Customer Success Training Program Jobs in Ontario

The Role 

The Director of Customer Success leads the post-sale customer lifecycle across all customer segments, ensuring customers realize measurable value, adopt solutions effectively, and renew and expand over time. This role is accountable for building and scaling a high-performing Customer Success organization operating under a "One Account, One Owner" model, with clear ownership of customer outcomes across Strategic, Enterprise, State, and Transactional accounts.  

The Director defines how Customer Success operates-establishing engagement models, operating cadence, and cross-functional alignment-while ensuring consistent execution across the core pillars of Strategic Engagement, Adoption, Expansion, and Retention. The role partners closely with Sales, Project Delivery/Onboarding, Support, Product, and Marketing to deliver a seamless and scalable customer experience. 

This job posting is being used to fill an existing vacancy.

 What You Do 

Customer Success Strategy & Execution 

• Execute Customer Success strategies across all customer segments, ensuring alignment to company growth and retention objectives. 
• Establish standardized customer lifecycle motions, including success planning, business reviews, adoption programs, and renewal readiness. 
• Ensure a proactive, outcome-driven approach to customer engagement focused on value realization and measurable impact. 
• Build scalable processes and playbooks that reduce duplication and ensure consistency across Customer Success teams. 

Operating Model & Segmentation 

• Lead a multi-tier engagement model across Strategic, State, Enterprise, and Transactional accounts. 
• Operationalize a hub-and-spoke model, where Customer Success Managers own relationships and provide general project knowledge and engage specialists for additional targeted support.  
• Ensure role clarity across Customer Success and adjacent teams, reinforcing boundaries around support, project delivery/onboarding, and sales ownership. 
• Continuously refine segmentation and coverage models to balance engagement with scalable programs. 
• Own end-to-end retention and renewals strategy, by executing a proactive renewal motion (initiating 180-90 days pre-expiry), enforcing disciplined commercial rigor across procurement cycles, and operationalizing cross-functional support to drive on-time renewals, maximize ARR retention and price increases, mitigate churn risk, and ensure consistent value realization for customers. 

Cross-Functional Leadership 

• Partner with Sales, Project Delivery/Onboarding, Support, Product, and Marketing to deliver a cohesive customer experience. 
• Establish clear handoffs and accountability across onboarding, Customer Success, and renewals. 
• Serve as an escalation point for high-risk or high-impact customer situations to ensure satisfactory customer resolution and support. 
• Provide Voice of Customer insights to influence product roadmap and go-to-market strategy. 

Data, Reporting & Performance Management 

• Own and drive gross and net revenue retention across the customer portfolio, aligning performance to company financial targets.  
• Define and operationalize success metrics across Customer Success and Renewals, including retention, on-time renewals, customer health, business review quality, and expansion pipeline influence.  
• Design and execute structured renewal motions, incorporating early engagement, procurement tracking, and risk mitigation to ensure predictable, on-time renewals.  
• Leading the Renewals team and partnering with sales teams to drive expansion opportunities and maximize lifetime value.  
• Proactively identify churn risks through health, adoption, and engagement signals; implement targeted save plans to mitigate attrition.  
• Establish and maintain customer health scoring models to guide segmentation, prioritization, and intervention strategies.  
• Drive a consistent operating cadence (e.g., pipeline reviews, business reviews) to assess customer health, renewal forecasts, and team performance; coach proactively and enforce accountability.  
• Ensure CRM hygiene and data integrity (e.g., Salesforce), enabling accurate forecasting, renewal visibility, and revenue reporting.  
• Analyze systemic risks and performance trends, translating insights into process improvements, playbook enhancements, and program investments.  
• Oversee automated customer engagement programs (e.g., campaigns, webinars, lifecycle education, newsletters) to scale impact and drive adoption.  
• Communicate performance, risks, and strategic recommendations clearly to GTM and Executive Leadership, ensuring alignment and informed decision-making. 

 What You Bring 

• Bachelor's degree in Business Administration, Communications, or a related field. 
• 10+ years of experience in Customer Success, Account Management, or related SaaS roles. 
• 5+ years of experience leading teams and developing people leaders. 
• Proven experience owning retention, renewals, and customer growth metrics at scale. 
• Strong understanding of Customer Success operating models, including segmentation and scaled engagement strategies. 
• Experience building and standardizing processes, playbooks, and performance frameworks. 
• Strong data orientation, with the ability to translate insights into action and measurable outcomes. 
• Exceptional collaboration and leadership skills, with the ability to align cross-functional teams. 
• Excellent communication and executive presence, with experience engaging senior stakeholders. 
• Ability to operate effectively in complex, high-accountability environments. 
• Experience in public sector, GovTech, or public safety SaaS environments preferred. 

Note: This position requires a security clearance from the Government of Canada. Candidates must be legally authorized to work in Canada and must successfully obtain and maintain a Reliability security clearance. Please note that specific customer contracts may impose additional security verification requirements. Obtaining and maintaining all required security clearances is a condition of employment. For more information on the Government of Canada's security screening process, please visit Public Services and Procurement Canada.
Versaterm is committed to fair and equitable compensation that is competitive, consistent, and aligned with the value each role contributes to our organization. The starting salary for this position will be dependent upon many factors, such as the successful candidate's skills, experience, education, training as well as internal equity, market data, and business needs. In addition to base salary and our comprehensive benefits offering, some roles may also be eligible for variable compensation such as incentive plans or discretionary performance bonuses.