From Commodore 64 to Digital Transformation: A Software Journey

Written by: Brian Dawson

4 min read

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Learn more about Chad Wathington's software journey by listening to his conversation with Brian Dawson on Episode 82 of DevOps Radio.

Chad Wathington has come a long way since he wrote his first software program on a Commodore 64 when he was six years old. It was the start of an amazing software journey that would eventually land him at ThoughtWorks, a renowned technology consultancy that helped pioneer the agile software movement. 

Along the way, Chad benefited from some helping hands, including a corporate-sponsored program for Black and LatinX children designed to expose them to software development, and a special community-based program that introduced him to the world of computer science. 

“I always wanted to be a technologist,” Chad says. After a detour through Harvard, where he earned a BA in economics, Chad rediscovered his software roots and found his way to ThoughtWorks, where he served initially as product director and now as chief strategy officer. 

“I've been able to dabble in a lot of different things over the last 15 years at ThoughtWorks,” Chad says. In his current role, Chad helps the company execute its strategy, deliver value to clients, and scale its service offerings. “Instead of just talking about digital transformation, we really help people with the technology, people and process to make that transition real,” he says.

A Software Journey With Roots in Agile

In its early days, ThoughtWorks made a name for itself rescuing client projects that had gone awry. “Someone would mess up on an application and ThoughtWorks would come in and help fix it,” he says. “That was our early bread-and-butter.” 

No wonder the first generation of ThoughtWorks employees was obsessed with engineering practices and figuring out a better way of working. “We created an ethos and culture around thinking about how to build software well.” It was a culture that attracted many of the leading lights of the fledgling Agile movement. People like Jez Humble and David Farley, authors of the landmark book Continuous Delivery

Their book “really changed the conversation,” Chad says. “It gave us the intellectual underpinning for understanding what we now know are some of the best ways to build software.” It showed that working in small batches, integrating on a continuous basis and deploying early and often can dramatically improve team productivity. 

Shortening feedback loops

Another thing continuous delivery showed was that it could speed up customer feedback. “DevOps gave developers and ops people a way to get fast feedback about what's working and what’s not,” Chad says. “Now they had a fast way to see their results and adjust.” 

Ultimately, such feedback loops are great for customers and end users. DevOps allows you to optimize all along the development path, he explains. It not only answers questions like “does this work in production?” but more importantly, “does it actually help solve the user’s problem and are they willing to pay for it?” 

In other words, while DevOps lets you move fast, it’s not just for the sake of speed, but to help you quickly hone in on what matters to the customer. “You may have a brilliant idea that you think may help you win in a marketplace, but you might be wrong,” he says. “If you don't build the feedback loops, you'll never know.”

Ethics in Technology

Chad is keenly aware of the broader social issues enveloping the tech industry. “There is change afoot and we have to do better,” he says. “We are building the core of society in lots of ways. Tech intersects with everything.”

He urges people to think holistically about the industry. It’s about more than just using technology to solve any given business problem, he says, but also about “asking whether we’re making the right technology at the right time to solve the right problem.”  

For Chad, this doesn’t mean you shouldn’t solve your immediate customer issues. It’s that you should also bear in mind the downside effects of technology and whether you’re doing your best to mitigate them. “Our place as technologists is not just to react but to be proactive in saying what we want the world to look like,” he says.

Today, Chad’s software journey continues to take him new places. His job no longer requires him to write code, but he likes to keep his toe in the waters he first dipped into when he was a small boy. “I still code on my own time,” he says. “I teach my kids how to code. Now it's for fun – and it keeps me grounded in the technologies that are moving our industry forward.” 

Listen to more of Chad’s story on Episode 82 of DevOps Radio.


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