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About the Role

This role is for a player-coach leader in technical support, with experience in troubleshooting, customer escalations, and supporting enterprise clients. You will lead a team of over 20 professionals and partner with the CEO to shape the future of the support organization, with autonomy to improve processes, introduce new technologies, and build scalable support practices.

Responsibilities

• Champion a customer-first support organization built around accountability, responsiveness, transparency, and operational excellence.
• Serve as the executive escalation point for enterprise customers, stepping into critical situations when executive leadership is required.
• Build trusted relationships with enterprise customers while ensuring exceptional communication throughout complex technical incidents.
• Lead structured Severity 1 incident management, executive communications, post-mortems, and root cause analysis.
• Evaluate and continuously improve support organization processes, documentation, team structure, escalation procedures, knowledge management, automation, customer communications, and service quality.
• Redesign workflows and implement best practices to improve customer experience and internal efficiency.
• Maintain technical depth to support teams during complex customer issues, understanding enterprise software, hardware troubleshooting, POS environments, enterprise networking, operating systems, cloud platforms, customer deployments, and software integrations.
• Identify opportunities to improve efficiency through AI-assisted support, knowledge management, documentation automation, ticket routing, trend identification, root cause analysis, customer self-service, and operational reporting.
• Develop meaningful KPIs and SLAs to provide visibility into support performance.
• Own departmental budgeting, forecasting, resource planning, vendor management, and technology investments.
• Develop annual operational plans balancing customer experience, team growth, operational efficiency, and business objectives.

Requirements

• 10+ years of progressive experience in technical support, enterprise software, IT operations, or technical services.
• 5+ years leading managers and multi-disciplinary technical teams.
• Previous hands-on experience in Tier 1 and Tier 2 Technical Support early in your career.
• Experience supporting enterprise software products.
• Strong understanding of both hardware and software support environments.
• Experience leading executive customer escalations.
• Experience establishing KPIs, SLAs, and executive operational reporting.
• Experience managing departmental budgets and annual forecasting.
• Strong documentation, process improvement, and operational excellence experience.
• Experience implementing or improving ITIL-based support processes.

Skills

• Enterprise software
• Hardware troubleshooting
• Point-of-sale environments
• Enterprise networking fundamentals
• Operating systems
• Cloud platforms
• Customer deployments
• Software integrations
• AI-assisted support
• Knowledge management
• Documentation automation
• Ticket routing
• Trend identification
• Root cause analysis
• Customer self-service
• Operational reporting
• KPI development
• SLA establishment
• Budget management
• Forecasting
• Resource planning
• Vendor management
• Technology investment planning
• Process improvement
• Operational excellence
• ITIL-based support processes

Location

• Toronto

Work Type

• Hybrid
• Professional (Fixed Term)

Experience Level

• 10+ years of progressive experience
• 5+ years leading managers

Education Level

• ITIL Foundation certification (or higher)

About the Company

• Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services.
• Jonas is comprised of over 65 distinct brands, each a respected leader in its domain.
• Jonas’ vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of “Software for Life.”
• We are committed to technology, product innovation, quality, and exceptional customer service.
• Jonas Software supports over 60,000 customers in more than 30 countries.
• We employ over 6,000 skilled professionals, including industry experts and technology specialists.
• Across our broader network, we support a global workforce of more than 30,000 employees.
• Headquartered in Canada, Jonas Software has a global footprint with offices around the world.
• We’re a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index.