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Reliability Engineer

May 27, 2026

Chelsea Avondale is the world’s most cutting-edge home insurance group. We have developed sophisticated risk modeling and insurance pricing technologies for home insurance and deploy that technology through our own insurance company. Our team consists of some of the brightest minds in insurance, software development, finance, and operations. Our group includes our scientific research & engineering division (Skynet Software) and Canadian property & casualty insurance company (Max Insurance). Together, our group is transforming the Canadian and global insurance landscape. JOB DESCRIPTION: Chelsea Avondale is looking for a Reliability Engineer with a background in infrastructure system engineering to support the growth of a secure, dynamic, and scalable IT environment across the group. Our business is going through rapid growth, and it is essential that our systems infrastructure keeps pace. The Reliability Engineer will play a crucial role in ensuring the reliability, scalability, and performance of our systems, enabling the continuous delivery of our products and services. They will be accountable for ensuring overall availability, as well as enhancing Engineering teams’ capability to design, build and operate robust systems at scale. This position is ideal for candidates who have an extraordinary sense of responsibility and are not afraid to roll up their sleeves. Our IT environment is not toolkit rich. What we are NOT looking for is someone who wants to take months installing a large number of tools from their preferred toolkit. We take pride in maintaining a fundamental stack of technologies, much of it in Python, and we are looking for someone who shares this mentality. If you are someone who thrives in a high-performance culture and is eager for work that is both challenging and constantly evolving, this role is perfect for you. We strongly encourage and help our team members to improve and enhance their personal skill sets within our organization. On your journey with us, you will have the ability to learn and grow rapidly, taking on more responsibilities. RESPONSIBILITIES: <ul> <li>Play an integral role in the design, implementation & maintenance of AWS cloud server environments.</li> <li>Design, implement, and maintain robust monitoring and alerting systems in Python to detect and respond to incidents in a timely manner.</li> <li>Collaborate with cross-functional teams to enhance reliability of our systems and services.</li> <li>Design, configure, deploy, and maintain infrastructure on AWS using best practices and industry standards.</li> <li>Conduct post-incident analysis to identify root causes, implement corrective actions, and prevent similar issues in the future.</li> <li>Assist in capacity planning & optimize services to provide scalable, stable, & secure systems.</li> <li>Implement high availability and disaster recovery solutions to provide data redundancy, resilience, and data loss prevention.</li> <li>Assist with the implementation of select network engineering solutions including firewalls, load balancing, VPNs & LANs, where necessary.</li> </ul> PREFERRED EXPERIENCE & SKILLS: <ul> <li>Bachelor’s degree in Computer Science, Computer Engineering, Electrical Engineering, or related field.</li> <li>1+ years of experience as a Reliability Engineer or similar role, with a focus on maintaining high-performance, scalable, and reliable web systems.</li> <li>We also encourage highly motivated new grads to apply.</li> <li>Hands-on experience with AWS cloud environments – instances, CloudWatch, EFS, etc.</li> <li>Proficiency at Python is a must.</li> <li>Experience using NGINX for reverse proxy, load balancing, and caching.</li> <li>Experience with Unix / Windows server configuration, administration, performance tuning and troubleshooting.</li> <li>Working knowledge of web technologies (web servers, DNS, SSL, Browsers).</li> <li>Working knowledge of web development processes (source control, deployment, etc.).</li> <li>Experience load testing, pen testing, and providing security for cloud resources is beneficial.</li> </ul> Skynet Software welcomes and encourages applications from people with disabilities. Accommodations are available on request for candidates taking part in all aspects of the selection process.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...