Leaders in Tech: Barry Dawson

Welcome to the next feature of our Leaders in Tech editorial series. Speaking to leaders in the industry to capture their stories, career highs and lows, their trials and successes, their current company and their role, most recent projects, advice to others, and the individuals who they most look up to in the industry.

Today, we talked to Barry Dawson, Release Manager at Gore Mutual Insurance, to find out more about why he joined the tech industry, what his role entails, what are the challenges he faces, and his advice to aspiring engineers and testers.


First of all, can you tell me a bit about yourself and your current role?

My name is Barry Dawson and I am the Release Manager at Gore Mutual Insurance. Outside of work, I am always active. I have always played sports and I build an ice rink at my house almost every year. I coached competitive girls’ soccer (for my daughters) for close to 20 years. I am passionate about health & wellness, I have followed a mainly vegan diet for the last 8 years. I started home DIY projects with our first house and have grown that into a side business recently flipping houses.

I also sit on the board of directors for a not-for-profit Long Term Care Home.

How did you get to where you are now?

I started my career in retail management. I took Retail Management at Sheridan college while working at Eaton’s. I started as a retail management trainee immediately after completing school and quickly moved through multiple levels of Sales Manager and worked in 4 stores over 5 years. I was fortunate to be at the turning point for technology in retail at this time and I became an early adapter in using the technology available. This led to an opportunity to join HR as a Systems Trainer, which, in turn, led to becoming a systems training specialist where I was responsible for creating the training & training packages to then train the trainers.

At the time Eatons shut down, I believed that I was an expert in technology. I was a Guru in Microsoft Office and for all the business applications that I created training for, so I looked for opportunities to utilize my expertise. I got the opportunity to join Sears as a Business Analyst, it was only then that I realized how much I actually did not know about technology, and how much more there was behind the scenes. This drove my passion to learn even more and I read and referred to the Business Analysis Body of Knowledge (BABOK), took Business Analysis related training, and attended Business Analysis and PM conferences, as well as taking night courses on programming and Microsoft Certified Systems Engineer (MCSE).

This opened the opportunity to become a Technical Analyst for Retail systems, then a Programmer Analyst in Infrastructure services where I became a hardware & Network SME and then Citrix and VMWare administrator. I was strongly encouraged to become a manager for the infrastructure services team that I was a part of. This was a great opportunity so I agreed even though I did not want to move away from my newfound passion for application and hardware virtualization.

Within a couple of years, I was asked to take over the Desktop and application support teams where I had the opportunity to learn and participate in hardware and software licensing, including procurement and creation of contracts and Statements of Work for vendors and Enterprise agreements. An opportunity then arose to move into a shared technology & business role to act as a business liaison and help the business and technology groups understand each other’s needs and bridge the gap between them. It was always a great way to learn and expand my understanding of business and technology.

Shortly after taking this role, I was asked again to change roles to fill a need and become a Project Manager for Retail POS, Reporting, and Dealer store technologies, as there were significant challenges in the relationship between Technology and Dealer businesses. During this time I was often referred to by my boss as his technology Swiss-army knife and often asked to chair and host technology meetings for the business as I would be the one that could get business onboard and could deliver not so good news in a way that we could turn things into opportunities to do better.

I was encouraged by a close friend to apply for a role at BMO. This was a great opportunity to expand my background to include a financial Institution, and take on the challenge to Oversee Application Development as an Application Software Development Manager. This role included some application currency and application support responsibilities and again, introduced a whole new world of technology and processes.

As things often do in technology, areas shift and reorganize making my previous role obsolete… This led me to become a Test manager, which was a bit of a shock! Although I had some reservations as I had not done this before, I knew that I always enjoyed the learnings and grew from each experience. Indeed, I learned to admire the hard work and perseverance that my team had while dealing with the pressure of Business & PMO & senior management at the crunch of each release, however, I did not excel in this role. I found myself caught between the best interest of my staff and the demands placed on us. I decided to take another role in the organization and it so happened that it was a Test Lead role on enterprise-wide technology implementation.

I welcomed the opportunity to step back and take a role where I could challenge and focus on my own contribution. I had only recently started to look at things from a testing lens, but now looking at them from a test planning perspective, everything changed. I thoroughly enjoyed the opportunity when I realized that I was able to use almost all of my background experience, such as the technical writing experience from my time as a Training Specialist writing and publishing training, the Business Analysis capabilities to write and understand/translate requirements, and the process & software development experience of understanding software development. I also enjoyed the benefits such as being able to build a solid relationship with areas like infrastructure and release management with planning and scheduling of environments.

This led to another great role within BMO where I was offered Head of Testing for one of the core business areas with both onshore and offshore resources of close to 100 Leads & Testers. I am very proud of being able to help many Test Leads with their careers and being able to mentor and coach Testers.

Next came an opportunity to leave the financial industry and join WSIB in the Insurance industry as a Test Manager. This role was offered to me by the same manager that gave me the Head of Testing at BMO opportunity. I had the opportunity to grow the testing organization and transform it into a QA-COE. We were able to do this in under three years and I & my co-managers & director were awarded the “Best Management Team of the Year” at the North American Software Testing and QE Awards 2019.

Early in 2020, the Information Technology group at WSIB made changes and the QA management team were no longer needed there. I found myself at the very beginning of COVID with not a lot of demand. Thankfully, I was very fortunate to have the possibility to look at options and try new things outside of my technology life, to have a new way to spend my time.

I also accepted the offer to join a board of directors at a not-for-profit Long Term Care home in Georgetown during the start of 2020. This led to providing some business and technical consulting followed by chairing a redevelopment committee that was successful in our application to build a much larger new home and I now sit on the Executive committee in addition to chairing the development committee and sitting on the board of directors.

And now, I very recently decided to look for new opportunities to get back to technology in a contract and/or consulting capacity. I started my first 1-year contract with a fast-growing insurance company as a release manager with the goal to build a solid release management practice to support the company’s growth initiatives.

I am excited to see how I can add the skills and knowledge of Quality Assurance & Quality Excellence (QE) to my new adventure.

What inspired you to get involved in the IT industry?

Seeing the value of technology in the day to day business activities.

Why did you decide to specialize in QA and Testing?

I fell into it. I love driving changes that significantly improved the overall time to test and quality.

Do you have a favorite part of your job? 

The sense of accomplishment! For instance, zero sev 1 or 2 defects into production.

What are some of the challenges you faced during your career?

The most challenging was being a boss that had Dev and QA under their responsibilities, and I felt like the roadblock to their success.

How do you keep your team motivated despite conflicts?

By being a ‘glass half full’ person!

What are you the proudest of in your career so far?

Winning the “Best Management Team of the Year” at the North American Software Testing and QE Awards 2019.

Do you have any advice for aspiring testers?

Don’t be afraid to try new things!

Finally, do you have a memorable story or anecdote from your experience you would like to share with us?

The most impactful and valuable thing that has happened to me had little to do with any job or role in my career, it was the opportunity that I was given to join a Peer Support group at WSIB. This was a complete volunteer opportunity to learn how to support peers (co-workers). I became a senior peer support member and that allowed me to work with and coach peer support, team members. I have never had such a rewarding feeling or purpose and can’t say enough how this impacted me in my own personal life in such a positive way!