Director of Engineering

Robots and Pencils

$130K — $180K *
Enterprise Technology
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 10+ years of engineering experience, with at least 3 years in a managerial or director-level role overseeing technical teams.
  • Strong leadership skills with a proven track record in talent development.
  • Deep familiarity with AI-assisted engineering tools and practices.
  • Experience managing remote or geographically distributed teams.
  • Proficient in engineering metrics and data-driven performance management.
  • Excellent communication and stakeholder management abilities.
  • Consulting mindset with experience in external client interactions.

Responsibilities

  • Lead and grow a geographically aligned engineering organization, developing technical talent and future leaders.
  • Champion the use of AI-forward tools to enhance delivery speed and quality.
  • Align engineering capacity with business demand through collaborative partnerships with sales and other leaders.
  • Foster a continuous improvement culture, emphasizing technical excellence and ownership among engineers.
  • Drive the adoption of engineering standards and best practices across teams.
  • Utilize data to optimize delivery performance and team health metrics.
  • Facilitate workforce planning and recruitment for senior technical roles.

Benefits

  • Remote work flexibility with travel requirements.
  • Opportunities for leadership development and talent growth.
  • Exposure to cutting-edge AI and engineering practices.
  • Engagement with a team of experienced professionals.
  • Participation in a culture of continuous improvement and technical excellence.
Full Job Description
Director of Engineering

Location: This position can be remote and requires travel

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.

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.

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