Job Overview
Location
Canada - remote
Job Type
Full-time
Category
Customer Support
Date Posted
April 22, 2026
Full Job Description
đź“‹ Description
- • Senior Tier 2 Technical Support Specialist role focused on resolving complex technical issues across APIs, SaaS platforms, and cloud infrastructure while acting as a bridge between customers and internal teams.
- • Day-to-day responsibilities include diagnosing and resolving complex technical issues, triaging and escalating to engineering, improving support workflows and tooling, mentoring team members, and driving product feedback from recurring technical patterns.
- • Rewind AI, Inc. is a fast-growing Canadian startup backed by top-tier investors, specializing in cloud data backup for platforms like Jira, GitHub, Confluence, and Shopify, with a culture centered on teamwork, performance, customer centricity, and innovation.
- • In this role, you will deepen your expertise in SaaS support systems, develop technical leadership skills, influence product improvements through customer insights, and gain experience in incident response and AI-enhanced support tooling.
🎯 Requirements
- • 4–7+ years in high-complexity technical support, solutions engineering, or similar SaaS environment
- • Strong troubleshooting skills across web applications, APIs, and third-party integrations with 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) 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 ability to explain complex technical issues clearly to both technical and non-technical audiences
🏖️ Benefits
- • Flexible work hours
- • Employee stock options
- • Health benefits
- • 3 weeks vacation
- • 7 life leave days
- • 2 Level Up days for professional development
- • $2000/year wellness/home office allowance
- • $5000/year professional development allowance
Skills & Technologies
About Rewind AI, Inc.
Rewind AI, Inc. provides desktop software that records and indexes everything a user sees, hears, or types, creating a searchable memory of their digital activity. The application runs locally, encrypts data, and enables users to retrieve past meetings, documents, websites, and conversations through natural-language queries. It integrates with macOS and iOS, supports optical character recognition and audio transcription, and offers AI-generated summaries and action items. Targeted at professionals and teams, the tool aims to enhance productivity, reduce note-taking, and minimize context switching by preserving and surfacing relevant past information on demand.
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