Senior Director, Customer Retention & Growth (Americas)

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

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

• Ensure customers adopt:
• Core ITSM capabilities
• Spaces (new 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

3. 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

4. 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

5. 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

6. 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)

7. 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

8. 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 environment

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)

Experience

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