Senior Technical Support Engineer

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.

The Senior Technical Support Engineer (T3) is the highest tier of our support organization, serving as a bridge between customer support and engineering. You will own the most complex, ambiguous technical escalations that our T1 and T2 teams cannot resolve - including issues that previously required involvement from the Engineering Run Team.

As the most senior member of the support team, you’ll also be its on-the-floor leader. You’ll make judgment calls, coach T1/T2 through tough situations, and help build this new tier from the ground up.

The Role

As a Senior Technical Support Engineer, you will serve as the final escalation point within the support organization. You bring a software development background and deep technical instincts to diagnose root causes, reproduce edge cases, write or read code to understand issues at depth, and work directly with the Engineering team to drive resolution. This is not a traditional support role - you will spend a significant portion of your time doing technical investigation work that sits at the boundary of support and engineering.

This role requires participation on a on-call rotation including weekends and holidays.

What You'll Do

• Own the most complex technical escalations from T1 and T2, serving as the final line of defense.

• Investigate and reproduce customer-reported bugs, data inconsistencies, and integration failures across Rewind's supported platforms (Jira, Confluence, GitHub, Shopify, QuickBooks Online, and more)

• Read and write code (primarily in the context of debugging and scripting) to diagnose issues, test hypotheses, and validate fixes

• Work directly with Engineering to clearly articulate bugs, provide reproducible test cases, and track fixes through to resolution

• Manage and resolve issues in customer environments involving API integrations, OAuth configurations, webhook failures, and platform-level permissions

• Handle data restoration requests and complex recovery scenarios requiring deep knowledge of Rewind's backup architecture

• Give direct, constructive feedback to T1/T2 team members when an escalation or error needs a course correction

• Lead blameless postmortems that separate process gaps from individual coaching needs, and recommend clear options (training, process changes, guardrails)

• Mentor and upskill T1/T2 through pairing, lunch-and-learns and escalation reviews, and set the bar for what a well-prepared escalation looks like

• Help define the processes, SLAs and ways of working for Rewind’s new Enterprise Support tier as we build it from scratch

• Own enterprise customer onboarding when required, including installation, deployment, and education, ensuring the customer is fully set up for success

• Help build and maintain the internal knowledge base for complex issue patterns, enabling T1/T2 to self-serve future resolutions

• Participate in on-call rotations for P1 incidents affecting enterprise customers

• Identify recurring escalation patterns and proactively surface product improvement opportunities to Engineering and Product

What You Bring

Required

• 5+ years of experience in a technical support, solutions engineering, or software development role

• Demonstrated informal leadership: you’ve mentored teammates, given peer feedback, or acted as the go-to senior person on a support or engineering team

• Computer Science degree or equivalent practical experience (you can read and write code)

• Proficiency in at least one scripting or programming language (Python, Ruby, JavaScript, or similar)

• Strong understanding of REST APIs, OAuth, webhooks, and modern SaaS integration patterns

• Experience with cloud platforms and SaaS ecosystems (Atlassian, GitHub, Shopify, or similar)

• AWS - CloudWatch for logs, OpenSearch/Kibana for search infrastructure, SQS/SNS for async processing

• Ability to read logs, inspect API responses, and debug issues at the network and application layers

• Exceptional written and verbal communication - you can explain a complex technical root cause to a non-technical customer and to an engineer on the same day

• Comfort working independently in ambiguous, high-stakes situations with limited documentation

Nice to Have

• Experience with backup, recovery, or data resilience products

• Familiarity with Jira, Confluence, or Atlassian platform administration

• Experience with PostgreSQL and DynamoDB

• Prior experience in a SaaS company at a similar scale (Series B / growth stage)

• Experience working with enterprise customers and navigating complex account relationships

• Experience as a team lead, senior or staff support engineer, or escalation lead

Location

There is a strong preference for candidates based in Ontario for easier collaboration.

Compensation Philosophy
The actual base salary will vary based on various factors, including market and individual qualifications objectively assessed during the interview process.

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.

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.