Vice President, Support & Technical Operations

Jonas Software•Toronto, ON

2d•Hybrid

About The Position

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.

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.
ITIL Foundation certification (or higher).

Nice To Haves

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.

Responsibilities

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.
Evaluate every aspect of the current support organization and continuously improve: Processes, Documentation, Team structure, Escalation procedures, Knowledge management, Automation, Customer communications, Service quality.
Redesign workflows and implement best practices that improve both customer experience and internal efficiency.
Maintain enough technical depth to effectively support your teams during complex customer issues.
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 that provide visibility into support performance for both internal leadership and enterprise customers.
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.