Senior Technical Support Specialist

Pockethealth
Pockethealth

IT, Customer Service

Toronto, ON, Canada

Posted on Jun 14, 2026
What if you could personally impact the future of healthcare? As part of the PocketHealth team, you will enable hospitals and clinics across North America — and more importantly, empower over 2 million patients — to discover a better healthcare experience.
PocketHealth is a patient-centric platform that enables hospitals and clinics across North America to share imaging records digitally with patients, instantly and securely. Through our platform, we enable patients to be active and engaged participants in their own care, and take control of their care journey. In addition to image sharing, which is the heart of the PocketHealth platform, we’ve grown our core functionality to enable sharing between hospitals and physicians, as well as instant image retrieval and automated importing capability. PocketHealth is a unified image management solution for over 800 hospitals and clinics across North America. We believe that by placing patients at the center of the record release process, data moves more ethically, easily and securely throughout the care journey, and we’re looking for passionate individuals to help make this vision a reality for millions more patients across North America.

About the Role

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).

Career Growth: 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.

Our Mission: 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.

This job posting is for an existing vacancy. The salary range for this position is $72,000 – $80,000 annually, depending on the experience and expertise you bring to the team. This role is also eligible for equity in the form of stock options and includes a comprehensive health and benefits package.

What you'll be doing:

    Production Support & Escalations

  • 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.

    • Systems & Infrastructure

  • 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.

    • Process & Documentation

  • 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.

What you'll bring:

  • Technical Support: 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).
  • System Diagnostics: Experience troubleshooting complex applications at the system level, including configurations, integrations, and complex workflows.
  • Windows Environments: Hands-on experience managing both Windows Desktop and Server environments, including resource management (CPU, memory, disk) and Active Directory/Group Policy.
  • Networking Fundamentals: Confident troubleshooting network connectivity issues using firewalls, TCP/IP, telnet, and basic LAN diagnostics.
  • Soft Skills: 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 have, but aren't deal breakers:

  • 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.
You can do amazing things at PocketHealth. You can positively impact the healthcare journey for millions of people, while building your career and developing your skills. It doesn’t have to be one or the other. It has been a part of our mission since our founding to empower patients & make healthcare accessible to all, and we know this can only be achieved with a team of diverse perspectives that is representative of the Patient & Provider communities we serve.
People love working here for these reasons and more: working remotely, our competitive salaries and benefits (including stock options for every employee!), four weeks of paid time off, unlimited paid wellness days, extended mental health coverage, and 16 weeks of parental leave top-up.
We’re proud to foster a culture that embraces diversity, equity, and inclusion, and we believe in caring for our employees with the same thoughtfulness we offer our Patients & Providers.
If there are ways we can support you through the recruitment process with an accommodation, please let us know by reaching out to DEI@pocket.health. Applications are accepted via posting only.
See more open positions at Pockethealth