[Hiring] Senior Technical Support Specialist @PocketHealth

Role Description

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.

• Diagnose and resolve integration issues across diverse Windows environments.
• Leverage 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.

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.

Qualifications

• 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.
• 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.

Requirements

• 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.
• 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.

Benefits

• Working remotely.
• 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.