Senior Strategist

Robots and Pencils•Calgary, AB

About The Position

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.

Requirements

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

Nice To Haves

Experience in a consulting or client-facing environment is a plus

Responsibilities

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
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
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