Senior Director, Customer Retention & Growth (Americas) at SysAid Technologies

Toronto, Ontario, Canada -

Full Time

Start Date

Immediate

Expiry Date

06 Sep, 26

Salary

0.0

Posted On

08 Jun, 26

Experience

10 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Net Revenue Retention, Churn Reduction, Customer Success Management, AI Implementation, Account Management, SaaS Growth Strategy, ITSM, Data-Driven Engagement, Customer Lifecycle Design, Cross-functional Leadership, Predictive Analytics, Operational Scaling, Executive Storytelling, Customer Health Scoring, Upselling, Cross-selling

Industry

Software Development

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 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

Responsibilities

Lead the transformation of the post-sales organization into an AI-enabled growth engine to own and improve Net Revenue Retention (NRR). Drive customer adoption of AI capabilities and automate internal operations to scale efficiency and reduce churn.