Senior Strategist

Company Overview

Robots & Pencils is an applied AI engineering firm focused on building the next wave of business architecture. The team creates AI co-workers that plug into enterprise operations and produce measurable client outcomes. The company works heavily with AWS, combining strong UX capability with senior engineering depth to move AI into production quickly and keep it running reliably. Since its founding in 2009, it has supported clients across consumer products, retail, education, energy, financial services, healthcare, manufacturing, and other sectors. Delivery centers are located in Canada, the United States, Eastern Europe, and Latin America. The organization positions itself as a faster, more senior alternative to large global systems integrators, with teams averaging 15+ years of experience.

Role Summary

Robots & Pencils is seeking a Senior Strategist to own strategy and discovery work from start to finish across complex client engagements. This position suits an experienced analyst and strategist who can independently manage the entire engagement lifecycle, from defining the problem to delivering an actionable plan, while building strong relationships with senior client stakeholders.

In this role, you will act as the lead analyst on a cross-functional team, guiding discovery, shaping recommendations, and facilitating client sessions that convert uncertainty into clear direction. You will work closely with strategists, designers, engineers, and delivery leads, bringing judgment and experience to navigate complexity, competing priorities, and high-stakes decisions.

What You’ll Do

• Own AI and digital strategy engagements end to end, including opportunity discovery, problem framing, prioritization, roadmap development, and pilot planning.
• Analyze customer journeys, operational workflows, and decision points to identify where automation, AI, and digital tools can create measurable business value.
• Develop and present business cases that define value, establish KPIs, and align executive and operational stakeholders around success measures.
• Create simple prototypes, agent demos, and proof-of-concept experiences that make strategic ideas concrete and testable for clients.
• Work with client subject-matter experts to convert institutional knowledge into AI-ready assets such as prompt libraries, evaluation samples, and retrieval corpora.
• Design practical governance approaches suited to the client’s risk profile, including responsible AI practices, privacy, human oversight, and escalation routes.
• Shorten feedback cycles by validating ideas early with real users and operational teams, then refining based on evidence.
• Bridge business and technical teams so strategy translates smoothly into delivery across design, data, engineering, and change management.
• Use an AI-first mindset in daily work, leveraging tools such as Claude, Claude Code, Cursor, Figma AI, and relevant agentic frameworks to work faster than traditional consulting methods.
• Run high-impact client sessions independently, including executive briefings, ideation workshops, and process redesign sprints that lead groups toward a shared plan.
• Build trusted, consultative relationships with senior client stakeholders throughout the engagement.
• Present complex findings, trade-offs, and recommendations in a clear way for executives and non-technical audiences.
• Support prioritization and scope decisions by weighing business value, feasibility, risk, and delivery timing.
• Keep every engagement focused on outcomes and impact, and challenge solution-first thinking when appropriate.
• Start mentoring junior analysts by sharing knowledge and helping them grow in client-facing and craft skills.

What You’ll Bring

• At least 5 years of experience in business analysis, management consulting, product strategy, or a similar field.
• Strong knowledge of AI concepts such as LLMs, RAG, copilots, agents, evaluation frameworks, and responsible AI principles.
• Experience prototyping and launching AI products and workflows in production using Microsoft Azure Foundry and Azure Foundry Agent Service as the main cloud platform.
• Proven ability to lead discovery and strategy work end to end, including stakeholder interviews, journey mapping, opportunity sizing, prioritization, and roadmap design.
• Experience writing executive-level narratives and aligning senior stakeholders across business and IT.
• Applied use of AI tools for strategy, prototyping, and productivity.
• Hands-on familiarity with prompt engineering, agent workflows, and lightweight AI prototyping.
• Ability to independently facilitate workshops and working sessions that quickly create clarity.
• Practical understanding of what is needed to move from pilot to scale, including data readiness, change management, adoption, and governance.
• Familiarity with agentic frameworks.
• Client-facing or consulting experience is considered an advantage.

Why Join Robots & Pencils

The company builds AI systems for people, not just for technology’s sake. Its work blends engineering with creativity so that every shipped agent functions within real human workflows. Team members help shape how AI fits into enterprise operations, how teams work at real speed, and how products create measurable impact for clients and end users. The organization ships production-ready AI in 30 to 45 days, which calls for people who take ownership, care about quality, and stand behind the work they deliver.