Job Details

Company:

Robots and Pencils

Position:

Senior Strategist

Location:

Canada - Remote, US - Remote

Position Overview We're looking for a Senior Business Analyst 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.

Why This Role Matters 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.

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

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

Robust applied experience with AI tools for strategy, prototyping, and productivity (e.g., Claude, Claude Code, Cursor, Figma AI)

Hands-on experience with prompt engineering, agent workflows, and lightweight AI prototyping

Experience independently facilitating workshops and working sessions that move

📌 Senior Strategist (Winnipeg)
🏢 F5 Remote Jobs
📍 Winnipeg