Senior Technical Support Specialist

PocketHealth

Senior Technical Support Specialist enabling hospitals to empower patients with a better healthcare experience. Troubleshooting complex issues and managing integrations across Windows environments.

Posted 6/12/2026full-timeRemote • 🇨🇦 CanadaSenior💰 CA$72,000 - CA$80,000 per yearWebsite

Tech Stack

Tools & technologies

CloudFirewallsSQLiteTCP/IP

About the role

Key responsibilities & impact

Resolve Critical Issues: Investigate and resolve escalated technical incidents impacting providers and patients, consistently meeting or exceeding SLAs for high-impact cases.
Deep-Dive Troubleshooting: Diagnose issues at the system level, including configuration, integrations, and workflow behavior. We look for candidates who understand why a system is failing, not just those who restart services.
Data Validation: Query databases directly to validate application data, analyze behavior, and isolate root causes.
Bug Management: Identify, replicate, and document software bugs clearly before escalating them to internal engineering teams.
Windows Server Management: Manage Windows Server environments, analyzing how CPU, memory, and disk allocation contribute to performance degradation or system issues.
Database Administration: Administer and troubleshoot SQLite databases, running direct queries to validate system health.
Identity & Access Management: Troubleshoot authentication issues, including AD/LDAP-related failures, with a strong understanding of how Active Directory manages user and group authentication steps.
Knowledge Sharing: Document repeatable troubleshooting processes, system behaviors, and workarounds in Notion and Salesforce Service Cloud.
Cross-Functional Collaboration: Serve as the internal technical expert and go-to resource for complex infrastructure questions, contributing continuously to process and tooling improvements.

Requirements

What you’ll need

3+ years supporting production software systems
Experience with our Tech Stack (or equivalent):
- Databases: SQLite / DB Browser (Comfortable writing queries to investigate data).
- Internal Tooling: Retool or similar no-code admin tools.
- Ticketing: Salesforce Service Cloud or similar.
- Observability: Datadog or similar application log analysis tools.
- Analytics & Docs: Sigma (BI/Dashboarding) and Notion (Knowledge Base).
Experience troubleshooting complex applications at the system level, including configurations, integrations, and complex workflows.
Hands-on experience managing both Windows Desktop and Server environments, including resource management (CPU, memory, disk) and Active Directory/Group Policy.
Confident troubleshooting network connectivity issues using firewalls, TCP/IP, telnet, and basic LAN diagnostics.

Benefits

Comp & perks

Competitive salaries and benefits (including stock options for every employee!)
Four weeks of paid time off
Unlimited paid wellness days
Extended mental health coverage
16 weeks of parental leave top-up

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

troubleshootingdata validationbug managementWindows Server managementdatabase administrationidentity and access managementnetwork connectivity troubleshootingsystem configurationapplication integrationworkflow analysis

Soft Skills

cross-functional collaborationknowledge sharingproblem-solvingcommunicationtechnical expertise