VP of Sales, Customer Success & Growth, North America

Location: Toronto, Ontario, Canada (Hybrid: 4 days in-office, 1 day remote)

Territory: North America

Reports to: Chief Revenue Officer

Target Start: August 2026

Compensation: OTE (70% Base Salary, 30% Commission) + Benefits

About SysAid

SysAid is a dynamic SaaS company specializing in IT Service Management while pioneering generative and conversational AI. Recognized as a leading innovator in the industry, we are featured in the Gartner Magic Quadrant for ITSM and honored with AWS's prestigious Rising ISV Star Award. With over 4,000 clients across 140 countries and a daily impact on over 9 million end-users, we are committed to transforming the ITSM landscape.

The Role

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.

Who You Are

• Results-Driven: You are highly motivated by hitting targets, taking deep ownership of regional performance and holding yourself accountable to ambitious goals.
• Leader of Leaders: You excel at managing Senior Directors—coaching, challenging, and holding them to a high bar while giving them the autonomy to run their functions.
• Deeply Accountable: Accountability is your default setting. You own the forecast, the miss, and the fix, rather than passing problems up or sideways.
• Commercially Rigorous: You demand highly accurate forecasting, preferring to surface risks early rather than explain them away later.
• Builder and Strategist: Energized by designing the operating model, you are comfortable setting regional strategy while remaining willing to dive into the details of a stuck deal or at-risk renewal.
• Cross-Functional Unifier: You build trust quickly across functions and levels, aligning Sales, CS, and Growth leaders into a single cohesive team rather than managing competing agendas.

What You'll Do

• 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.

• Extensive Experience: 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.
• Manager of Managers: Proven experience managing Senior Directors or equivalent leaders, not just individual contributors.
• Scaling Success: A strong track record of expanding pipeline coverage, improving win rates, growing average deal size, and shortening sales cycles.
• Customer Lifecycle Expertise: Demonstrated success driving retention, reducing churn, and growing expansion revenue within an existing customer base.
• Forecasting Discipline: Deep experience building or running risk-scoring processes that leadership and the board can rely on.
• Executive Presence: Experience presenting commercial performance and growth metrics to executive leadership and boards.
• Industry Knowledge: Prior experience in cybersecurity, ITSM, or adjacent enterprise IT software is a plus.

Why Join SysAid

You'll lead one of SysAid's largest and most strategic regional GTM organizations, with full ownership of the revenue lifecycle rather than a single slice of it. You'll partner directly with executive leadership and your global counterparts to shape how SysAid grows, at a company where AI is rapidly reshaping both the product and how our go-to-market team operates.

Benefits & Perks

• Stock options, matched RRSP, health & Dental Plan coverage
• Quarterly engagement events, summer party & holiday party

Equal Opportunity Employer

SysAid is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees