Director of Revenue Operations (AI)

Location: Remote in Canada or the United States; applicants must be able to live and work full-time in one of these countries. Some roles may require proximity to offices in Toronto, Calgary, or Vancouver.

Company

Provides software that helps legal, finance, and tax teams manage business entities and corporate structures for transaction, audit, governance, tax, and compliance readiness.

What you will do

• Operationalize the revenue strategy by translating business objectives into revenue targets, capacity models, headcount plans, and measurable operating cadences.
• Own revenue forecasting, KPI development, pipeline rigor, and risk identification in partnership with Finance, with particular attention to Customer Experience forecasting.
• Coordinate Sales, Marketing, Customer Experience, and Product through shared definitions, SLAs, conversion metrics, accountability frameworks, and quarterly business reviews.
• Oversee lead qualification, deal attribution, SKU management, pipeline hygiene, pricing and packaging alignment, and demand-generation automation.
• Set the architectural direction for the HubSpot ecosystem and guide the transition toward AI-enabled CRM hygiene, lead routing, predictive workflows, and administrative automation.
• Manage and mentor the RevOps Analyst while building a scalable, high-performing RevOps function.

Requirements

• 7+ years of experience in high-growth Revenue Operations, GTM Strategy, or Sales Operations, including prior people management.
• Essential experience in B2B SaaS and expert knowledge of ARR, LTV/CAC, churn, pipeline velocity, and incentive design.
• Proven ability to influence C-suite and board-level decisions with data-backed insights and communicate complex information to non-technical audiences.
• Experience architecting and piloting AI-driven workflows, including agentic automation, predictive lead scoring, or AI-assisted CRM hygiene.
• Deep familiarity with CRM ecosystems; HubSpot experience is strongly preferred, along with the ability to evaluate architecture and consultant recommendations.
• Strategic, pragmatic, tool-agnostic leadership with the ability to drive outcomes through influence rather than authority.

Culture & Benefits

• Remote-first work environment based on trust, autonomy, accountability, and distributed collaboration.
• Culture focused on outcome-driven work, wide responsibility, continuous learning, and strategic speed.
• At least three weeks of vacation, five sick days, personal/flex days, and a company-wide winter holiday shutdown.
• Health, dental, vision, long-term disability coverage, and a Health Spending Account.
• Flexible parental leave with top-ups and a dedicated work-from-home allowance.