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
Scale internal operations without linear headcount growth
Key Responsibilities
1. Own Net Revenue Retention (NRR)
Churn reduction
Build AI-enhanced forecasting models for
Expanpropensitypensi
Establish clear ownership across CSMs, AMs, and lifecycle stages
2. Drive AI-Powered Adoption & Time-to-Value
Spaces (ninterfacefac
SysAid’s agentic capabilities
Partner with Product & PS
Embed AI into onboarding journeys (e.g., AI-generated onboarding plan
Deliver guided, automated adoption experiences
es Operationalize AI-driven health scoring and next-best action
3. Build a Scalable, AI-Driven Growth Engine
Design a structured expansion motion powered by AI
Identify expansion signals automatically (usage, gaps, trigger
Use AI to generate
Deal insights
Businesses cases
Pricing recommendations
Equip teams with AI copilots
QBR preparation
Executive storytelling
Shift from reactive selling to predictive, insight-led growth
4. Reduce Churn Through Proactive, Automated Risk Management
Buil d AI agents
Continuously monitor customer health




Trigger automated or human-led intervention
Move from: Reactive service tickets → to Predictive, system-driven retention pla Identify systemic churn drivers (e.g., Spaces gaps, onboarding issues) and close the loop with Produt
5. Lead Agentic AI Transformation (Internal + Customer-Facing)
Define how customers should use SysAid’s agentic AI t
to automate workflows
Increase ROI from the platform
Partner with Product to
Package AI use cases into clear value propositions
Defin e “when to use an agent” vs traditional workflows/integratioEnsuree CSMs can articulate and drive adoption of AI outcomes, not just featur
Internal AI & Automati
Deploy AI agents to transform post-sales operations:
Automated QBR generation, call summaries,s and action tracking
Ticket clustering and root cause analysis
Renewal and expansion insights
Increas e coverage per CSM through automation and AI augmentation
Redesign workflows to minimize manual work and maximize customer-facing time
6. Elevate Customer Experience Through Intelligent Feedback Loop
Use AI to
Aggregate and cluster customer feedback (support tickets, calls, surveys)y
Identify product and experience trends at scale
Reduce noise from service records and surface true system issues
Create structured, data-backed feedback loops into Product (especially for Space
7. Redefine Roles for an AI-First Organization: Evolve team responsibilities
Train teams




Leverage AI in daily workflows
Interpret AI-generated insights
Focus on high-value, human interaction
8. Build & Lead a High-Performing, AI-Native Te
Define segmentation and coverage models enhanced by
Retention & expansi
Operational efficiency (automation rates, productivity
Hire and develop talent comfortable operating in an AI-augmented workplace
Key Success Metrics
Net Revenue Retention (NRR)
Gross Churn Ra
Expansion Reven
Agentic AI capabilities
Time-to-Val
Customer Health Score Accuracy
of workflows automated (internal & customer-facing)
CSM productivity (accounts per CSM, time spent on strategic vs manual work)
Experiens
10+ years in SaaS Customer Success, Account Management, or Growth, and at least 5 years in manarolesr ro
Proven ownership of retention and expansion targ
Experience leading AI/automation initiatives in customer-facing teams
Background in ITSM, enterprise SaaS, or workflow platforms preferred
Capabilits
of SaaS retention mechanics (NRR drive)
signAI/automation use cases in post-
Ability to translate AI capabilities into customer business
Data-driven and systems thinking
Leadership
Commercially oriented (growth min
mindset). Comfortable leading through product and platform transi
Balances strategic thinking with operational exec
Strong cross-functional influencer (Product, Sales, Engineering)
Why This Role Matters
Expanding AI capa
lities Significant untapped growth in the installed
This role will define how SysAid:
SysAid: Scales Customer Success with AI (without linear cost g
Differentiates through intelligent, automated customer exper
Turns AI into a core driver of retention

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📌 Director, Customer Retention & Growth (Americas) (Ontario)
🏢 SysAid
📍 Ontario