Senior Director, Customer Retention & Growth (Americas)
Full-time
Sysaid Technologies
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)
Experience
- 10+ years in SaaS Customer Success, Account Management, or Growth
- 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
Vacancy posted 10 hours ago
Similar jobs that could be interesting for youBased on the Senior Director, Customer Retention & Growth (Americas) in Toronto, ON vacancy
- ...office, 1 day remote) Territory: North America Reports to: Chief Revenue Officer... ...SysAid is looking for a VP of Sales, Customer Success & Growth to lead our North America go-to-market... ...leadership role—you will own new business, retention, and expansion, and you will be...SeniorFull timeSummer holidayWork at officeRemote work
$110k - $125k per year
...from JENNY BIRD , and I am the Sr. Director of Retention Marketing and Client Experience. I joined... ...leading our strategy for retaining new customers and crafting amazing experiences to celebrate... ...Opportunity: We are looking for a Senior Retention Manager to join our Marketing...SeniorFull timeSummer workWork at officeFlexible hours- ...event platform designed to drive revenue growth and foster meaningful connections at in-person... ...; can vary according to portfolio): Retention Rate NPS and CSAT score... ...outcomes that create meaningful value for our customers, team members, and partners. Human :...SuggestedLong term contractFull timeRemote workWork from home
$190k - $240k per year
...next Vice President, Client Growth . Salary: $190,000 - $240,000... ...and value to our clients, customers, and communities. Our purpose... ...transforming account management from a retention-focused function into a driver... ..., including influencing senior stakeholders and working with...SeniorLong term contractFull timeContract workFor contractorsLocal areaFlexible hours$160k - $189k per year
...The Director, Customer Success is a senior leadership role responsible for driving retention, expansion, and long‑term customer value across a strategic Enterprise portfolio of B2B SaaS customers. This role owns excellence in execution—translating strategy into outcomes...SeniorLong term contractPermanent employmentFull timeWork at officeFlexible hours- ...MISSION The Smart Factory Customer Success Manager is the primary... ...plans before they become retention risks Lead renewal conversations... ...across plant managers, CI directors, operations leaders, and executive... ...Triage technical and growth issues, coordinating across Product...Full timeContract workInternshipRemote workFlexible hours
$70k - $80k per year
...from JENNY BIRD , and I am the Sr. Director of Retention Marketing and Client Experience. I joined... ...leading our strategy for retaining new customers and crafting amazing experiences to celebrate... ...a strong work ethic, and support the growth of their peers through establishing...SeniorFull timeSummer workInternshipWork at officeFlexible hours- ...platforms. The Team Our Customer Success organization is... ...customer value, driving Net Revenue Retention, and helping customers achieve... ...’re investing in a dedicated Growth Customer Success team focused... ...strategy. Reporting to the Director of Customer Success, you’ll own...Full timeInternshipRemote work
- ...know you! The Work Reporting to the Senior Director, Strategy and Operations, and working... ...management, the Senior Manager, Mortgage Retention and HELOC Strategy is responsible for devising... ...launching initiatives to drive maximum customer retention and delightful customer...SeniorHourly payPermanent employmentFull timeInternshipWork at office
- ...take JOLT to market and how Marketing contributes directly to that growth. Based in Toronto, you’ll primarily support our growing U.S.... ...markets. You’ll work closely with Marketing, Media Sales and senior commercial leaders to grow JOLT’s presence with advertisers, agencies...SeniorFull time
$76k - $93.5k per year
...clients and Account Managers and is responsible for customer service, collaborating with clients and the... ...measurements are up to date and actioned. The Director of Customer Relations is responsible for client retention and growth with existing and new clients and ensuring operational...SeniorContract workWork at officeShift work- ...ROLE SMYTHE is seeking a CRM & Retention Manager to own retention engine, from... ...strategy, digital loyalty mechanics, and customer lifetime value growth. Sitting at the centre of the... .... You will report directly to the Director of Marketing and lead the Customer Marketing...Long term contractFull timeContract work
$144k - $154k per year
Director of UX, Growth Location: Toronto or New York Team: UX, Growth Mega-Alliance Level: Director... ...right person there's a clear path to Senior Director as the alliance scales. Reports... ...company, reaching more than 6 million customers across 16 markets through a portfolio of...SeniorFull time- ...A career as a Senior Director within Fund Accounting , under Investment Operations , at National Bank means acting as an operational and... ...communication, and enable rapid ownership of operational issues and growth-related priorities Collaborate with internal and external...SeniorFull timeLocal areaFlexible hours
- ...infrastructure investments will occur across North America. Infrastructure includes the... ...Looking For? Citylitics is seeking a Director of Customer Enablement to own the customer journey... ...leader central to our revenue growth, this role requires an in-office presence...Full timeInternshipWork at office
