Director of Engineering

Director of Engineering

Location: This position can be remote and requires travel


Company Overview

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
The Director of Engineering is a senior leadership role at Robots & Pencils, responsible for the technical health, delivery performance, and talent growth of a geographically aligned engineering organization. This is a director-level position with regional P&L accountability, client-facing responsibility, and direct influence over how R&P delivers AI-forward engineering at scale.

We're looking for someone who has been an engineer - who has shipped real software and led real projects - and who has evolved into a leader that builds teams, develops talent, and drives outcomes. You bring a consulting mindset, a bias for action, and the kind of deep AI and agentic development expertise that can change how a client operates. You don't just stay current on AI tools; you teach others how to use them, set the standard, and demonstrate what great looks like every day.

This role requires 10+ years of overall engineering experience, with at least 3 years in an Engineering Manager or Director capacity leading multi-person technical teams.

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
Lead and grow a geographically aligned engineering organization at the director level, owning regional P&L, setting the standard for AI-forward engineering, and ensuring successful delivery of client and internal initiatives while developing technical talent and maintaining engineering excellence.

Key Responsibilities

• Lead, coach, and grow a geographically aligned engineering organization, developing technical talent and the next layer of engineering leaders.
• Champion adoption of AI-forward tools and AI-assisted delivery, raising both velocity and expertise.
• Partner with sales, verticals, and practice leaders to align engineering capacity with business demand and staff teams with the right skills and experience.
• Foster a culture of technical excellence, ownership, and continuous improvement, where engineers verify and stand behind AI-assisted work.
• Drive adoption of engineering standards, security requirements, and quality practices across an AI-augmented software development lifecycle.
• Use data to manage delivery performance, resource utilization, and team health, layering AI-assisted delivery signals onto core engineering metrics.
• Build team AI capability through coaching, upskilling, and knowledge sharing, leaving no engineer behind as tools and practices evolve.
• Support workforce planning, recruiting, onboarding, performance management, and succession planning for future technical leaders.
• Collaborate with other Engineering Directors and Managers to keep standards consistent across regions, and escalate and resolve staffing, delivery, and personnel challenges as needed.
• Own regional P&L, including revenue accountability, margin performance, and resource investment decisions for the engineering organization.
• Actively participate in recruiting and interviewing for senior technical roles, evaluating candidates against both technical and cultural standards and partnering with Talent to build engineering hiring pipelines.
• Set the standard for AI-forward engineering practice - using tools like Claude and Cursor with sophistication, modeling what great looks like, and helping the team adopt AI tools effectively and with confidence.
• Lead the design and delivery of AI/ML systems end-to-end, from architecture decisions through production deployment, bringing both strategic vision and hands-on judgment to every phase.

What You'll Bring

• 10+ years of overall engineering experience, including at least 3 years in an Engineering Manager or Director role leading multi-person technical teams, with a hands-on background building software and leading projects earlier in your career.
• Strong people leadership, coaching, and talent development skills, with a track record of building high-performing teams.
• Working understanding of modern software development, cloud platforms, and AI-assisted engineering practices.
• Extremely strong AI and agentic development skills - not just familiarity but the ability to teach others, set standards, and create measurable impact at the client level using tools like Claude, Cursor, and other AI-forward platforms.
• Experience managing distributed or geographically dispersed teams and aligning capacity with shifting demand.
• Fluency with engineering metrics and data-informed delivery management.
• Excellent communication, stakeholder management, and organizational skills.
• Consulting mindset, whether through direct experience at a firm or in a role servicing external clients or internal business units - you understand how to earn trust, manage expectations, and deliver value in client-facing contexts.
• Strong focus on team and talent development, with a demonstrated ability to grow engineers into leaders and build high-trust, high-performance teams over time.
• AI-forward thinker who stays ahead of the curve, brings genuine enthusiasm for what's possible, and can translate that into practical outcomes for clients and the team.
• Strategic thinker with a bias for action - you can set direction, build a plan, and then roll up your sleeves to make it happen without waiting for perfect conditions.
• Practical hands-on skills in leading the design and delivery of AI/ML systems, including agentic architectures, LLM integration, and production deployment on modern cloud platforms.

Success Measures

• Talent engagement, retention, and growth of technical talent
• Regional P&L performance, including revenue contribution, margin health, and cost efficiency of the engineering organization
• Quality and speed of engineering hiring, including interviewing throughput and calibration consistency for senior technical roles
• Delivery quality, velocity, and client satisfaction
• Adoption and effective use of AI-forward tools and AI-assisted delivery across the team
• Resource utilization and staffing effectiveness against demand
• Career progression and leadership development of team members
• Regional engineering capacity, capability maturity, and readiness

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.