Director of Revenue Operations

SysAid Technologies•Toronto, ON

About The Position

SysAid’s mission is to liberate organizations by putting AI to work for them and their people. Our vision is to be a leading, innovative AI Service Management platform for organizations, transforming employee experience and productivity. We are a high-growth SaaS company selling IT Service Management, a space that is being propelled into rapid growth as businesses worldwide accelerate their digital transformation. SysAid is recognized in the Gartner Magic Quadrant for ITSM and is the mid-tier industry leader in Gartner Peer Insights. AWS awarded us the Rising ISV Star Award. We have over 4,000 customers in 140 countries, and our software impacts the daily working lives of over 9 million end users. We are looking for a Director of Revenue Operations to architect, lead, and scale the operating system that powers SysAid’s revenue engine. In this strategic leadership role, you will own the end-to-end Revenue operations and optimization function across Sales, Marketing, Account Management, Customer Success, Channels, and Deal Desk. Reporting to our CFO, you will translate strategy into predictable, scalable execution by designing best practice operational practices and driving excellence through constant and systematic optimization of the best execution for every stage in the GTM funnel. SysAid is an aggressive, emerging brand in the Enterprise ITSM space, and we need a hands-on leader who naturally leverages the power of AI to scale our GTM motion with rigor, increase pipeline conversion, drive forecast accuracy, and turn data into a true competitive advantage.

Requirements

7+ years of progressive RevOps, Sales Ops, or Business Ops experience in B2B SaaS.
3+ years of experience in a leadership role (Director or Head of level), building and scaling a RevOps function in a high-growth environment.
Deep, hands-on expertise with Salesforce and the broader GTM tech stack (e.g., Salesloft, Gong, DealHub).
Experience with AI functionality within RevOps and exposure to global, multi-region GTM motions (indirect/channel sales experience is a plus).
Demonstrated ability to operationalize proven sales methodologies and system-based selling.
Strong analytical foundation with an ultra-high level of personal accountability for data quality and GTM execution.
Direct experience partnering with executive leadership on forecasting, GTM planning and pricing.
Excellent communication skills, executive presence, and the ability to drive cross-functional alignment.

Nice To Haves

indirect/channel sales experience is a plus

Responsibilities

End-to-End RevOps Leadership: Own and optimize revenue operations across Sales, Account Management, Customer Success, Channels, and Deal Desk.
Process Optimization: Optimize Quote-to-Cash and Deal Desk workflows, including pricing approvals and contract management, in partnership with Finance and Legal.
Program Management: Design and implement programs that continuously improve pipeline analytics and revenue KPIs across the funnel.
Data Governance & Cleaning: Architect cross-functional workflows to eliminate missing opportunity data and standardize loss/closed definitions across direct sales and partner overlays.
Lifecycle Analytics Optimization: Partner with Product Marketing and Customer Revenue teams to instrument product experience analytics directly into Salesforce and Gainsight, eliminating technical gaps in post-trial conversion metrics.
Sales Methodology Enablement: Partner with Sales Enablement to translate the SysAid Sales Methodology into systems, stages, exit criteria, and coaching dashboards.
Team Management: Build, train and develop a high-performing RevOps team composed of AI agents and human capital.
GTM Planning: Partner with Finance to architect and run annual and quarterly planning cycles, including segmentation, territories, quotas, headcount, and capacity modeling.
Systems Strategy: Lead the Salesforce and broader business applications strategy, integrating marketing automation, CS platforms, and finance tools into a unified data backbone.
Leadership Cadence: Design and operate forecast calls, pipeline reviews, QBRs, and board preparation.