VP, Strategist

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. 

Position Overview 

We're looking for a VP, Strategist to define strategy and lead complex client engagements from the front. This role marks a meaningful shift from executing strategy work to shaping it — owning the strategic direction of major engagements, building senior client relationships, and contributing to how R&P's strategy practice grows and evolves. 

In this role, you will operate as the senior strategy voice on a cross-functional team, setting direction, aligning stakeholders, and driving outcomes from discovery through delivery. You'll partner closely with client leadership, mentor other analysts and strategists, and bring the depth of experience to navigate the most complex, ambiguous problems with confidence and clarity. 

Why This Role Matters 

At 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 Do 

Craft & Delivery 

• Define AI and digital strategy for major client engagements, owning the opportunity portfolio from discovery through scale roadmaps  

• Lead complex, multi-stakeholder strategy engagements independently, driving alignment across executive, operational, and technical audiences  

• Build and present board- and executive-level business cases with clear tradeoffs, value quantification, and pragmatic recommendations  

• Design and lead evaluation (Evals) strategy to improve AI system effectiveness, accuracy, and calibration across client programs  

• Create reusable strategy accelerators including playbooks, reference architectures, evaluation templates, and agent patterns that help clients scale consistently  

• Define AI governance and responsible AI frameworks that fit the client's regulatory context, risk posture, and operational realities  

• Make ideas real quickly by building agent workflows, conversational experiences, and AI-enabled demonstrations using modern tools  

• Bring an AI-forward mindset to your daily work, using tools like Claude, Claude Code, Cursor, and Figma AI — and agentic frameworks as a core part of how strategy gets built and validated (e.g., LangChain, LangGraph, Vercel AI SDK, AWS Strands)  

Collaboration & Communication 

• Serve as a senior strategic partner to client leadership, building long-term trusted relationships grounded in business outcomes and honest counsel  

• Lead the most complex client sessions including executive briefings, strategic planning workshops, and multi-stakeholder alignment forums  

• Communicate strategy, tradeoffs, and recommendations with clarity and conviction at the executive level 

Leadership & Influence 

• Establish strategic delivery standards and ways of working on the engagements you support 

• Mentor senior and mid-level analysts, helping them grow their strategic thinking, client skills, and delivery impact 

• Contribute to business development, proposals, and the growth of R&P's strategy practice 

• Act as an escalation point on complex scope, prioritization, and strategic framing challenges 

What You’ll Bring 

• 7+ years of experience in management consulting, product strategy, AI strategy, or a related field  

• Expert-level understanding of AI concepts including LLMs, RAG, agentic systems, evaluation frameworks, responsible AI, and enterprise AI operating models  

• Demonstrated track record of leading AI and digital strategy engagements end-to-end across complex, multi-stakeholder organizations  

• Expert applied experience with AI tools for strategy, prototyping, and productivity (e.g., Claude, Claude Code, Cursor, Figma AI)  

• Hands-on experience with agentic frameworks as a core part of strategy and prototyping work (e.g., LangChain, LangGraph, Vercel AI SDK, AWS Strands)  

• Experience designing evaluation strategies and guiding conversations on model calibration and AI system performance  

• Strong executive communication and advisory skills with a track record of influencing senior leaders across business and IT  

• Experience creating reusable strategy assets, practice accelerators, and reference architectures  

• Experience contributing to business development, proposals, or practice growth  

• Track record of mentoring strategy practitioners and lifting team quality and craft 

Helpful Extras and Unique Skills 

You’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.