Senior Strategist (AI)

Location: Remote in Canada or the United States

Salary: USD $130,000–$155,000 annually; CAD $140,000–$170,000 annually, depending on location and qualifications.

Company

Robots & Pencils is an applied AI engineering firm that designs and ships AI co-workers and digital solutions for enterprise operations.

What you will do

• Lead AI and digital strategy engagements from opportunity discovery and problem framing through prioritization, roadmaps, and pilot planning.
• Map customer journeys, operational workflows, and decision points to identify measurable opportunities for automation and AI.
• Build business cases, define KPIs, and align executive and operational stakeholders on outcomes.
• Create lightweight prototypes, agent demonstrations, proof-of-concept experiences, prompt libraries, evaluation examples, and retrieval corpora.
• Define responsible AI governance covering privacy, human-in-the-loop controls, risk, and escalation paths.
• Facilitate executive briefings and workshops, mentor junior analysts, and connect strategy with design, data, engineering, and change management.

Requirements

• 5+ years of experience in business analysis, management consulting, product strategy, or a related role.
• Deep understanding of LLMs, RAG, copilots, agents, evaluation frameworks, and responsible AI principles.
• Experience leading discovery and strategy end-to-end, including stakeholder interviews, journey mapping, opportunity sizing, prioritization, and roadmap creation.
• Experience creating executive-ready narratives, facilitating workshops, and aligning senior business and IT stakeholders.
• Hands-on experience with AI tools such as Claude, Claude Code, Cursor, and Figma AI, plus prompt engineering, agent workflows, and lightweight AI prototyping.
• Practical understanding of data readiness, change management, adoption, governance, and scaling AI pilots; familiarity with LangChain, LangGraph, Vercel AI SDK, or AWS Strands.

Nice to have

• Experience in a consulting or client-facing environment.

Culture & Benefits

• Work with cross-functional teams combining UX, strategy, and senior engineering expertise.
• Build production-ready AI systems for enterprise workflows, with typical delivery timelines of 30–45 days.
• Paid time off and medical, dental, and vision insurance for eligible employees.
• 401(k) benefits for eligible employees.
• Employment may be conditional on a background check in accordance with local legislation.