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 A I to

- :Help customers achieve faster, measurable outcome
- sDrive proactive, data-driven engagemen
- tScale internal operations without linear headcount growt

**h

Key Responsibilitie**

s:1. Own Net Revenue Retention (NR

- R)Drive strategy acros
- s:Churn reducti
- onExpansion (upsell, cross-sel
- l)Build AI-enhanced forecasting models fo
- r:Churn ri
- skExpansion propensi
- tyEstablish clear ownership across CSMs, AMs, and lifecycle stag

es2. Drive AI-Powered Adoption & Time-to-Val

- ueEnsure customers adop
- t:Core ITSM capabiliti
- esSpaces (new interfac
- e)SysAid’ s agentic AI capabiliti
- esPartner with Product & PS t
- o:Embed AI into onboarding journeys (e.g., AI-generated onboarding plan
- s)Delive r guided, automated adoption experienc
- esOperationaliz e AI-driven health scoring and next-best actio

ns3. Build a Scalable, AI-Driven Growth Engi

- neDesign a structured expansion motion powered by A
- I:Identify expansion signals automatically (usage, gaps, trigger
- s)Use AI to generat
- e:Deal insigh
- tsBusiness cas
- esPricing recommendatio
- nsEquip teams wit h AI copilo ts fo
- r:Account planni
- ngQBR preparati
- onExecutive storytelli
- ngShift from reactive selling t o predictive, insight-led grow

th4. Reduce Churn Through Proactive, Automated Risk Manageme

- ntBuil d AI agen ts t
- o:Continuously monitor customer heal
- thDetect risk patterns (product usage, support friction, sentimen




- t)Trigger automated or human-led interventio
- nsMove from: Reactive service tickets → t o Predictive, system-driven retention pla
- ysIdentify systemic churn drivers (e.g., Spaces gaps, onboarding issues) and close the loop with Produ

ct5. Lead Agentic AI Transformation (Internal + Customer-Facin g)Customer-Facing

- AIDefine how customers should use SysAid’s agentic AI t
- o:Automate IT workflo
- wsImprove service delive
- ryIncrease ROI from the platfo
- rmPartner with Product t
- o:Package AI use cases into transparent value propositio
- nsDefin e “when to use an agent” vs traditional workflows/integratio
- nsEnsure CSMs can articulate and drive adoption of AI outcomes—not just featur

esInternal AI & Automati

- onDeploy AI agents to transform post-sales operation
- s:Automated QBR generati
- onCall summaries and action tracki
- ngTicket clustering and root cause analys
- isRenewal and expansion insigh
- tsIncreas e coverage per C SM through automation and AI augmentati
- onRedesign workflows to minimize manual work and maximize customer-facing ti

me6. Elevate Customer Experience Through Intelligent Feedback Loo

- psUse AI t
- o:Aggregate and cluster customer feedback (support tickets, calls, survey
- s)Identify product and experience trends at sca
- leReduce noise from service records and surfac e true systemic issu
- esCreate structured, data-backed feedback loops into Product (especially for Space

s)7. Redefine Roles for an AI-First Organizati

- onEvolve team responsibilitie
- s:CSMs → Outcome Orchestrato
- rsAMs → Growth Strategis
- tsSupport → AI Superviso
- rsTrain teams t
- o:Leverage AI in daily workflo
- wsInterpret AI-generated insigh




- tsFocus on high-value, human interactio

ns8. Build & Lead a High-Performing, AI-Native Te

- amDefine segmentation and coverage models enhanced by
- AIEstablish KPIs acros
- s:Retention & expansi
- onAdoption (including AI feature adoptio
- n)Operational efficiency (automation rates, productivit
- y)Hire and develop talent comfortable operating in a n AI-augmented environme

ntKey Success Metri

- csNet Revenue Retention (NR
- R)Gross Churn Ra
- teExpansion Reven
- ueAdoption o
- f:Core platform (including Space
- s)Agentic AI capabiliti
- esTime-to-Val
- ueCustomer Health Score Accura
- cy% of workflows automated (internal & customer-facin
- g)CSM productivity (accounts per CSM, time spent on strategic vs manual wor

**k)

Experie**

- nce10+ years in SaaS Customer Success, Account Management, or Growth, and at least 5 years in manager ro
- lesProven ownership of retention and expansion targ
- etsExperience leadi ng AI/automation initiati ves in customer-facing teams (strong pl
- us)Background in ITSM, enterprise SaaS, or workflow platforms prefer

**red

Capabili**

- tiesStrong understanding
- of:SaaS retention mechanics (NRR driv
- ers)Customer lifecycle de
- signAI/automation use cases in post-s
- alesAbility to translate AI capabilities i nto customer business v
- alueData-driven and systems thi

**nker

Leadership T**

- raitsCommercially oriented (growth min
- dset)Comfortable leading thr ough product and platform transi
- tionsBalances strategic thinking with operational exec
- utionStrong cross-functional influencer (Product, Sales, Enginee

**ring)

Why This Role M**

attersSysAid is at a pivotal m
- oment:Transitioning platform (S
- paces)Expanding AI capabi
- litiesSignificant untapped growth in the installe

d baseThis role will define how S
- ysAid:Scales Customer Success with AI (without linear cost g
- rowth)Differentiates th rough intelligent, automated customer exper
- iencesTurns AI i nto a core driver of retention and exp

ansion

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