---
title: 'VP, Strategist at Robots and Pencils'
canonical: 'https://feeny.ai/job/vp-strategist-robots-and-pencils-united-states-sv8bhwsfhx5z'
type: 'job'
last_seen: '2026-11-05'
---

# VP, Strategist at Robots and Pencils

- **Company:** Robots and Pencils
- **Location:** United States
- **Work type:** remote
- **Posted:** 2026-09-25
- **Last confirmed live:** 2026-11-05
- **Apply:** https://job-boards.greenhouse.io/robotsandpencils/jobs/5435381008

## Job description

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 - $210.000 USD.  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.

## About Robots and Pencils

## Company Overview
- **One-liner**: Robots & Pencils is an Applied AI Engineering Partner that builds generative and agentic AI systems for enterprise clients, taking AI from pilot to production quickly.
- **Entity Type**: Private (Bootstrapped/Organic Growth)
- **Headquarters**: Chagrin Falls, Ohio, United States
- **Founded**: 2009
- **Founders**: Len Pagon (CEO), Nathan Carmon

## Core Business
- **Primary industry/industries**: IT Services and IT Consulting, Applied AI Engineering, Cloud-Native Development
- **Target customers**: Enterprise clients in Financial Services, Healthcare, Education, Energy, Retail & Consumer Goods, High Tech, and Transportation
- **Mission or purpose statement**: "We build smart systems for a human world" — blending the logic of machines with the creativity of humans to help organizations modernize platforms, design cloud-native applications, and unlock the real-world value of AI.

## Products & Services
- **Applied AI Engineering**: Building generative and agentic AI systems on Amazon Bedrock and Amazon Bedrock AgentCore, with memory, observability, and security built in from the start. Focused on taking AI from pilot to production quickly.
- **Cloud-Native AWS Modernization**: Re-architecting AWS environments from EC2/ECS to serverless-native infrastructure. Migrating legacy systems to cloud-native AWS, beyond lift-and-shift.
- **The Sharpening Sprint™**: A structured engagement to surface the strongest AI use cases for a client and deliver a sequenced build plan.
- **UX/UI Design & Product Strategy**: A creative team of product owners, researchers, UX designers, and visual designers who craft seamless experiences.
- **Legacy Platform Modernization**: Refactoring aging platforms and designing cloud-native applications across industries.

## Market Standing
- **Valuation/Market Cap**: Not publicly available (privately held)
- **Key Metric**: Annual Revenue of **$21.5M** (estimated) [ca.linkedin.com](https://ca.linkedin.com/company/robots-and-pencils)
- **Notable Investors/Partners**: AWS (Advanced Tier Services Partner and Inaugural AWS Pattern Partner)
- **Growth Signals**: Headcount of ~115 employees (+35.1% YoY, +39 people) [ca.linkedin.com](https://ca.linkedin.com/company/robots-and-pencils); 23,753 LinkedIn followers (+55.2% yearly growth); 77M+ users reached worldwide across launched apps; 25 patents & published works; 5 apps hit #1 in the App Store

## Competitive Advantages
- **Applied AI Engineering Focus**: Specializes exclusively in taking generative and agentic AI from pilot to live, fast — a nimble, high-velocity alternative to traditional global systems integrators.
- **AWS Pattern Partner**: One of only 11 inaugural AWS Pattern Partners selected from the AWS Partner Network, signaling deep technical partnership and trust.
- **Senior-Led Teams**: Operates through small, senior teams (15+ years average experience per team member) rather than massive consulting organizations, ensuring high-quality delivery.
- **Human-Centered Design**: Blends elite engineering talent with world-class UX design, differentiating from pure technical consultancies.
- **Proven Track Record**: 77M+ users reached worldwide, 25 patents & published works, and multiple #1 App Store launches.

## Strategic Focus
- **Agentic AI on AWS**: Building agentic systems on Amazon Bedrock and Amazon Bedrock AgentCore with memory, observability, and security built in from the start.
- **Production-Ready AI**: Focused on taking AI from pilot to production in weeks, not months, with a strong emphasis on compliance and regulatory environments (Financial Services, Healthcare).
- **Industry Expansion**: Serving Financial Services, Health Tech, Education, Energy, Retail & Consumer Goods, and High Tech — industries where AI agents create exponential value.
- **Global Delivery Network**: Operating delivery centers across the U.S., Canada, Eastern Europe, and Latin America to serve enterprise clients worldwide.

## Why Work Here
- **Culture**: Described as "wicked smart, wildly curious, ready to build" — a culture that values curiosity, collaboration, and impact. The company emphasizes "always learning" and invests in personal and professional growth.
- **Work Model**: Hybrid and remote-friendly. "Whether you are co-located in one of our offices or remote first, we prioritize how teams are set up to focus in on collaboration for successful delivery." [robotsandpencils.com](https://robotsandpencils.com/careers/)
- **Benefits**: Salary continuation and protected leave for parents (birth, spouse, and adoptive); health & wellness benefits; flexible hours; paid time off (vacation, sick, personal leave, flexible holidays).
- **Engineering Culture**: Described as a team of "tech wizards creating digital magic" — frontend, backend, mobile, and full-stack developers working on cutting-edge AI and cloud-native projects. The hiring process includes a pre-screen assessment, skills assessment, and deep dive interview to evaluate culture addition, communication, and technical fit.
- **Global Team**: Delivery centers in the U.S., Canada, Ukraine, Colombia, and the Philippines, offering a diverse, international work environment.

## Sources
1. [robotsandpencils.com](https://robotsandpencils.com/)
2. [robotsandpencils.com/about](https://robotsandpencils.com/about/)
3. [robotsandpencils.com/careers](https://robotsandpencils.com/careers/)
4. [job-boards.greenhouse.io/robotsandpencils](http://job-boards.greenhouse.io/robotsandpencils)
5. [ca.linkedin.com/company/robots-and-pencils](https://ca.linkedin.com/company/robots-and-pencils)

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