FreeHire

Robots and Pencils

Director of Operations

Show

Director of Operations

Location: Remote – United States; preference for Detroit, Pittsburgh, Columbus, or Cleveland metro areas

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

We’re looking for a Director of Operations to scale and strengthen the systems, processes, and cross-functional infrastructure that power R&P’s growth. Reporting to the VP of Operations, you will be a key operational leader — translating strategic direction into disciplined execution, driving measurable improvements across financial performance, technology systems, and business operations.

This role spans the full breadth of operations: from standing up and managing critical business systems like our PSA and HRIS, to sharpening the operating model we have to price, sell, and retain clients. You will work closely with practice leads, finance, talent, and sales to eliminate friction, establish standards, and enable our teams to move faster and smarter. This role is right for someone who brings both strategic instincts and hands-on discipline — someone who thrives building structure in a high-growth, AI-forward professional services environment.

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. As Director of Operations, you shape the operational backbone that allows R&P to move at velocity, maintain quality, and grow sustainably. The work you do here has a direct line to client outcomes, team effectiveness, and the firm’s ability to compete and win.

What You’ll Do

Evolve Business Strategy

  • Lead the operational setup and go-to-market infrastructure for a managed services offering, partnering with sales, delivery, and finance to design scalable service models, SLAs, and supporting processes

  • Define and implement KPIs and benchmarking frameworks across delivery, talent, and finance that give leadership clear, consistent visibility into business health and performance trends

  • Partner with the VP of Operations, COO, and senior leadership to identify strategic opportunities, shape operational initiatives, and translate business priorities into executable plans

Process Improvement

  • Identify and eliminate operational bottlenecks across the firm by redesigning workflows, standardizing processes, and creating playbooks that improve consistency and quality at scale

  • Implement AI-powered tools and automation into administrative processes, with a focus on talent acquisition (sourcing, screening, scheduling) and talent experience (onboarding, engagement, offboarding)

  • Champion a culture of continuous improvement across operations, using data and feedback loops to drive iterative enhancements

Strategic Systems Management

  • Own end-to-end implementation and ongoing oversight of the firm’s PSA (Professional Services Automation) platform, ensuring it supports accurate project tracking, resource planning, utilization reporting, and billing workflows

  • Oversee the HRIS system, partnering with the talent team to ensure data integrity, compliance, and seamless integration across people operations

  • Lead the design and deployment of Slack automations that streamline internal workflows, reduce administrative overhead, and improve cross-functional coordination

  • Drive compliance-side readiness for AWS GenAIIC certification, coordinating across teams to document controls, meet requirements, and maintain certification standards

  • Manage IT cost strategy across applications and AI token consumption, identifying optimization opportunities and establishing governance frameworks that balance capability with spend

Financial Management

  • Partner with finance and practice leads to review and validate billing rates and delivery costs, ensuring pricing reflects market positioning, margin targets, and competitive realities

  • Develop and maintain practice- and vertical-level reporting standards that give leadership accurate, actionable financial visibility across the business

  • Implement and manage Work-in-Progress (WIP) tracking processes that improve revenue recognition accuracy, reduce billing lag, and surface project financial risk early

  • Design and build a Lifetime Value (LTV) and Customer Acquisition Cost (CAC) model for the sales team, enabling data-driven decisions on client investment, pipeline prioritization, and go-to-market strategy

Mergers and Acquisitions Integration

  • Partner with internal functional leaders to successfully integrate acquired company’s commercial, operations, technology, finance, and talent systems into Robots and Pencils’ existing systems

  • Lead full integration planning, including managing and coordinating workstreams, day-to-day tracking, and synergy planning.

  • Usher change management into the new organization



What You’ll Bring

  • 3+ years of experience in operations or strategy roles

  • Demonstrated experience owning and implementing business-critical systems

  • Strong financial acumen, including hands-on experience with revenue reporting, cost management, WIP tracking, and building analytical models (LTV, CAC, margin analysis)

  • Experience designing and deploying KPI frameworks and operational dashboards that translate complex data into clear business intelligence

  • Proven ability to design and scale operational processes in distributed, multi-geography organizations

  • Hands-on experience with workflow automation tools and AI-powered productivity tools

  • Exceptional communication and stakeholder management skills, with the ability to influence across all levels of the organization

Helpful Extras and Unique Skills

  • Experience with professional services

  • PSA platform (e.g., Certinia) experience



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 $115,000 USD - $180,000 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.