Senior Tier 2 Technical Support Specialist

Rewind is a service that protects the critical data that powers businesses of all sizes. Our focus is on backing up data that lives in the cloud - in apps like Jira, GitHub, Confluence and Shopify. We are backed by Insight Partners, Inovia, Bessemer and Atlassian Ventures and are proud to be recognized as one of Canada's 50 fastest growing technology companies (2023 Deloitte Fast 50). We invite you to read our startup story to learn where we came from and where we’re going.

Read about our mission, story and values here.
To find out more about our perks, click here.
Some of our Blogs might help you get a better understanding of what we do here. You can find them all here.

Thriving at Rewind:

We embrace the fast-paced, ever-changing nature of startup life. If you love working with speed, agility, and creativity, you’ll feel right at home here. Here's what it takes to succeed with us:

• Team-First Mentality: We put teamwork at the core of everything we do, believing that we are better when we are together. Success is shared, and when the team wins, we all win.

• Performance-Driven Mindset: We are proactive, goal-oriented, and focused on delivering tangible, high-quality results. We go beyond meeting expectations - we aim to exceed them.

• Flexible Work-Life Approach: We encourage balance and understand the need to recharge. While we stay agile for urgent needs, we make sure there's time to recover and enjoy life.

• Customer Centricity: Our commitment to customers shapes everything we do. We listen, build relationships, and innovate - from our dedicated customer support team to our engineers, everyone at our company is focused on solving problems that matter most to our users.

• Taking Initiative: We value ownership and proactive problem-solving. We encourage team members to think creatively, take ownership, and lead improvements. Your ideas and actions drive our success.

• We Make Time for Fun: We work hard and make time to enjoy the journey. It’s not just about hitting milestones—it’s about making the experience rewarding along the way.

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 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

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.

• 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

• 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

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.

Compensation Philosophy
The actual base salary will vary based on various factors, including market and individual qualifications objectively assessed during the interview process. The listed range above is a guideline, and the base salary range for this role may be modified.

If your expectations are above this range, it may be because your experience aligns with a more senior level. In some cases, we’re open to hiring at a higher level for the right person and are committed to paying competitively and fairly.

If your experience is closer to an earlier career stage, we may still consider your application. In that case, we would evaluate the role at a different level within our levelling framework, which would correspond to a salary below the range shown.

Pay is just one part of the overall compensation at Rewind.

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.

We support innovation through experimentation — including smart use of AI tools — and believe the best ideas come from those who aren’t afraid to push boundaries.

How Rewind Will Support You
We know that enjoying the journey is just as important as reaching our goals. We work hard to create a positive, inclusive environment where fun and laughter are part of our everyday routine. We also offer a variety of benefits to support your success both at work and in your personal life which includes but is not limited to: 

• 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

Rewind is committed to building an inclusive, supportive place for you to do the best and most rewarding work of your career. We value how each new hire is an opportunity for us to bring in a different perspective, and we are always eager to further diversify our company. We strongly encourage candidates of all different backgrounds and identities to apply.

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.