring, business development, and practice-growth experience.
• Must be located in the United States or Canada.

Nice to have

• Experience creating reusable strategy assets, practice accelerators, and reference architectures.
• Experience guiding conversations on model calibration and AI system performance.

Culture & Benefits

• Remote work for employees in the United States or Canada.
• Work focused on shipping production-ready AI systems in 30–45 days.
• Paid time off and medical, dental, and vision insurance for eligible employees.
• 401(k) benefits for eligible employees.
• Collaborative teams with an average of 15+ years of experience.