SysAid

Senior Director, Customer Retention & Growth (Americas)

SysAid • $130K — $180K *
Toronto, ON M3C 0E3Hybrid
Information Technology
8 - 10 years of experience
3 weeks ago
Job Overview by Ladders

Qualifications

  • 10+ years in SaaS Customer Success, Account Management or Growth; 5 years in management roles
  • Proven ownership of retention and expansion targets
  • Experience leading AI/automation initiatives in customer-facing teams
  • Background in ITSM, enterprise SaaS, or workflow platforms preferred
  • Strong understanding of SaaS retention mechanics (NRR drivers)
  • Ability to translate AI capabilities into customer business value
  • Commercially oriented with a growth mindset

Responsibilities

  • Own and strategize for Net Revenue Retention (NRR)
  • Drive AI-powered adoption and time-to-value for customers
  • Build a scalable, AI-driven growth engine
  • Reduce churn through proactive, automated risk management
  • Lead the agentic AI transformation internally and for customers
  • Elevate customer experience through intelligent feedback loops
  • Redefine team roles for an AI-first organization
  • Build and lead a high-performing, AI-native team

Benefits

  • Opportunity to define and shape AI-augmented customer success initiatives
  • Work in a pivotal role during SysAid's transition to a new platform and expanded AI capabilities
  • Engage in a unique challenge of scaling Customer Success without linear cost growth
  • Access to continuous professional development in AI and customer relations
  • Join a forward-thinking, technology-driven organization focused on innovation and growth
Full Job Description
Description

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)


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

About SysAid

SysAid Technologies Ltd. is a leading provider of IT service management (ITSM) solutions that enable IT professionals to manage their IT infrastructures and services with greater ease and efficiency. The company's flagship product, SysAid, is a comprehensive ITSM solution that provides help desk automation, asset management, and advanced reporting and analytics. SysAid is used by thousands of organizations worldwide, including small and medium-sized businesses, government agencies, and Fortune 500 companies. The company was founded in 2002 and is headquartered in Tel Aviv, Israel.
Learn more about SysAid
Size
500 employees
Industry
Information Technology
Founded
2002
* Ladders Estimates

Similar Jobs

Ad banner background

Get Ready For Your
Next Interview

More Jobs at SysAid

More Information Technology Jobs

Find similar Senior Director, Customer Retention & Growth (Americas) jobs:

NationwideToronto, ON