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
- Scale internal operations without linear headcount growth

Key Responsibilities

1. Own Net Revenue Retention (NRR)

Drive strategy across:

- Churn reduction
- Expansion (upsell, cross-sell)

Build AI-enhanced forecasting models for:

- Churn risk
- Expansion propensity

Establish clear ownership across CSMs, AMs, and lifecycle stages

- Drive AI-Powered Adoption & Time-to-Value

Ensure customers adopt:

- Core ITSM capabilities
- Spaces (current interface)
- SysAid’s agentic AI capabilities

Partner with Product & PS to:

- Embed AI into onboarding journeys (e.g., AI-generated onboarding plans)
- Deliver guided, automated adoption experiences
- Operationalize AI-driven health scoring and next-best actions

- Build a Scalable, AI-Driven Growth Engine

Design a structured expansion motion powered by AI:

- Identify expansion signals automatically (usage, gaps, triggers)

Use AI to generate:

- Deal insights
- Business cases
- Pricing recommendations

Equip teams with AI copilots for:

- Account planning
- QBR preparation
- Executive storytelling

Shift from reactive selling to predictive, insight-led growth

- Reduce Churn Through Proactive, Automated Risk Management

Build AI agents to:

- Continuously monitor customer health
- Detect risk patterns (product usage, support friction, sentiment)




- Trigger automated or human-led interventions

Move from Reactive service tickets to Predictive, system-driven retention plays

Identify systemic churn drivers (e.g., Spaces gaps, onboarding issues) and close the loop with Product

- Lead Agentic AI Transformation (Internal + Customer-Facing)

Customer-Facing AI

Define how customers should use SysAid’s agentic AI to:

- Automate IT workflows
- Improve service delivery
- Increase ROI from the platform

Partner with Product to:

- Package AI use cases into clear value propositions
- Define "when to use an agent" vs traditional workflows/integrations
- Ensure CSMs can articulate and drive adoption of AI outcomes - not just features

Internal AI & Automation

Deploy AI agents to transform post-sales operations:

- Automated QBR generation
- Call summaries and action tracking
- Ticket clustering and root cause analysis
- Renewal and expansion insights

Increase coverage per CSM through automation and AI augmentation

Redesign workflows to minimize manual work and maximize customer-facing time

- Elevate Customer Experience Through Intelligent Feedback Loops

Use AI to:

- Aggregate and cluster customer feedback (support tickets, calls, surveys)
- Identify product and experience trends at scale
- Reduce noise from service records and surface true systemic issues
- Create structured, data-backed feedback loops into Product (especially for Spaces)

- Redefine Roles for an AI-First Organization

Evolve team responsibilities:

- CSMs Outcome Orchestrators
- AMs Growth Strategists
- Support AI Supervisors

Train teams to:

- Leverage AI in daily workflows
- Interpret AI-generated insights




- Focus on high-value, human interactions

- Build & Lead a High-Performing, AI-Native Team

Define segmentation and coverage models enhanced by AI

Establish KPIs across:

- Retention & expansion
- Adoption (including AI feature adoption)
- Operational efficiency (automation rates, productivity)

Hire and develop talent comfortable operating in an AI-augmented setting

Key Success Metrics

- Net Revenue Retention (NRR)
- Gross Churn Rate
- Expansion Revenue
- Adoption of:
- Core platform (including Spaces)
- Agentic AI capabilities

- Time-to-Value
- Customer Health Score Accuracy
- % of workflows automated (internal & customer-facing)
- CSM productivity (accounts per CSM, time spent on strategic vs manual work)

Requirements

Experience

- 10+ years in SaaS Customer Success, Account Management, or Growth, and 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

Capabilities

- Strong understanding of SaaS retention mechanics (NRR drivers)
- Customer lifecycle design
- AI/automation use cases in post-sales
- Ability to translate AI capabilities into customer business value
- Data-driven and systems thinker

Leadership Traits

- Commercially oriented (growth mindset)
- Comfortable leading through product and platform transitions
- Balances strategic thinking with operational execution
- Strong cross-functional influencer (Product, Sales, Engineering)

Why This Role Matters

SysAid is at a pivotal moment:

- Transitioning platform (Spaces)
- Expanding AI capabilities
- Significant untapped growth in the installed base

This role will define how SysAid:

- Scales Customer Success with AI (without linear cost growth)
- Differentiates through intelligent, automated customer experiences
- Turns AI into a core driver of retention and expansion

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📌 Director, Customer Retention & Growth (Americas) (Toronto)
🏢 Socket.dev
📍 Toronto