- ...Facebook to stay locked in. Position Overview The Director, Growth & Revenue Marketing at Activate works under the direction of... ..., lifecycle marketing, CRM, demand generation, and customer retention across Activate corporate stores, ensuring all marketing activity...Permanent employmentFull timeCasual workInternshipWork at officeLocal areaRemote work
- ...We are looking for a data-obsessed, technically-fluent Retention Specialist to lead our customer lifecycle strategy. You aren’t just "sending emails", you... ..., and Push notification strategies while pioneering new growth frontiers like WhatsApp. The ideal candidate lives...Full timeWorldwide
$141k - $170k per year
...just be in the right place! We’re looking for a Senior Manager, Customer Implementation to lead Lightspeed’s North America Retail onboarding team, responsible for... ...time-to-value, product adoption, and early-stage retention. This role owns onboarding strategy, execution,...SeniorFull timeInternshipWork at officeRemote workFlexible hours3 days per week$97k per year
...intimate apparel brands in North America and are globally recognized as... .... We reach over 3 million customers through our online stores, Knix... ...are the go-to for all things retention for Kt by Knix. While a large... ...channels, but will partner with growth, affiliates, and brand for execution...Hourly payPermanent employmentFull timeShift work- ...expand our presence in North America, we are seeking an experienced... ...professional to drive business growth and strengthen relationships with... ...opportunities, engaging with senior decision-makers, and helping... ...Solactive's index capabilities and custom index solutions as strategic...SeniorLong term contractFull time
$100k per year
...solving hard problems. We are growing our team and looking for contributors of all seniorities. At Tenstorrent, we are building open, scalable compute for real AI workloads. As Director of Customer Engineering, you own the technical relationship with strategic customers and...Permanent employmentFull time- ...making a real difference for our customers. Impact: A strong... ...grow, innovate, and succeed. Growth: Connect commercial growth to... ...primary growth market, North America presents significant opportunities... ...~ Engage confidently with Director, VP, and executive-level stakeholders...SeniorLong term contractFull time
- ...Colgate-Palmolive, a caring, innovative growth company reimagining a healthier future... ...Job Summary The Hill’s Canada Customer Development Director is responsible for leading the Customer... ...equivalent combination of education and senior commercial experience) Pet industry...SeniorLong term contractWork at officeLocal areaRelocation package
$115k - $130k per year
...strong culture of transparency, growth, and human connection. Whether... ...Role As Controller, North America, you will play a key role in... ...developed. Reporting to the Director, Finance, you'll partner closely... ..., including 2+ years in a senior or supervisory role. ~ CPA designation...SeniorFull timeContract workInterim roleWork at officeWorldwideFlexible hours$80k - $100k per year
...-growing FinTech companies in North America, Mortgage Automator is customer-centric, ambitious, and deeply rooted... ...The Role We’re looking for a Senior Customer Success Manager to serve as... ...capabilities, driving long-term health, retention, and expansion. Key...SeniorLong term contractFull timeWork at officeWork from homeFlexible hours- ...to data scientists. Our Commercial Growth Sales Team helps our customers be more productive while still providing... ...About the Role As the Regional Director, you will drive revenue and ensure... ...enhances conversion and maximizes customer value at every stage. By gathering product...Long term contractFull timeInternshipWorldwide
$145k - $170k per year
...trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart. Position Summary: We're looking for a Director, Growth Marketing to own and optimize League's demand generation engine. This is a pipeline role, not a brand awareness role. You'll set...Full timeFor contractorsWork at officeRemote workFlexible hours$155k - $175k per year
...Leeds and Dublin. We’re looking for a Senior Manager, Cohort Growth – Casino to execute the strategy for growing... ...maximizing player volume and value across the customer lifecycle. You’ll partner closely with the Senior Director of Growth to bridge the gap between...SeniorLong term contractFull timeSeasonal work$162k - $198k per year
...outcomes, not outputs. We start with real customer problems and build solutions that... ...we exist to get them off of. As Senior Product Manager, Growth (Activation), you own that crossing.... ...activation metric that actually predicts retention and revenue, instrument it, monitor...SeniorLong term contractFull timeInternship1 day per week$155k - $165k per year
...hands-on builder? We are looking for a Senior Growth Marketing Manager to serve as a "player-... ...everything from top-of-funnel acquisition to customer upsell and advocacy. If you are a... ...and acquisition to customer activation, retention, and expansion. Design and execute persona...SeniorFull timeInternshipFlexible hours
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Senior Director, Customer Retention & Growth (Americas). Be the first to apply!
Related searches
- remote customer service manager Toronto, ON
- customer service supervisor housing construction Toronto, ON
- customer service manager Toronto, ON
- senior customer service manager Toronto, ON
- customer service manager - retail Toronto, ON
- senior manager risk management Toronto, ON
- pega senior system architect Toronto, ON
- senior electrical engineer Toronto, ON
- senior executive Toronto, ON
- senior network engineer Toronto, ON