Senior Technical Support Specialist

PocketHealth•Toronto, ON

1d•CA$72,000 - CA$80,000•Remote

About The Position

PocketHealth is looking for a Senior Technical Support Specialist to support our healthcare implementations across provider environments. In this role, you will ensure the systems that providers and patients rely on run seamlessly, taking a hands-on approach to complex PACS and network troubleshooting. You will diagnose and resolve integration issues across diverse Windows environments, leveraging network diagnostics (firewall rules, telnet, connectivity) and PACS-related workflows (C-ECHO, query/retrieve, and imaging import). This role is designed to transition into our Technical Implementation team over time, where you will partner directly with project teams and external stakeholders as the technical authority on deployment projects. This team protects the reliability of healthcare workflows. The issues you resolve directly impact a provider's ability to access critical medical imaging and a patient's ability to access their records.

Requirements

3+ years supporting production software systems.
Experience with SQLite / DB Browser (Comfortable writing queries to investigate data).
Experience with Retool or similar no-code admin tools.
Experience with Salesforce Service Cloud or similar ticketing systems.
Experience with Datadog or similar application log analysis tools.
Experience with 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.
Strong communication skills with the ability to confidently lead technical calls with both internal teams and external non-technical stakeholders.
Highly organized and results-focused.

Nice To Haves

Background in IT service desks or technical support operating within an ITIL framework.
Hands-on PACS / RIS / EMR system experience and knowledge of DICOM, HL7, or FHIR standards.
Experience working in healthcare or HealthTech environments with familiarity in HIPAA, PHIPA, or SOC2 compliance.
Prior experience leading large-scale, end-to-end technical implementations or deployments with external clients.
A genuine passion for improving the provider and patient experience in healthcare.

Responsibilities

Investigate and resolve escalated technical incidents impacting providers and patients, consistently meeting or exceeding SLAs for high-impact cases.
Diagnose issues at the system level, including configuration, integrations, and workflow behavior.
Query databases directly to validate application data, analyze behavior, and isolate root causes.
Identify, replicate, and document software bugs clearly before escalating them to internal engineering teams.
Manage Windows Server environments, analyzing how CPU, memory, and disk allocation contribute to performance degradation or system issues.
Administer and troubleshoot SQLite databases, running direct queries to validate system health.
Troubleshoot authentication issues, including AD/LDAP-related failures, with a strong understanding of how Active Directory manages user and group authentication steps.
Document repeatable troubleshooting processes, system behaviors, and workarounds in Notion and Salesforce Service Cloud.
Serve as the internal technical expert and go-to resource for complex infrastructure questions, contributing continuously to process and tooling improvements.