Director, Revenue Operations Paper - United States of America Canada Remote

Director, Revenue Operations

Paper is reimagining how schools support students so that every learner can reach their full potential. Our vision is a world where every student receives timely, personalized, and relevant academic support. We offer a suite of scalable solutions including 24/7 tutoring, writing feedback, math practice, college and career support, and AI-powered instructional tools that provide personalized support to all students, including multilingual learners. Our GROW high-impact tutoring program accelerates learning through targeted small-group instruction, delivers measurable gains in student achievement, and eases teacher workloads. Trusted by 500+ school districts across 40+ states and backed by leading investors including IVP, Sapphire Ventures, Framework Capital, and Reach Capital, we're pursuing a bold goal: to drive the best academic outcomes for as many students as possible.

About the role

The Director, Revenue Operations will own the revenue operating system end-to-end. This includes pipeline management, forecasting, sales process, tooling, and GTM analytics. You will set the strategy and execute it. This is a player-coach role in a Series A environment. You will operate at both a strategic and tactical level, building the foundation while driving day-to-day execution. This role is AI-forward. You will leverage AI tools and automation to improve forecasting accuracy, increase rep productivity, and scale operations without adding headcount.

What you'll do

Pipeline & Forecasting

• Own pipeline health, stage discipline, and forecast accuracy
• Leverage AI to identify deal risk, slippage, and forecast gaps
• Lead weekly pipeline and forecast reviews with data-driven insights

Sales Process & GTM Operations

• Design and optimize the sales process across new business and expansion
• Implement and enforce CRM stage definitions, entry, and exit criteria
• Use AI to streamline workflows, reduce manual updates, and improve compliance
• Drive operating cadence (weekly metrics, monthly reviews)
• Support deal structuring, approvals, and contract workflows (deal desk)

Systems & Tools

• Own Salesforce architecture, data model, and governance end-to-end
• Evaluate and deploy AI-enabled GTM tools (forecasting, enrichment, call intelligence, workflow automation)
• Automate reporting, data capture, and repetitive tasks
• Ensure clean data flow across Sales, Marketing, CS, and Finance systems

Analytics & Insights

• Define and track key funnel metrics (conversion, velocity, pipeline coverage)
• Use AI and advanced analytics to identify patterns, performance drivers, and opportunities
• Translate insights into clear actions for GTM teams
• Accountable for data definitions, quality, and governance across all GTM systems

Planning & Capacity

• Support annual planning, territory design, and quota setting
• Model pipeline coverage, hiring needs, and productivity scenarios
• Use data and AI-assisted modeling to improve planning accuracy

Enablement Support

• Partner with Sales leadership on onboarding and ongoing enablement
• Equip reps with AI tools and workflows that increase selling time
• Reduce friction in the day-to-day sales motion

What success looks like

• Accurate and predictable forecasts
• Clean, reliable pipeline with clear next steps
• Improved conversion rates and shorter sales cycles
• Strong data integrity across systems
• Increased rep productivity and faster ramp

Additional context

• Player-coach role with limited team support
• High ownership and visibility across the business
• Opportunity to build an AI-enabled revenue operating system from the ground up

What is it like to work at Paper? You will:

• Be joining a remote-first company with a collaborative, mission-driven culture working together to write the next chapter of Paper!
• Have opportunities to connect in person throughout the year, even while working remotely day-to-day.
• Be part of an exciting new era of growth, with fresh leadership, a bold product vision, and a redefined charter.
• Thrive in a fast-moving, build-from-scratch environment where agility and critical thinking guide decisions, collaboration is built on trust and healthy challenge, and every team member takes ownership to deliver real customer impact and grow every day.

Additional benefits:

• Comprehensive & competitive compensation, health benefits, retirement plan, stock options, and more.
• In addition to vacation days, we provide Paperites with sick days and 4 extra weeks off - including statutory holidays, Paper Days throughout the year, and a full Paper Week from Dec 25 to Jan 1.
• A $500 stipend to set-up your workspace and $100 monthly stipends to support with on-going workspace needs.
• We support growing families with generous paid parental leave.
• Unlimited access to tutoring and educational support for children of Paper employees.

You'll be joining a team of mission-driven builders who care deeply about equity in education, and who thrive in a culture of ownership, velocity, and continuous learning. If you're energized by challenges, inspired by impact, and ready to help lead a high-growth business through its next phase, we'd love to meet you.

We believe diverse teams build better products and we are committed to creating an inclusive environment for all employees. Paper does not discriminate on the basis of race, color, religion, gender, gender orientation, gender expression, sexual orientation, age, national origin, disability, marital status, or military status.

The pay range for this role is:

155,000 - 180,000 USD per year (United States)

167,000 - 198,000 CAD per year (Canada)