Senior Director, Customer Retention & Growth (Americas)

SysAid • $150K — $180K *

Toronto, ON M3C 0E3Hybrid

Information Technology

8 - 10 years of experience

Reposted 1 month 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

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Full Job Description

Description

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

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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

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