Senior Director, Revenue Intelligence & Operations

360insights•Toronto, ON

8d•CA$125,000 - CA$145,000

About The Position

The Senior Director, Revenue Intelligence & Operations is responsible for transforming, building and scaling the commercial operating model that powers the company's revenue engine. This role connects strategy to execution across Sales, Marketing, Account Management, Customer Success, Partnerships, Finance, Product, and Business Operations through the systems, processes, data, governance, and insights that drive predictable growth. The position ensures the organization can effectively move from opportunity to revenue while maintaining operational discipline, visibility, and scalability across the customer lifecycle. This is an existing vacancy. In addition to salary, we offer an annual corporate bonus, stock options, and a comprehensive benefits programme.

Requirements

10+ years of progressive Revenue Intelligence, Revenue Operations, Sales Operations, Go-to-Market Operations, Business Operations, or related leadership experience in a mid-size B2B SaaS or technology company; incentives market experience is an asset.
Proven success leading both strategy and execution across commercial operations, including operating model design, quote-to-cash process ownership, forecasting, analytics, systems transformation, and large-scale cross-functional initiatives.
Able to build, lead, and mentor high-performing teams in a fast-paced environment while fostering integrity, transparency, collaboration, curiosity, and continuous improvement.
Collaborative, influential leader who can align executives, peers, and front-line teams around disciplined commercial processes while reducing unnecessary friction and improving adoption.
Strong commercial systems fluency and experience using technology, automation, and BI tools to improve revenue visibility; experience with CRM, CPQ, Deal Desk, contracting, ERP middleware, and related tools is essential.
Exceptional financial planning, forecasting, modelling, SaaS reporting, KPI, and revenue management skills, including bookings-to-revenue and conversion models.
Strong change leadership, communication, stakeholder management, analytical, data storytelling, and strategic thinking skills.
Thrives in ambiguity and complexity, with a demonstrated ability to build structure, drive alignment, and deliver outcomes in evolving environments.

Nice To Haves

incentives market experience is an asset

Responsibilities

Lead transformation initiatives that redefine how revenue operations, systems, and go-to-market processes work as customer buying behavior, AI capabilities, and commercial technology continue to evolve.
Design and mature the Revenue Intelligence and Operations roadmap, including systems, data, governance, processes, and operating rhythms needed to scale predictably.
Lead, coach, and develop the Revenue Intelligence and Operations team, setting clear priorities, accountability, and standards for strong business partnership.
Design and govern the end-to-end commercial operating model, partnering across Sales, Marketing, Account Management, Customer Success, Partnerships, Finance, Product, and Business Operations to turn revenue insights into growth priorities across the customer lifecycle.
Provide analytical leadership for go-to-market strategy, sales planning, marketing performance, customer lifecycle improvements, and executive decision-making.
Demonstrate success challenging legacy approaches and leading transformational initiatives that materially improved commercial performance, scalability, or operating effectiveness.
Support M&A due diligence and integration, including process, systems, reporting, and data alignment.
Evaluate and continuously evolve the go-to-market operating model, identifying opportunities to improve how demand is generated, qualified, converted, retained, and expanded.
Own the design, governance, and evolution of the commercial systems ecosystem supporting the quote-to-order process, including CRM, CPQ, Deal Desk, contracting, approvals, and related integrations. Ensure systems, workflows, reporting, and data structures support scalable growth, strong adoption, and efficient execution across the revenue organization.
Simplify, automate, and standardize workflows so revenue teams capture the right data at the right point in the sales process, act faster on insights, and spend more time with customers.
Oversee Deal Desk and the sales contract process from quote configuration and approvals through negotiation, execution, order handoff, and downstream system integration, ensuring efficient approvals, compliance, and clean handoffs.
Create practical playbooks, guides, training, and adoption plans that help teams use systems and processes consistently.
Understand how data flows from opportunity creation through quote, contract, order, implementation, revenue, renewal, and expansion, and use that knowledge to improve process design, adoption, and reporting quality.
Establish standards, definitions, controls, and accountability for trusted pipeline, bookings, revenue, retention, customer health, and performance data.
Champion data accuracy across revenue systems and resolve risks that weaken reporting, forecasting, or decision-making.
Ensure upstream data quality supports downstream forecasting, reporting, customer visibility, implementation planning, revenue recognition, renewal management, and executive decision-making.
Oversee customer data migration, including mapping, cleansing, validation, governance, and adoption controls for CRM implementation and ongoing system management.
Develop territory, capacity, customer, and segment insights to align opportunities, resources, forecasts, and revenue goals.
Develop and enforce revenue and sales policies that improve consistency, compliance, and operating discipline.
Provide actionable revenue intelligence on go-to-market performance, funnel conversion, win/loss, productivity, retention, customer health, and KPIs for executive and board reporting.
Own revenue forecasting, including pipeline health, quote-to-order conversion, bookings-to-revenue conversion, renewals, churn, expansion, implementation timing, product mix, and revenue assumptions.
Identify and address process, system, and data breakdowns that reduce forecast accuracy, revenue visibility, operational efficiency, or customer lifecycle insight.
Partner with FP&A to improve forecast accuracy, variance analysis, scenario planning, and strategic decision-making.
Support incentive compensation design and own variable compensation planning, forecasting, quota maintenance, and calculations.