Hybrid Director of Revenue Operations

at Rightsline

• Job title: Director of Revenue Operations
• Job type: Full Time
• Experience level: Lead
• Salary: Not specified
• Degree requirement: Bachelor's Degree
• Tech skills: Tableau
• Location requirements: Hybrid, Toronto, Canada

About the role

• Director of Revenue Operations at Rightsline leading B2B revenue strategies and operations across Sales and Marketing. Ensuring cross-functional alignment and driving growth in a hybrid environment.

Responsibilities

• Partner with executive leadership to develop the long-term revenue strategy and execution (top-down and bottom-up).
• Drive cross-functional alignment of goals, processes, and metrics across Marketing, Sales, and Customer Success, establishing SLAs and Rules of Engagement for the customer journey.
• Design the territory structure, including market segmentation, territory management (with TAM/SAM/SOM analysis), Sales organization planning, and Pricing & Packaging initiatives.
• Manage Incentive Compensation, including developing commission plan structures, quota assignments, and facilitating commission calculations in partnership with Finance.
• Own the revenue forecasting process and define/manage Key Performance Indicators (KPIs), providing actionable insights via executive dashboards.
• Design, document, and implement optimized end-to-end revenue processes (lead-to-cash/renewal), identifying and fixing bottlenecks to drive organizational productivity.
• Own the entire RevOps technology stack (CRM, CPQ, Marketing Automation, etc.), ensuring data quality, integration, and supporting ongoing operations and new initiatives.

Requirements

• 10+ years of progressive experience (minimum 7 years) in Revenue Operations, Sales Operations, or related functions in fast-paced B2B/SaaS environments, with 5+ years in leadership managing high-performing teams.
• Bachelor’s degree in Business, Finance, or related field; MBA is a plus.
• Proven experience building and scaling RevOps functions, ideally from $20M to $100M+ growth stages.
• Deep expertise in modern B2B go-to-market motions, managing a range of deal sizes ($25K ARR to $1M+ enterprise).
• Track record of improving operational efficiency and driving measurable business impact.
• Experience in Mergers & Acquisitions (M&A), from due diligence to synergy execution, is highly desirable.
• Strong command of RevOps technology stacks, including CRM (e.g., Salesforce), CPQ, and Marketing Automation, and expertise in data analysis, financial modeling, and BI tools (Tableau, Power BI).
• Prior experience in Sales Management and/or Customer Success is advantageous.
• Strategic thinker and action-oriented self-starter with the ability to prioritize high-impact initiatives.
• Excellent communication, presentation, and cross-functional leadership skills, with a proven ability to influence stakeholders at all levels.

Benefits

• Competitive Compensation and Health & Dental Benefits
• 401K / RRSP Match Program
• Flexible work hours
• Birthdays off
• One-time home office allowance
• Unlimited vacation time
• Team socials
• Happy hours
• Career progression in a high growth environment