Tech Debt Burndown Podcast Series 2 E3: Jamie Dobson

Posted on Tuesday, Mar 21, 2023
Nick and Chris talk to Jamie Dobson.

Show Notes

Recording date: Apr 1, 2022

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“When you frame technical debt through the lens of strategy, it actually starts to make a lot more sense” - Jamie Dobson

With intros over we ask Jamie about his experience with cloud native transformation. He sees many companies who have made a mess of their cloud migration. They have created a lot of technical debt, which can make it difficult to innovate and can lead to security problems.

Jamie says that the best time to do a do over is when you realize that your cloud migration is not working. However, he acknowledges that this is a difficult decision to make. People often feel like they have invested too much time and money in their current system to change it. However, it is often better to start over than to continue down a path that is not working.

Jamie then talks about how to approach cloud native transformation from a strategic point of view. He says that it is important to understand the company’s goals and objectives before making any decisions about cloud migration. Once you understand the company’s goals, you can then start to think about how cloud native computing can help you achieve those goals.

Jamie concludes by saying that cloud native computing is a powerful tool that can help companies to innovate and grow. However, it is important to approach cloud native transformation in a strategic way in order to get the most out of it.


Jamie Dobson

Jamie Dobson

Jamie Dobson is co-founder and CEO of Container Solutions, a professional services consultancy specializing in cloud migration. A first encounter with a BBC computer and BASIC at the age of nine launched a lifelong passion for programming and software development. He eventually developed a matching passion for coaching and organizational strategy to help humans work effectively and beneficially with the technology that increasingly drives our lives.


Chris Swan

Chris Swan

Chris is a frequent speaker on topics such as serverless, DevOps, cloud, containers, security, networking and the Internet of Things. He’s also a cloud editor for InfoQ and a contributor to open source projects such as Docker, CoreOS and DXC’s Online DevOps Dojo.

Nick Selby

Nick Selby

Nick is Vice President of Assurance at Trail of Bits. He was formerly Chief Security Officer at a financial technology firm. Prior to that he was Director of Cyber Intelligence and Investigations at the New York Police Department. He is co-author of many books, including Cyber Attack Survival Manual; In Context: Understanding Police Killings of Unarmed Civilians and Blackhatonomics: An Inside Look at the Economics of Cybercrime.