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

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

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

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

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

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

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, 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