Technical Support Engineer

Role overview Resolve advanced technical issues for customers using a software platform that supports winery direct-to-consumer operations. Take ownership of escalated cases involving payments, hardware, connectivity, APIs, or integrations, and guide each issue through resolution or a clear escalation. Work with support, engineering, product, and payments colleagues to identify causes, keep customers informed, and improve support resources.

Responsibilities - Manage cases across Level 1 and Level 2 queues, meeting response and service standards while providing clear updates. - Reproduce and troubleshoot complex issues involving payment terminals, connectivity, REST APIs, webhooks, third-party integrations, and website implementations. - Develop and confirm workarounds or solutions; escalate high-impact cases through the appropriate channels. - Document suspected product defects with reproduction steps, evidence, customer impact, and available workarounds. - Coordinate with product, development, payments, and support teams to resolve issues and communicate progress. - Explain platform features to customers, improve knowledge resources, and support Level 1 teammates as a technical resource.

Requirements - 2+ years in Level 2 or advanced technical support, preferably in a software-as-a-service or technology environment. - Hands-on experience troubleshooting REST APIs, such as with Postman, along with webhooks and external integrations. - Experience diagnosing payment systems, hardware terminals, and connectivity problems. - Working knowledge of HTML, CSS, and JavaScript for diagnosing implementation issues. - Experience using a ticket or case management system; strong written and verbal communication, customer de-escalation, and troubleshooting skills. - Must be located in Canada’s Eastern Time zone.

Nice to have - Experience with HubSpot.

Benefits and work setup - Benefits include medical, extended health and long-term disability coverage, dental and vision plans, an employer-matched retirement savings plan, a health spending account, and flexible paid time off.