VP of Sales, Customer Success & Growth, North America

SysAid Technologies•Toronto, ON

9d•Hybrid

About The Position

SysAid is looking for a VP of Sales, Customer Success & Growth to lead our North America go-to-market organization, which includes roughly 25 professionals spanning New Logo Acquisition, Customer Success, and Expansion/Growth. This is a full revenue lifecycle leadership role—you will own new business, retention, and expansion, and you will be accountable for the health, forecast, and growth of the entire North American book of business. You will manage a team of function leaders, working hand-in-hand with them to set targets, build and inspect the pipeline, and keep the business forecast accurate and on track. Reporting to the CRO, you will partner closely with our UK & Rest of World commercial leader and our Channel Leader to align global GTM strategy, share best practices, and drive consistent execution across regions.

Requirements

10+ years of progressive GTM leadership experience with direct P&L ownership across sales, customer success, and/or expansion, ideally in B2B SaaS or enterprise software.
Proven experience managing Senior Directors or equivalent leaders, not just individual contributors.
A strong track record of expanding pipeline coverage, improving win rates, growing average deal size, and shortening sales cycles.
Demonstrated success driving retention, reducing churn, and growing expansion revenue within an existing customer base.
Deep experience building or running risk-scoring processes that leadership and the board can rely on.
Experience presenting commercial performance and growth metrics to executive leadership and boards.
Prior experience in cybersecurity, ITSM, or adjacent enterprise IT software is a plus.

Responsibilities

Own the P&L: Manage the North America P&L across new logo acquisition, customer success, and expansion for a team of roughly 25 professionals.
Team Leadership: Hire, coach, and manage a team of Senior Directors, providing the resources and air cover needed to hit their targets.
Forecast Accuracy: Build and maintain an accurate, defensible forecast; run consistent pipeline and forecast cadences (weekly pipeline reviews, MBRs, quarterly planning).
Drive Acquisition: Partner with the Senior Director of Sales to drive net-new logo growth, optimizing pipeline generation, win rates, and sales cycle velocity.
Maximize Retention: Own gross revenue retention outcomes alongside the Senior Director of Customer Success, focusing on proactive risk scoring and churn mitigation.
Accelerate Expansion: Drive net revenue expansion with the Senior Director of Growth by leading upsell, cross-sell, and account growth motions.
Optimize Operations: Design and evolve the NA operating model, including territory segmentation, quota setting, and compensation design.
Executive Alignment: Represent North American performance, retention metrics, and growth strategy to executive leadership and the board.