Director of Revenue Operations, Paper
CA$155-180k
$167,000 - $198,000 CAD, plus equity
Tutoring, enrichment, college & career support for K-12
Be an early applicant
Tutoring, enrichment, college & career support for K-12
501-1000 employees
Be an early applicant
CA$155-180k
$167,000 - $198,000 CAD, plus equity
501-1000 employees
Company mission
To ensure equal access to academic support for all students—no matter their circumstances.
Role
Who you are
- 6 to 10 years in RevOps, Sales Ops, or GTM strategy
- Experience in a high-growth SaaS or tech company (Series A to C)
- Strong CRM expertise (Salesforce preferred), with hands-on experience configuring
- Experience implementing or leveraging AI tools in GTM workflows
- Analytical, with ability to translate data into action
- Comfortable operating as both strategist and executor
What the job involves
- 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
- 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
- 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
Our take
The education sector struggles to provide equitable, accessible learning support, especially for underserved students., Many learners face challenges due to limited resources, creating achievement gaps that desperately need targeting.
Paper is tackling this issue with 24/7 personalised tutoring through its GROW program. By offering interactive tools, career exploration, and post-secondary planning, Paper now supports over 3M students in building the skills they need for academic success.
The company had a turbulent 2024, marked by leadership changes and layoffs. However, it is turning a corner, with the recent appointment of a new CEO, the company is ready to stabilise and rebuild, positioning itself for growth once again.
Steph
Company Specialist at Welcome to the Jungle
Insights
132% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Jul 2022
$26.3m
SERIES B
Jan 2022
$25.9m
SERIES B
Total funding: $65.3m
Company HQ
Milton Parc, Montreal, QC
Leadership
Martina Tam
(CEO)Previously co-founded OneRadiant where they served as the CEO. They also worked in VP roles at brightwheel and MasterClass and as a Senior Director at Eventbrite.
Share this job
View 4 more jobs at Paper