Technical Support Engineer

DevelopmentFull TimeOttawa, ON

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"Customer service is an attitude, not a department." - this is not our quote, but we love it.

Rewind is looking for a Technical Support Engineer to help our Tier 2 Support team provide the best customer service in SaaS. 


On Tier 3 Technical Support, you’re the last line of defence. Tier 2 Support looks to you when faced with a customer problem they can’t solve. The most difficult, complex issues are no match for your skills. You are the subject matter expert on how our products actually work.

Communication is equally as critical to this role as technical knowledge. You must be able to communicate effectively, regardless of your audience – in addition to connecting directly with our customers, Tier 3 Technical Support liaises with many other teams to resolve issues; being able to empathize with others, manage multiple communication styles and technical knowledge as needed, on the fly, is an essential asset.

You will work closely with Tier 2 Support as well as R&D in a variety of situations: from guidance to writing code. You must enjoy interacting, teaching, and collaborating with others.

You must stay on top of an ever-growing body of knowledge relating to our products and the platforms to which we integrate. You’ll be challenged to expand your knowledge and expertise on a daily basis! You must have a thirst for learning and information acquisition and possess the discipline to catalog this knowledge and expertise for the benefit of future yous that join your team.

You should be driven to be the best at what you do – but also enjoy being challenged by, and constantly learning from, the other members on our high-performing team.

You should have a love for problem-solving, troubleshooting, and tough puzzles – complex problems are your bread-and-butter! It can take hours, days, and sometimes weeks to get to the bottom of a real head-scratcher. You’ll need to be comfortable with finding short term work arounds for issues that ultimately require lengthy time and effort to resolve.

You need an observant eye for details, whether it’s with code, spelling, or something else entirely. Prove it to us – address your cover letter to Ms. Rails. You are going to pore over logs, database entries, and code on a regular basis, and it’s often the smallest things which can make or break an investigation.

To give you a better sense of what you’ll be doing day to day, here are some of the issues we’ve dealt with recently:

  • Recovering from the impact of a BigCommerce webhook outage.
  • Identifying the root cause of and recovering from an OAuth token refresh failure that impacted backup service for over 200 customers.
  • Helping an e-commerce customer revert accidental changes to a subset of orders.
  • Diagnosing a billing anomaly that prevented a small subset of our customers from paying us.
  • Squashing a software bug that was preventing the successful restoration of an e-commerce merchants terms of service pages.
  • Identifying an AWS miss-configuration that prevented the successful restoration of an e-commerce merchants product catalog.
  • Enhancing our backend administration tools to enable customer impersonation by our Tier 2 Support, allowing them to experience what our customers are experiencing.


You are a perfect match for this role if you’re someone who possesses great troubleshooting and analytical skills, you’re an exceptional communicator, you have prior experience troubleshooting or building Ruby on Rails-based applications, and you have a curious mind for how things work and what makes them tick.

Our Tier 3 Technical Support members are masters of our products - they know them from top to bottom and inside out - and they are regularly in the Rewind codebase solving obscure mysteries, fixing bugs, sharing their learnings, and providing ways to make supporting our customers better for everyone.

You should enjoy making complicated situations simple and painless. This means being a great problem-solver with the ability to process and resolve issues quickly. You should be a stellar communicator, even when you have to communicate less-than-stellar news. You should have highly tuned senses of compassion and empathy and a drive to constantly help others.

You must be proficient in REST and GraphQL APIs, JavaScript, HTML, CSS, SQL, Linux, and major browser development tools. You should be well-versed in AWS, source control management (preferably Git), and one of either Ruby or Python. 

You might have a CS degree. You might not. That’s not what we’re looking for. We care about what you can do and how you do it, not about how you got here. A strong track record of conscientious, thoughtful work speaks volumes.

You love supporting people. This isn’t a springboard into another area at Rewind. You want to be part of our support team for a while, and you’re excited to help thousands of customers along the way.

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


We pay at the 50th percentile of the industry for the matched role and experience, based on rates in Ottawa, Canada. We also offer stock options so that you can share in the success of the business.

We're looking for an intermediate or senior person for this role. The starting salary for an intermediate role is $88,000. The starting salary for a senior role is $105,000. We assess seniority relative to the team at Rewind during the interviewing process.

Our benefits are all aimed at supporting a life well lived away from work. None are about trapping people at the office or working endless overtime. Just the opposite. We’re all about reasonable working hours, sufficient vacation time, summer hours, fitness, wellness, food, education, and charity. See the full list.

If you want to join our team to help make our customers happy, please apply!


Be authentic, be yourself, be creative, and take your time with the application. We want to see your personality. There’s no prize for being the first to submit! Stock cover letters won’t do. Tell us about:

  • why you want to work in technical support.
  • why you want to work at Rewind and not somewhere else.
  • a description of a great customer service/support experience you had recently, and what made it great.
  • a time you taught yourself a new skill to complete a job or project.
  • describe the installation flow for installing Rewind into a trial BigCommerce or Shopify store.
  • a guide to making your favourite meal.

Then, pick two of the Tier 2 Support questions below and describe how you would approach the problem as you would if you worked here and compose a response as appropriate to the question. Hint: Make (and state) as many assumptions as you want. Be as detailed as you can. We value tone and style over correctness.

  • Customers are reporting that they can’t update their credit card because the page isn’t loading; can you look into what’s going on and get back to me?
  • An e-commerce customer is reporting that their products were restored without images; can you find out why and respond to the customer with details?
  • An e-commerce customer is saying we deleted all of their products; can you investigate what might have happened and get back to the customer?
  • An accountant is trying to add a third QuickBooks file to their Rewind account but they are getting an error; can you follow up with the customer and help them troubleshoot?
  • Customers are reporting a 502 error when trying to get to their vault, can you look into what’s going on and get back to me?
  • We are getting reports that people are changing their stores but those changes are not appearing in their vaults. Can you look into what might be happening and get back to me?

Experience comes in many forms, many skills are transferable, and passion goes a long way. If your background is close to what we’re looking for, please consider applying, even if you aren’t able to check every box above. We are dedicated to diversity and providing an inclusive workplace for all and especially encourage members of underrepresented groups to apply.

We’re seeking fluent English speakers/writers to work with us to help Tier 2 Support address customer and product issues via email, phone, and chat during these hours:

  • Monday through Friday 9am-5pm EST
  • Saturday and Sunday, 9am-5pm EST (only as needed)

Your location isn’t as important as your fit to the role. That said, we do prefer that your working hours fall within the North American timezones so as to provide as much overlap with our existing team and to ensure you aren't forced to work outside of regular daytime hours. If you are outside of Ottawa, don’t forget to tell us where you’re located!

After you apply, we’ll let you know that we’ve received your application. After that, you probably shouldn’t expect to hear back from us unless you’ve been selected for a screening call.

We look forward to hearing from you!