A natural match if you have experience leading AI and digital strategy engagements in enterprise settings.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Robots and Pencils via Greenhouse
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.
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 below range reflects the range of possible compensation for this role at the time of this posting. We may ultimately pay more or less than the posted range. This range may be modified in the future. An employee's position within the salary range will be based on several factors including, but not limited to, relevant education, qualifications, certifications, experience, skills, seniority, geographic location, performance, shift, travel requirements, sales or revenue-based metrics, any collective bargaining agreements, and business or organizational needs. The salary range for this role is $180.000 USD - $200.000 USD. We offer a comprehensive package of benefits including paid time off, medical/dental/vision insurance and 401(k) to eligible employees.
The below range reflects the range of possible compensation for this role at the time of this posting. We may ultimately pay more or less than the posted range. This range may be modified in the future. An employee's position within the salary range will be based on several factors including, but not limited to, relevant education, qualifications, certifications, experience, skills, seniority, geographic location, performance, shift, travel requirements, sales or revenue-based metrics, any collective bargaining agreements, and business or organizational needs. The salary range for this role is $190.000 CAD - $220.000 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.