Vice President, Customer Success - Acute and Payer

Location: USA - Remote | Canada - Remote | Mississauga - Hybrid

Travel to Office expectations: For Remote Roles, in-office events will require travel to and from the Mississauga and/or Salt Lake City office, including onboarding, team events, semi-annual and annual team meetings. For Hybrid Roles, weekly/bi-weekly/monthly in-office events with your specific team are required, and you must reside within commutable distance to the specified office.

About the role

Reporting to the SVP, Customer Success & Support, the Vice President, Customer Success will lead PointClickCare’s post-sale customer relationships across the Acute and Payer segments. This role is accountable for driving customer retention, growth, and long-term value realization across a portfolio representing approximately $112M in ARR. The successful candidate will establish and execute customer success strategies that improve Net Revenue Retention (NRR), Gross Revenue Retention (GRR), and expansion revenue while fostering strong executive-level customer relationships. As a key member of the leadership team, this individual will build and lead a high-performing Customer Success organization, partner cross-functionally across Sales, Product, Professional Services, and Support, and ensure customers achieve measurable outcomes through PointClickCare’s solutions.

Responsibilities

• Lead and execute a comprehensive retention and growth strategy for Acute and Payer customers, with accountability for NRR, GRR, expansion revenue, customer health, and overall portfolio performance.
• Define and operationalize customer success frameworks, including health score models, executive business reviews, success planning, risk identification processes, and proactive retention motions.
• Manage and grow a customer portfolio representing approximately $112M in ARR through strong customer engagement, value realization, and strategic relationship management.
• Lead Customer Engagement Transformation initiatives, including customer success program enhancements, value delivery frameworks, and scalable operating models that support customer outcomes and organizational growth.
• Drive Customer Success alignment with go-to-market strategies in partnership with Sales and Revenue leadership to support renewals, customer advocacy, and expansion opportunities.
• Establish and lead cross-functional customer risk reviews, ensuring customer-impacting issues are identified, escalated, and resolved efficiently while driving accountability across teams.
• Champion strategic AI adoption by embedding AI into team strategy, operating models, productivity initiatives, and decision-making practices while promoting responsible and effective use of AI technologies.
• Build, develop, and inspire a high-performing Customer Success organization of approximately 25 team members, including leaders and individual contributors across Enterprise and Mid-Market customer segments.
• Recruit, mentor, and retain top talent by establishing clear performance expectations, coaching frameworks, career development pathways, and a culture focused on accountability, collaboration, and customer outcomes.
• Design and evolve organizational structures, account coverage models, and customer engagement approaches to support the scale and complexity of Acute and Payer customers.
• Build trusted relationships with executive stakeholders across health systems, hospitals, payer organizations, and convenors, serving as a strategic advisor and escalation point for critical customer matters.
• Partner closely with Product Management to provide structured customer feedback, influence roadmap priorities, and advocate for enhancements that drive measurable customer value.
• Collaborate with Professional Services, Implementation, Support, Finance, Legal, and Sales teams to deliver seamless customer experiences and optimize long-term customer and company value.
• Represent PointClickCare at industry events, customer forums, and executive engagements, contributing thought leadership and strengthening the company’s presence within the healthcare ecosystem.

Requirements

• Bachelor’s degree required; MBA or advanced degree in a healthcare-related field is considered an asset.
• 10+ years of Customer Success, Account Management, or related leadership experience, including at least 5 years leading Customer Success teams in a complex B2B SaaS environment.
• 10+ years of U.S. healthcare payer, provider, and convenor experience (preferred).
• Demonstrated success driving retention, expansion, NRR, and GRR outcomes across large, multi-stakeholder customer portfolios.
• Proven experience building, scaling, and transforming Customer Success organizations through periods of growth, change, and operational maturity.
• Strong executive presence with the ability to influence and build relationships with C-suite stakeholders, both internally and externally.
• Exceptional commercial acumen with experience partnering closely with Sales teams on renewals, customer growth strategies, and revenue outcomes.
• Demonstrated ability to collaborate cross-functionally and influence outcomes across Product, Sales, Implementation, Professional Services, and Support organizations.
• Experience leveraging customer success and CRM platforms such as Gainsight and Salesforce to drive data-informed decision-making and operational excellence.
• Deep understanding of the acute care and/or payer healthcare landscape, including market dynamics, regulatory considerations, reimbursement models, and customer operational challenges.
• Comfortable learning new technologies, adapting to evolving priorities, and leading teams in a fast-paced environment.

Benefits

• Benefits starting from Day 1
• Retirement Plan Matching (RRSP & 401K)
• Flexible Paid Time Off
• Lifestyle/Wellness Spending Account
• Parental & Caregiver Leaves
• Fertility & Adoption Support
• Continuous Development Support Program
• Employee Assistance Program
• Learning Programs & Resources
• Employee Recognition

Pay

This role offers a competitive base salary + bonus + benefits, non-overtime eligible. Salary ranges are determined by job and level, with individual compensation based on job-related skills, relevant experience, and work location.