Technical Support Engineer (Healthcare)

TL;DR

Technical Support Engineer (Healthcare): Acting as the primary escalation layer for technical issues across the platform with an accent on investigation, reproduction, and root cause analysis. Focus on solving complex product and data-layer problems using SQL and observability tools to protect platform reliability.

Location: Remote (Non-U.S.)

Company

A remote-first Y-Combinator company operating a marketplace that connects healthcare professionals with workplaces across the U.S.

What you will do

• Monitor escalation channels and the Technical Support queue in Zendesk to identify systemic problems.
• Investigate complex product and data-layer issues using SQL, Datadog, and internal dashboards.
• Manage live incidents end-to-end, coordinating between Support, Engineering, and Product teams.
• Implement and test technical fixes before handing them off to Engineering for final review.
• Perform Root Cause Analysis (RCA) and develop troubleshooting guides to reduce issue recurrence.
• Maintain operational workflows and suggest structured improvements based on recurring patterns.

Requirements

• Proficiency with observability tools (e.g., Datadog) and SQL for data interrogation.
• Ability to reason about APIs, backend configurations, and distinguish between UI, data, and code-level problems.
• High level of ownership, managing problems from first report to confirmed resolution.
• Ability to remain structured and calm during high-pressure live incidents.
• Professional-level English communication (written and verbal).
• Availability to work 5 days within a 7-day schedule, including weekends.

Nice to have

• Experience with Sentry, Snowflake, or similar analytics and observability tooling.
• Background in SRE, incident response, or an engineering-adjacent function.
• Exposure to AI-assisted coding or agent tooling.
• Previous experience in large-scale Ops, Support, or CX environments.

Culture & Benefits

• Remote-first work environment with a global team.
• High-ownership culture with "uncomfortably high standards."
• Opportunity to work at a profitable, fast-growing Y-Combinator company.
• Impact-driven role protecting reliability for hundreds of thousands of healthcare workers.

Hiring process

• Application review.
• Skills assessment via Case Study.
• Case interview with the Technical Support Team Lead.
• Final interview with the Head of Worker Experience.