Senior Director, Customer Retention & Growth (Americas)

SysAid Technologies•Toronto, ON

About The Position

SysAid is a leading IT Service Management (ITSM) platform helping organizations deliver exceptional service experiences. As we evolve our platform with innovations like Spaces and SAI, we are redefining how IT teams operate—and how customers realize value. We are entering a critical phase where AI is not just a feature—but a growth driver, both for our customers and our internal operating model. We are seeking a Senior Director of Customer Retention & Growth to own SysAid’s net revenue retention (NRR) and lead the transformation of our post-sales organization into an AI-enabled, insight-driven growth engine. This leader will harness agentic AI to help customers achieve faster, measurable outcomes, drive proactive, data-driven engagement, and scale internal operations without linear headcount growth.

Requirements

10+ years in SaaS Customer Success, Account Management, or Growth.
At least 5 years in manager roles.
Proven ownership of retention and expansion targets.
Experience leading AI/automation initiatives in customer-facing teams (strong plus).
Background in ITSM, enterprise SaaS, or workflow platforms preferred.
Strong understanding of SaaS retention mechanics (NRR drivers) and customer lifecycle design.
Strong understanding of AI/automation use cases in post-sales.
Ability to translate AI capabilities into customer business value.
Data-driven and systems thinker.
Commercially oriented (growth mindset).
Comfortable leading through product and platform transitions.
Balances strategic thinking with operational execution.
Strong cross-functional influencer (Product, Sales, Engineering).

Nice To Haves

Experience leading AI/automation initiatives in customer-facing teams.

Responsibilities

Own Net Revenue Retention (NRR) by driving strategy across churn reduction and expansion (upsell, cross-sell).
Build AI-enhanced forecasting models for churn risk and expansion propensity.
Establish clear ownership across CSMs, AMs, and lifecycle stages.
Drive AI-Powered Adoption & Time-to-Value by ensuring customers adopt core ITSM capabilities, Spaces, and SysAid’s agentic AI capabilities.
Partner with Product & PS to embed AI into onboarding journeys, deliver guided, automated adoption experiences, and operationalize AI-driven health scoring and next-best actions.
Build a Scalable, AI-Driven Growth Engine by designing a structured expansion motion powered by AI, identifying expansion signals automatically, and using AI to generate deal insights, business cases, and pricing recommendations.
Equip teams with AI copilots for account planning, QBR preparation, and executive storytelling, shifting from reactive selling to predictive, insight-led growth.
Reduce Churn Through Proactive, Automated Risk Management by building AI agents to continuously monitor customer health, detect risk patterns, and trigger automated or human-led interventions.
Move from reactive service tickets to predictive, system-driven retention plays.
Identify systemic churn drivers and close the loop with Product.
Lead Agentic AI Transformation (Internal + Customer-Facing) by defining how customers should use SysAid’s agentic AI to automate IT workflows, improve service delivery, and increase ROI.
Partner with Product to package AI use cases into clear value propositions and define when to use an agent vs traditional workflows/integrations.
Ensure CSMs can articulate and drive adoption of AI outcomes—not just features.
Deploy AI agents to transform post-sales operations, including automated QBR generation, call summaries, ticket clustering, renewal and expansion insights.
Increase coverage per CSM through automation and AI augmentation, and redesign workflows to minimize manual work and maximize customer-facing time.
Elevate Customer Experience Through Intelligent Feedback Loops by using AI to aggregate and cluster customer feedback, identify product and experience trends at scale, and reduce noise from service records.
Create structured, data-backed feedback loops into Product.
Redefine Roles for an AI-First Organization by evolving team responsibilities (CSMs → Outcome Orchestrators, AMs → Growth Strategists, Support → AI Supervisors).
Train teams to leverage AI in daily workflows, interpret AI-generated insights, and focus on high-value, human interactions.
Build & Lead a High-Performing, AI-Native Team by defining segmentation and coverage models enhanced by AI, establishing KPIs across retention, expansion, adoption, and operational efficiency.
Hire and develop talent comfortable operating in an AI-augmented environment.