VP, Strategy

Robots and Pencils

$150K — $180K *
US-AnywhereRemote in Canada
Business Services
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years of experience in business analysis or management consulting
  • Deep understanding of AI concepts like LLMs and responsible AI
  • Experience launching AI products using Microsoft Azure
  • Ability to lead discovery and strategy including journey mapping
  • Strong skills in creating narratives for executive stakeholders
  • Hands-on experience with prompt engineering and AI prototyping
  • Familiarity with agentic frameworks is a plus

Responsibilities

  • Lead end-to-end AI and digital strategy engagements
  • Map customer journeys to find automation opportunities
  • Build business cases defining KPIs and success for clients
  • Produce prototypes and proof-of-concept experiences
  • Partner with clients to create AI-ready knowledge assets
  • Define governance frameworks aligned to client risk postures
  • Test ideas early with real users to validate strategies
  • Translate between business and technical teams

Benefits

  • Flexible work arrangements
  • Opportunities for professional development
  • Collaborative team environment
  • Engage with leading-edge AI technology
  • Join a culture that values innovation and learning
Full Job Description
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

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