Senior Strategist

Robots & Pencils is an applied AI engineering firm building the next frontier of business architecture. We design and ship AI co-workers that integrate into enterprise operations and deliver measurable results for our clients. We're all in on AWS, combining deep UX capability with senior engineering talent to get AI into production fast and keep it there. We’ve earned the trust of leaders across Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, and Manufacturing and more, and earned a reputation as the nimble alternative to traditional global systems integrators. Founded in 2009, with delivery centers in Canada, the United States, Eastern Europe, and Latin America, we are smaller, faster, and more senior by design. Our teams average 15+ years of experience. We move fast, sweat the details, and build things that actually ship.

About the role
We're looking for a Senior Strategist to lead strategy and discovery work end-to-end across complex client engagements. This role is ideal for an experienced analyst and strategist who can independently own the full arc of an engagement — from framing the problem through delivering a clear, actionable plan — while building trusted relationships with senior client stakeholders.
In this role, you will work as the lead analyst on a cross-functional team, driving discovery, shaping recommendations, and facilitating high-impact client sessions that turn ambiguity into direction. You'll collaborate closely with strategists, designers, engineers, and delivery leads, and bring the experience and judgment to navigate complexity, competing priorities, and high-stakes decisions with confidence.

What You’ll Do
Craft & Delivery

• Lead AI and digital strategy engagements end-to-end, from opportunity discovery and problem framing through prioritization, roadmap creation, and pilot planning
• Map customer journeys, operational workflows, and decision points to identify where automation, AI, and digital solutions create measurable business lift
• Build and present compelling business cases that quantify value, define KPIs, and align executive and operational stakeholders on what success looks like
• Produce lightweight prototypes, agent demonstrations, and proof-of-concept experiences that make strategy tangible and testable for clients
• Partner with client SMEs to encode institutional knowledge into AI-ready assets including prompt libraries, evaluation examples, and retrieval corpora
• Define practical governance frameworks aligned to the client's risk posture covering responsible AI principles, privacy, human-in-the-loop controls, and escalation paths
• Shrink feedback loops by testing ideas early with real users and operational teams, iterating based on evidence rather than assumptions
• Translate between business and technical teams, ensuring strategy connects cleanly to delivery across design, data, engineering, and change management
• Bring an AI-forward mindset to your daily work, using tools like Claude, Claude Code, Cursor, and Figma AI — and agentic frameworks where relevant — to move faster than traditional consulting cycles

Collaboration & Communication

• Independently lead high-impact client sessions including executive briefings, ideation workshops, and process redesign sprints that move groups from ambiguity to a shared plan
• Build trusted relationships with senior client stakeholders, serving as a reliable, consultative partner throughout the engagement
• Communicate complex findings, tradeoffs, and recommendations clearly to executive and non-technical audiences

Leadership & Influence

• Lead prioritization and scoping decisions by balancing business value, feasibility, risk, and delivery timelines
• Frame every engagement in terms of outcomes and impact, pushing back on solution-first thinking where needed
• Begin mentoring junior analysts, sharing knowledge and supporting their growth in craft and client skills

What You’ll Bring

• 5+ years of experience in business analysis, management consulting, product strategy, or a related role
• Deep understanding of AI concepts including LLMs, RAG, copilots, agents, evaluation frameworks, and responsible AI principles
• Experience prototyping and launching AI products and workflows in production with Microsoft Azure Foundry and Azure Foundry Agent Service as the core cloud platform
• Demonstrated ability to lead discovery and strategy end-to-end including stakeholder interviews, journey mapping, opportunity sizing, prioritization, and roadmap creation
• Experience creating executive-ready narratives and aligning senior stakeholders across business and IT
• Strong applied experience with AI tools for strategy, prototyping, and productivity
• Hands-on experience with prompt engineering, agent workflows, and lightweight AI prototyping
• Experience independently facilitating workshops and working sessions that move groups to clarity quickly
• Practical understanding of what it takes to move from pilot to scale including data readiness, change management, adoption, and governance
• Familiarity with agentic frameworks
• Experience in a consulting or client-facing environment is a plus

Why Join Robots & Pencils?

At Robots & Pencils, we design AI systems for a human world. Our name says it all. Robots and pencils means engineering paired with creativity, because every agent we ship has to work for real people in real workflows. That balance is baked into how we operate. Every role here contributes directly to that mission. Here, you shape how AI systems integrate into enterprise operations, how teams move at real velocity, and how products create measurable impact for clients and the people they serve. We ship production-ready AI in 30 to 45 days. That pace demands people who take ownership, lead with craft, and care deeply about what they put their name on.