Director, Customer Retention & Growth (Americas)

SysAid; Toronto; On-site; CAD 180,000 - 230,000; Full time

Job summary

SysAid is seeking a Senior Director of Customer Retention & Growth to own net revenue retention and transform post-sales into an AI-enabled growth engine. You will lead the AI-powered adoption, health scoring, and expansion strategies across CS, AM, and lifecycle stages.

The role requires 10+ years in SaaS CS/AM or Growth with 5+ years in leadership, plus experience driving AI/automation in customer-facing teams. Join SysAid to redefine retention through predictive insights.

Qualifications

• 10+ years in SaaS Customer Success, Account Management, or Growth.
• At least 5 years in management roles.
• Experience leading AI/automation initiatives in customer-facing teams.
• Background in ITSM, enterprise SaaS, or workflow platforms preferred.

Responsibilities

• Own Net Revenue Retention (NRR) and churn reduction.
• Build AI-enhanced forecasting models for CS, AM, and lifecycle stages.
• Scale expansion with AI-driven signals and playbooks.
• Embed AI into onboarding journeys and adoption experiences.
• Lead a scalable, AI-driven growth engine for expansion and pricing insights.
• Develop proactive risk management with AI agents and health monitoring.
• Oversee internal AI transformation across post-sales operations.
• Collaborate with Product, PS, and Sales to maximize AI ROI.
• Define roles and training for an AI-first organization.

Skills

SaaS Growth

CS/AM Leadership

AI & Automation

Cross-functional Leadership

ITSM Familiarity

Tools

Spaces & SAI

Forecasting Tools

Job description

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


• Scale internal operations without linear headcount growth

Key Responsibilities

1. Own Net Revenue Retention (NRR)

• Churn reduction


• Build AI-enhanced forecasting models for


• Expanpropensitypensi


• Establish clear ownership across CSMs, AMs, and lifecycle stages

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

• Spaces (ninterfacefac


• SysAid’s agentic capabilities


• Partner with Product & PS


• Embed AI into onboarding journeys (e.g., AI-generated onboarding plan


• Deliver guided, automated adoption experiences


• es Operationalize AI-driven health scoring and next-best action

3. Build a Scalable, AI-Driven Growth Engine

• Design a structured expansion motion powered by AI


• Identify expansion signals automatically (usage, gaps, trigger


• Use AI to generate


• Deal insights


• Businesses cases


• Pricing recommendations


• Equip teams with AI copilots


• QBR preparation


• Executive storytelling


• Shift from reactive selling to predictive, insight-led growth

4. Reduce Churn Through Proactive, Automated Risk Management

• Build AI agents


• Continuously monitor customer health


• Trigger automated or human-led intervention


• Move from: Reactive service tickets to Predictive, system-driven retention pla Identify systemic churn drivers (e.g., Spaces gaps, onboarding issues) and close the loop with Produt

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

• Define how customers should use SysAid’s agentic AI t


• to automate workflows


• 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/integratioEnsuree CSMs can articulate and drive adoption of AI outcomes, not just featur

Internal AI & Automati

• Deploy AI agents to transform post-sales operations:


• Automated QBR generation, call summaries,s 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 Loop

• Use AI to


• Aggregate and cluster customer feedback (support tickets, calls, surveys)y


• Identify product and experience trends at scale


• Reduce noise from service records and surface true system issues


• Create structured, data-backed feedback loops into Product (especially for Space

7. Redefine Roles for an AI-First Organization: Evolve team responsibilities

• Train teams


• Leverage AI in daily workflows


• Interpret AI-generated insights


• Focus on high-value, human interaction

8. Build & Lead a High-Performing, AI-Native Te

• Define segmentation and coverage models enhanced by


• Retention & expansi


• 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 Ra


• Expansion Reven


• Agentic AI capabilities


• Time-to-Val


• Customer Health Score Accuracy


• of workflows automated (internal & customer-facing)


• CSM productivity (accounts per CSM, time spent on strategic vs manual work)

Experiens

• 10+ years in SaaS Customer Success, Account Management, or Growth, and at least 5 years in manarolesr ro


• Proven ownership of retention and expansion targ


• Experience leading AI/automation initiatives in customer-facing teams


• Background in ITSM, enterprise SaaS, or workflow platforms preferred

Capabilits

• of SaaS retention mechanics (NRR drive)


• signAI/automation use cases in post-


• Ability to translate AI capabilities into customer business


• Data-driven and systems thinking

Leadership

• Commercially oriented (growth min


• mindset). Comfortable leading through product and platform transi


• Balances strategic thinking with operational exec


• Strong cross-functional influencer (Product, Sales, Engineering)

Why This Role Matters

• Expanding AI capa


• lities Significant untapped growth in the installed

This role will define how SysAid:

• SysAid: Scales Customer Success with AI (without linear cost g


• Differentiates through intelligent, automated customer exper


• Turns AI into a core driver of retention