[Hiring] Senior Tier 2 Technical Support Specialist @Rewind

Role Description

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.

What you’ll do

• Technical troubleshooting & resolution
  • 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 to reason about problems before reproducing 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.
• Escalation management & engineering collaboration
  • 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.
• Support systems & tooling optimization
  • 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.
• Mentorship & technical leadership
  • Raise the bar for the team through hands-on mentorship in debugging, writing, and customer communication.
  • Contribute to onboarding and training for new hires.
• Customer insights & product feedback
  • 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.

Qualifications

• 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.

Requirements

• 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.

Location and working hours

• This is a remote role within Canada with a strong preference for candidates located in Ottawa or Vancouver area.
• Working hours are typically 9am–5pm local time, with occasional adjustments for incident response or coverage, including evenings, weekends, and holidays as needed.

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.

Why join Rewind

At Rewind, you’ll help shape the future of data protection for thousands of businesses. We’re performance-driven, innovative, and not afraid to challenge what’s possible. You’ll join a team that values trust, accountability, and respect for people’s time — and encourages every employee to experiment, think critically, and grow.

AI Usage

Our recruitment process may include the use of artificial intelligence–enabled tools to help manage and review applications efficiently. These tools assist our team, but hiring decisions are ultimately made by human reviewers.