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 toHelp customers achieve faster, measurable outcomesScale internal operations without linear headcount growthKey Responsibilities1. Own Net Revenue Retention (NRR)Churn reductionBuild AI-enhanced forecasting models forExpanpropensitypensiEstablish transparent ownership across CSMs, AMs, and lifecycle stages2. Drive AI-Powered Adoption & Time-to-ValueSpaces (ninterfacefacSysAid's agentic capabilitiesPartner with Product & PSEmbed AI into onboarding journeys (e.G., AI-generated onboarding planDeliver guided, automated adoption experienceses Operationalize AI-driven health scoring and next-best action3. Build a Scalable, AI-Driven Growth EngineDesign a structured expansion motion powered by AIIdentify expansion signals automatically (usage, gaps, triggerUse AI to generateDeal insightsBusinesses casesPricing recommendationsEquip teams with AI copilotsQBR preparationExecutive storytellingShift from reactive selling to predictive, insight-led growth4. Reduce Churn Through Proactive,



Automated Risk ManagementBuild AI agentsContinuously monitor customer healthTrigger automated or human-led interventionMove 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 Produt5. Lead Agentic AI Transformation (Internal + Customer-Facing)Define how customers should use SysAid's agentic AI tto automate workflowsIncrease ROI from the platformPartner with Product toPackage AI use cases into clear value propositionsDefine "when to use an agent" vs traditional workflows/integratioEnsuree CSMs can articulate and drive adoption of AI outcomes, not just featurInternal AI & AutomatiDeploy AI agents to transform post-sales operations:Automated QBR generation, call summaries,s and action trackingTicket clustering and root cause analysisRenewal and expansion insightsIncrease coverage per CSM through automation and AI augmentationRedesign workflows to minimize manual work and maximize customer-facing time6. Elevate Customer Experience Through Intelligent Feedback LoopUse AI toAggregate and cluster customer feedback (support tickets, calls, surveys)yIdentify product and experience trends at scaleReduce noise from service records and surface true system issuesCreate structured, data-backed feedback loops into Product (especially for Space7. Redefine Roles for an AI-First Organization:



Evolve team responsibilitiesTrain teamsLeverage AI in daily workflowsInterpret AI-generated insightsFocus on high-value, human interaction8. Build & Lead a High-Performing, AI-Native TeDefine segmentation and coverage models enhanced byRetention & expansiOperational efficiency (automation rates, productivityHire and develop talent comfortable operating in an AI-augmented environmentKey Success MetricsNet Revenue Retention (NRR)Gross Churn RaExpansion RevenAgentic AI capabilitiesTime-to-ValCustomer Health Score Accuracyof workflows automated (internal & customer-facing)CSM productivity (accounts per CSM, time spent on strategic vs manual work)Experiens10+ years in SaaS Customer Success, Account Management, or Growth, and at least 5 years in manarolesr roProven ownership of retention and expansion targExperience leading AI/automation initiatives in customer-facing teamsBackground in ITSM, enterprise SaaS, or workflow platforms preferredCapabilitsof SaaS retention mechanics (NRR drive)signAI/automation use cases in post-Ability to translate AI capabilities into customer businessData-driven and systems thinkingLeadershipCommercially oriented (growth minmindset). Comfortable leading through product and platform transiBalances strategic thinking with operational execStrong cross-functional influencer (Product, Sales, Engineering)Why This Role MattersExpanding AI capalities Significant untapped growth in the installedThis role will define how SysAid:SysAid: Scales Customer Success with AI (without linear cost gDifferentiates through intelligent, automated customer experTurns AI into a core driver of retention #J-18808-Ljbffr

📌 Director, Customer Retention & Growth (Americas) (Toronto)
🏢 SysAid
📍 Toronto