Job Description

The OpportunityThis is not a traditional executive leadership role. We’re looking for a player‑coach – someone who has built a 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.

Responsibilities

- 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 Severity1 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, and service quality.
- 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.
- Understand enterprise software, hardware troubleshooting, point‑of‑sale environments, enterprise networking fundamentals, operating systems, cloud platforms, customer deployments,



and 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

- Introduce AI and automation into the support organization.
- 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, and metrics.
- Develop meaningful KPIs and SLAs that provide visibility into support performance for both internal leadership and enterprise customers.

- 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.

Success Metrics
- 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

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

- 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 Tier1 and Tier2 Technical Support early in your career.
- Experience supporting enterprise software products and 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 Qualifications
- 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): 3days in office. New leaders should expect to spend approximately five days per week in the office during onboarding before transitioning to a three‑day hybrid schedule. Quarterly travel throughout North America to support strategic customer relationships and key business initiatives.

EEO Statement

Jonas Software is an Equal Prospect Employer.

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📌 Vice President, Support & Technical Operations (Toronto)
🏢 EWS Group
📍 Toronto