Support Engineer troubleshooting complex API, integration, and production incidents for OpenAI’s Premium Support customers. Improving reliability through monitoring, runbooks, automation, and postmortems.
About the role
- Senior Tier 2 Technical Support Specialist helping customers navigate technical challenges at Rewind. Responsible for troubleshooting, escalation management, and optimizing support workflows.
Responsibilities
- Diagnose and resolve complex technical issues across APIs, SaaS platforms, and cloud infrastructure.
- Identify systemic failure patterns across tickets and drive changes that prevent entire categories of issues.
- Build a working mental model of Rewind's architecture and integrations so you can reason about problems before you reproduce them.
- Reproduce bugs, analyze logs, and identify root causes to drive effective solutions
- Communicate technical concepts clearly to both technical and non-technical customers
- Actively participate in incident response and help define the framework for a future 24/7 on-call rotation as we scale our support coverage
- Triage and escalate issues to Engineering with clear documentation and reproducible steps
- Partner with Product and Engineering to prioritize and resolve defects
- Act as a technical liaison, ensuring customers are kept informed throughout resolution
- Improve workflows, automations, and support tooling to increase efficiency
- Build and maintain internal runbooks and troubleshooting guides
- Identify opportunities to reduce ticket volume through proactive fixes and self-serve resources
- Raise the bar for the team through hands-on mentorship in debugging, writing, and customer communication
- Contribute to onboarding and training for new hires
- Recognize recurring technical issues, document the pattern, and recommend product or infrastructure improvements
- Partner with internal teams to advocate for scalable, customer-centric solutions
- Drive excellence through the continuous evolution of Rewind's technical support frameworks.
Requirements
- 4–7+ years in a high-complexity technical support, solutions engineering, or similar environment in a SaaS organization
- Strong troubleshooting skills across web applications, APIs, and third-party integrations, with the ability to isolate root causes across system boundaries
- Hands-on experience diagnosing issues across REST & GraphQL APIs, webhooks, and authentication methods (OAuth)
- Proven ability to debug data discrepancies, including identifying gaps between expected and actual data in API-driven systems
- Strong ability to read and interpret production logs and metrics (e.g., AWS CloudWatch or similar) to identify root causes prior to escalation
- Proficiency using tools like Postman, curl, or similar to reproduce and investigate API issues
- Working knowledge of SQL or similar query languages for data validation and troubleshooting
- Proven experience in incident management, including participation in high-severity or on-call rotations
- Strong written and verbal communication skills, with the ability to explain complex technical issues clearly to both technical and non-technical audiences
- Demonstrated ability to operate with urgency during data-risk events while maintaining structured, methodical problem-solving.
Benefits
- Flexible work hours
- Employee stock options
- Health benefits
- 3 weeks vacation
- 7 life leave days
- 2 Level Up days for professional development
- 1 volunteer day
- Summer Fridays and office closed during the holiday break in December
- Paid parental leave
- $2000/year wellness/home office allowance
- $5000/year professional development allowance
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