Senior Strategist

Robots & Pencils

. Lead AI and digital strategy engagements end-to-end, from opportunity discovery and problem framing through prioritization, roadmap creation, and pilot planning .

Posted 10/15/2026full-timeRemote • Canada, United StatesSenior💰 $130,000 - $155,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading AI and digital strategy engagements, including opportunity discovery, roadmap creation, and stakeholder alignment. Proficient in utilizing AI tools for strategy and prototyping while ensuring responsible AI governance and effective communication with diverse audiences.

Highest-signal resume keywords

AI ConceptsBusiness AnalysisStakeholder EngagementPrototypingGovernance Frameworks

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Business AnalysisAI ConceptsPrompt EngineeringJourney MappingRoadmap CreationOpportunity SizingChange ManagementData ReadinessLightweight PrototypingEvaluation Frameworks

Soft Skills

CommunicationMentoringFacilitationRelationship BuildingCollaboration

Tools & Technologies

ClaudeClaude CodeCursorFigma AILangChainLangGraphVercel AI SDKAWS Strands

Industry Keywords

AI StrategyDigital SolutionsResponsible AIClient-Facing EnvironmentOperational Workflows

Tech Stack

Tools & technologies

AWS

About the role

Key responsibilities & impact

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 opportunities for automation, AI, and digital solutions
Build and present business cases that quantify value, define KPIs, and align executive and operational stakeholders
Produce lightweight prototypes, agent demonstrations, and proof-of-concept experiences
Partner with client subject-matter experts to create AI-ready assets, including prompt libraries, evaluation examples, and retrieval corpora
Define governance frameworks covering responsible AI, privacy, human-in-the-loop controls, and escalation paths
Test ideas with users and operational teams, iterating based on evidence
Translate between business and technical teams across design, data, engineering, and change management
Use AI tools and agentic frameworks to accelerate strategy and delivery
Lead executive briefings, ideation workshops, and process redesign sprints
Build trusted relationships with senior client stakeholders
Communicate complex findings, tradeoffs, and recommendations to executive and non-technical audiences
Lead prioritization and scoping decisions based on business value, feasibility, risk, and timelines
Frame engagements around outcomes and impact
Mentor junior analysts

Requirements

What you’ll need

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
Strong applied experience with AI tools for strategy, prototyping, and productivity, such as Claude, Claude Code, Cursor, and Figma AI
Hands-on experience with prompt engineering, agent workflows, and lightweight AI prototyping
Experience independently facilitating workshops and working sessions
Practical understanding of moving from pilot to scale, including data readiness, change management, adoption, and governance
Familiarity with agentic frameworks such as LangChain, LangGraph, Vercel AI SDK, and AWS Strands
Experience in a consulting or client-facing environment is a plus
Employment may be conditional upon successful completion of a background check
Must be based in Canada or the United States

Benefits

Comp & perks

Paid time off
Medical insurance
Dental insurance
Vision insurance
401(k) for eligible employees
Equal employment opportunities
Background check conducted in accordance with local legislation