Job Description: 

The Opportunity

This is not a traditional executive leadership role. We're looking for a player-coach; someone who has built their career from the ground up within technical support organizations.

You understand what it's like to troubleshoot hardware in the field, diagnose software issues, manage customer escalations, and support enterprise clients. While you're now an experienced leader, you're still comfortable rolling up your sleeves when needed.

You'll inherit two experienced leaders and a team of more than 20 technical professionals while partnering closely with the CEO to shape the future of our support organization.

You'll have the autonomy to improve processes, introduce new technologies, implement AI-driven efficiencies, strengthen documentation, establish operational rigor, and build scalable support practices that support our continued growth.

What You'll Be Responsible For

Executive Customer Support Leadership

Champion a customer-first support organization built around accountability, responsiveness, transparency, and operational excellence. Serve as the executive escalation point for our largest enterprise customers, stepping into critical customer 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.

Operational Leadership

Evaluate every aspect of the current support organization and continuously improve:

• Processes

• Documentation

• Team structure

• Escalation procedures

• Knowledge management

• Automation

• Customer communications

• Service quality

You'll be empowered to redesign workflows and implement best practices that improve both customer experience and internal efficiency.

Technical Leadership

Maintain enough technical depth to effectively support your teams during complex customer issues. While this role is not expected to write code or perform day-to-day support work, you should comfortably understand:

• Enterprise software

• Hardware troubleshooting

• Point-of-sale environments

• Enterprise networking fundamentals

• Operating systems

• Cloud platforms

• Customer deployments

• Software integrations

Many customer issues involve both software and physical hardware, requiring leaders who understand how the two interact within real-world environments.

AI & Continuous Improvement

One of the key initiatives for this role will be introducing AI and automation into the support organization.

You'll identify opportunities to improve efficiency through:

• AI-assisted support

• Knowledge management

• Documentation automation

• Ticket routing

• Trend identification

• Root cause analysis

• Customer self-service

• Operational reporting

Metrics & Operational Excellence

Develop meaningful KPIs and SLAs that provide visibility into support performance for both internal leadership and enterprise customers.

Enterprise customers frequently request operational reporting, making strong analytical and reporting capabilities essential.

Budget & Strategic Planning

Own departmental budgeting, forecasting, resource planning, vendor management, and technology investments.Develop annual operational plans that balance customer experience, team growth, operational efficiency, and business objectives.

What Success Looks Like

The successful candidate will:

• Build trust quickly with both customers and employees.

• Bring structure and accountability to support operations.

• Improve documentation and operational consistency.

• Introduce AI and automation where appropriate.

• Strengthen leadership across multiple technical teams.

• Improve KPI reporting and executive visibility.

• Reduce recurring customer issues through proactive analysis.

• Create scalable processes that support future company growth.

Who You Are

You're someone who enjoys solving difficult operational problems. You've likely grown your career through Technical Support, IT Operations, Infrastructure, Customer Success Engineering, or Enterprise Support before moving into leadership.

You still enjoy understanding technical problems, asking thoughtful questions, mentoring managers, and occasionally jumping into customer situations when your experience can help move things forward. You're equally comfortable presenting operational metrics to a CEO as you are coaching a frontline manager or speaking directly with an enterprise customer during a critical escalation.

Most importantly, you lead by example.

Qualifications

Required

• 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.

• ITIL Foundation certification (or higher).

Preferred

• Experience supporting enterprise Point-of-Sale (POS) platforms.

• Experience working with both hardware and software products.

• Experience leading organizations through significant growth (approximately $5M to $40M+ ARR or equivalent operational scale).

• Experience implementing AI or automation within technical support organizations.

• Experience with AWS cloud environments (GCP exposure is beneficial but not required).

• Experience supporting enterprise customers across healthcare, hospitality, retail, or foodservice industries.

Working Model

• Hybrid (Toronto office) - 3 days in office 

• New leaders should expect to spend approximately five days per week in the office during onboarding to develop a deep understanding of the product, people, and business before transitioning to a three-day hybrid schedule.

• Quarterly travel throughout North America to support strategic customer relationships and key business initiatives.

Business Unit: 

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More About Jonas Software:

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, to name a few. Within these markets, 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.