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 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)
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
