Senior Director, Customer Retention & Growth (Americas)

SysAid Technologies•Toronto, ON

10d

About The Position

SysAid is a leading IT Service Management (ITSM) platform helping organizations deliver exceptional service experiences. As the platform evolves with innovations like Spaces and SAI, SysAid is redefining how IT teams operate and how customers realize value. The company is in a critical phase where AI is a growth driver for both customers and the internal operating model. This role seeks a Senior Director of Customer Retention & Growth to own SysAid’s net revenue retention (NRR) and lead the transformation of the 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
Proven ownership of retention and expansion targets
Strong understanding of SaaS retention mechanics (NRR drivers)
Strong understanding of 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 (strong plus)
Background in ITSM, enterprise SaaS, or workflow platforms preferred

Responsibilities

Own Net Revenue Retention (NRR) including driving strategy across churn reduction and expansion (upsell, cross-sell), building AI-enhanced forecasting models for churn risk and expansion propensity, and establishing clear ownership across CSMs, AMs, and lifecycle stages.
Drive AI-Powered Adoption & Time-to-Value by ensuring customers adopt core ITSM capabilities, Spaces (new interface), and SysAid’s agentic AI capabilities, and partnering 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 to identify expansion signals automatically and use AI to generate deal insights, business cases, and pricing recommendations, equipping teams with AI copilots for account planning, QBR preparation, and executive storytelling, and 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, moving from reactive service tickets to predictive, system-driven retention plays, and identifying systemic churn drivers to 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 from the platform, partnering with Product to package AI use cases into clear value propositions and define agent usage, ensuring CSMs can articulate and drive adoption of AI outcomes, deploying AI agents to transform post-sales operations (automated QBR generation, call summaries, ticket clustering, renewal/expansion insights), increasing coverage per CSM through automation and AI augmentation, and redesigning workflows to minimize manual work.
Elevate Customer Experience Through Intelligent Feedback Loops by using AI to aggregate and cluster customer feedback, identify product and experience trends at scale, reduce noise from service records, and create structured, data-backed feedback loops into Product.
Redefine Roles for an AI-First Organization by evolving team responsibilities (CSMs to Outcome Orchestrators, AMs to Growth Strategists, Support to AI Supervisors) and training 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 (including AI feature adoption), and operational efficiency, and hiring and developing talent comfortable operating in an AI-augmented environment.

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