Technical Support Engineer

ABOUT CLIPBOARD

Our mission is to uplift as many communities as possible. We do this through our app-based marketplace that connects healthcare professionals with the workplaces that need amazing workers. This enables hundreds of thousands of people to achieve financial stability for themselves and their families while providing essential care to millions of people across the U.S.

Founded in 2016, we are a remote-first team of over 1,000 people building a top Y-Combinator company https://www.ycombinator.com/topcompanies/ and have been profitable since 2022. We’re the leader in Long-Term Care staffing and are rapidly expanding into Home Health, Hospitals, and more, meaning we have more work to do than people to do it, and are growing our team to support millions more people and their communities.

OVERVIEW

📍 Remote - Caribbean

Want to sit at the intersection of Support, Engineering, and Product? Clipboard is hiring Technical Support Engineers (TSEs) to act as the primary escalation layer for technical issues across our platform. You'll own the investigation, reproduction, and - where applicable- agent-assisted fix implementation that turns noisy customer reports into validated, high-signal work, so Engineering only receives production-ready problems for final review.

This is a hands-on, high-ownership role for people who love digging into hard problems with real diagnostic tools, who care about getting to the root cause rather than just clearing a queue, and who want their investigations to directly protect platform reliability for hundreds of thousands of healthcare workers and the facilities that depend on them.

What you'll do

• Monitor escalation channels and the Technical Support queue in Zendesk, catching early signals of systemic problems before they reach customers
• Investigate complex product, platform, and data-layer issues using tools like Datadog, internal dashboards, and SQL, reproducing bugs and producing evidence-backed escalations to Engineering.
• Handle live incidents end-to-end, from detection to closure: React to an incident with urgency, coordinate across Support, Engineering, and Product, and keep stakeholders updated with clear, structured communication
• Implement fixes where appropriate, testing your changes before handing off to Engineering for final review and sign-off
• Perform Root Cause Analysis and post-incident reviews, translating each issue into learnings that reduce recurrence and improve monitoring
• Maintain operational workflows (geofence, facility quizzes, NFC) accurately and quickly while spotting trends for prevention
• Capture investigative learnings in clear troubleshooting guides and documentation, and submit structured proposals that turn recurring patterns into actionable improvements
• Uphold our values such as unreasonably fast, ownership, and uncomfortably high standards in every interaction

WHO WE'RE LOOKING FOR

• Technical Fluency - You're comfortable investigating issues with observability tools (e.g., Datadog), writing SQL to interrogate data, and reasoning about APIs, backend configurations, and feature toggles. You can tell the difference between a UI, data, and code-level problem.
• Diagnostic Rigor - Every investigation you produce is thorough, evidence-based, and reproducible. You rule out config and data causes before escalating, and your write-ups are clear enough for another engineer to pick up without rework.
• End-to-End Ownership - You own problems from first report to confirmed resolution, including stakeholder updates and follow-through, with no gaps between hand-offs.
• Composure Under Pressure - You stay structured and calm during live incidents, balancing speed with accuracy and communicating clearly when stakes are high.
• Adaptability & Prioritization - You juggle structured work (incidents, bugs, workflows) with unplanned high-priority requests without letting SLAs slip.
• Systems & Prevention Thinking - You treat every issue as a chance to learn, identifying gaps in monitoring, tooling, or process and proposing fixes that prevent recurrence.
• Fluent, professional-level English communication, both written and verbal.

NICE TO HAVE

• Experience with observability and analytics tooling (Datadog, Sentry, Snowflake, or similar)
• Familiarity with SQL and reading application logs
• Background in technical support, SRE, incident response, or a related engineering-adjacent function
• Exposure to AI-assisted coding/agent tooling
• Experience in Ops, Support, or CX environments at scale

HIRING PROCESS

• Application Review
• Skills Assessment via Case Study
• Case Interview with Tech Support Team Lead
• Interview with Head of Worker Experience

Important Note: Clipboard operates 24/7. Team members work 5 days within a 7-day schedule, including weekend availability. Shifts are assigned based on business needs.

Quick Note on Scammers

Clipboard would never ask you for money or your bank details to participate in our hiring process. Report any scammers impersonating the Clipboard hiring team members here https://forms.gle/SyGaxHFbon7Hg9fW6.