Senior Tier 2 Technical Support Specialist

Rewind

1d•Remote

About The Position

We’re looking for a Senior Tier 2 Technical Support Specialist to help our customers navigate complex technical challenges with confidence. You’ll go beyond surface-level troubleshooting-diving into systems, integrations, and edge cases to find solutions while leveraging modern AI tools to improve the overall support experience. In this role, you’ll act as a bridge between customers and internal teams, translating technical issues into actionable insights and helping scale a highly capable, AI-forward support function.

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

Nice To Haves

A Computer Science background or equivalent technical experience in a fast-paced SaaS environment
Ability to read and navigate Ruby on Rails application architectures and background job systems (e.g., Sidekiq)
Experience supporting backup, data recovery, or data migration systems
Familiarity with SaaS ecosystems such as Shopify, QuickBooks, GitHub, or the Atlassian suite
Experience with platform-specific tools such as the Shopify Partner Portal, Stripe, or SendGrid
Familiarity with cloud infrastructure and observability tools (e.g., OpenSearch, New Relic, Honeybadger)
Basic scripting ability (e.g., JavaScript, Python) for debugging or automation
Experience building or improving workflows using tools like n8n, Zapier, or AI-assisted development tools (e.g., Claude Code, Cursor)
Experience mentoring or guiding team members in advanced troubleshooting and structured problem-solving

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.