Robots and Pencils

applied AI engineering

SeniorStrategist

Calgary, Alberta, Canada
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Senior candidates.

The Brief

“Senior Strategist at Robots and Pencils. Skills: AI and digital strategy, end-to-end engagement leadership, AI product prototyping and production, stakeholder alignment, governance framework definition. Lead AI and digital strategy engagements end-to-end. Map customer journeys, operational workflows, and decision points”

What You'll Achieve.

deliver measurable results for our clients; get AI into production fast and keep it there; deliver a clear, actionable plan; shape recommendations; facilitate high-impact client sessions that turn ambiguity into direction; define KPIs, and align executive and operational stakeholders on what success looks like; make strategy tangible and testable for clients; move faster than traditional consulting cycles; move groups from ambiguity to a shared plan; move groups to clarity quickly; shape how AI systems integrate into enterprise operations; shape how teams move at real velocity; shape how products create measurable impact for clients and the people they serve; ship production-ready AI in 30 to 45 days

Industry & Context.

applied AI engineering
Problems you'll solve

framing the problem; turn ambiguity into direction; navigate complexity; identify where automation, AI, and digital solutions create measurable business lift

What They're Looking For.

Must Have

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, 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, 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, Experience in a consulting or client-facing environment

Nice to Have

Experience with Microsoft Azure Foundry and Azure Foundry Agent Service as the core cloud platform, Familiarity with agentic frameworks

What You'll Do.

Lead AI and digital strategy engagements end-to-end

Map customer journeys

operational workflows

Build and present compelling business cases

Produce lightweight prototypes

and proof-of-concept experiences

Partner with client SMEs to encode institutional knowledge into AI-ready assets

Define practical governance frameworks

Shrink feedback loops by testing ideas early

Translate between business and technical teams

Bring an AI-forward mindset to daily work

Independently lead high-impact client sessions

Build trusted relationships with senior client stakeholders

Communicate complex findings

and recommendations clearly

Lead prioritization and scoping decisions

Frame every engagement in terms of outcomes and impact

Begin mentoring junior analysts

How You'll Work.

Team & Collaboration

work as the lead analyst on a cross-functional team; collaborate closely with strategists, designers, engineers, and delivery leads; Translate between business and technical teams, ensuring strategy connects cleanly to delivery across design, data, engineering, and change management

Communication Scope

Build and present compelling business cases; Communicate complex findings, tradeoffs, and recommendations clearly to executive and non-technical audiences; Independently lead high-impact client sessions including executive briefings, ideation workshops, and process redesign sprints

Process & Methodology

prioritization, roadmap creation, pilot planning, scoping decisions, balancing business value, feasibility, risk, and delivery timelines

Full Job Description

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

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