Senior Strategist

Job Details
Company:
Robots and Pencils
Position:
Senior Strategist
Location:
Canada - Remote, US - Remote
Position OverviewWe'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 MattersAt 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 DoCraft & 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
Strong 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 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 (e.G., LangChain, LangGraph, Vercel AI SDK, AWS Strands)
Experience in a consulting or client-facing environment is a plus
Helpful Extras and Unique SkillsYou’ll Do Well Here if You Are
A doer.
You see something broken and fix it. You'd rather move on clarity than wait for certainty.
A fast learner who knows you don't know everything.
The AI landscape changes weekly. You're senior enough to know better and curious enough to keep learning anyway.
Direct in a way that makes the work better.
You give honest feedback. You'd rather have the hard conversation than blow smoke.
Obsessed with craft.
You know genius is in the details. You ship exceptional, not perfect, and you don't put your name on work you wouldn't stand behind.
Built for ownership.
You honor commitments, admit mistakes fast, and back your teammates when a decision costs something. No handoffs, no finger-pointing.
All in.
You treat clients' businesses like your own. You take the work seriously without taking yourself seriously.
Resourceful when the budget, timeline, or team is tight.
Constraints don't slow you down. They sharpen you.
Glad to be in the room with people who care as much as you do.
Our teams average fifteen-plus years of experience. We hire people who push each other to do better work.
The salary range for this role is $130.000 USD - $155.000 USD. We offer a comprehensive package of benefits including paid time off, medical/dental/vision insurance and 401(k) to eligible employees.
The salary range for this role is $140.000 CAD - $170.000 CAD. We offer a comprehensive package of benefits including paid time off, medical/dental/vision insurance and 401(k) to eligible employees.
An offer of employment may be conditional upon successful completion of a background check in accordance with local legislation and our candidate privacy notice. Your current employer will not be contacted without your permission. We are committed to ensuring equal employment opportunities for all job applicants and employees. Employment decisions are based upon job-related reasons regardless of an applicant's race, color, religion, sex, sexual orientation, gender identity, age, national origin, disability, marital status, genetic information, protected veteran status, or any other status protected by law.
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