Matt Crampton shares lessons from 25 years in tech, on innovation, adaptability, and the journey from development to CTO.
When you think about the rise of the gig economy, platforms like Uber or DoorDash may come to mind. But years before those apps took off, Matt Crampton was already helping to pioneer flexible, on-demand work.
In our recent episode of Byte Happens, our host, Flavia Taborga, sat down with Matt to reflect on his journey, from tinkering with a Tandy 1000 as a teenager to leading engineering teams at AOL and Yahoo, and co-founding startups that have shaped entire industries.
Matt’s love for tech started in high school, when he ran a bulletin board system on his Tandy 1000—long before the internet became mainstream. That curiosity led him to co-found the Kalamazoo Linux Users Group in the late ’90s, and soon after, a role at Netscape/AOL.
His move to Silicon Valley opened doors to AOL and later Yahoo, where he worked on large-scale consumer products and saw firsthand how the internet was reshaping the world.
In the early 2010s, Matt co-founded GigWalk, a marketplace where 1.2 million “gigwalkers” performed micro-jobs via their smartphones. From photographing restaurants for Microsoft’s Bing Maps to checking retail displays for Pepsi and Red Bull, GigWalk demonstrated the power of crowdsourced work.
After GigWalk, Matt turned his attention to legal tech. With co-founders Sarah and Thornton Schaaf, he built Headnote, a payment solution designed specifically for law firms to handle trust accounting compliance.
At a time when most lawyers still relied on paper checks, Headnote introduced digital payments while ensuring compliance with strict U.S. regulations. The company was later acquired and now powers payments across multiple practice management platforms under Paradigm.
One of the biggest challenges Matt faced was transitioning from engineer to manager. Startups require founders to wear both hats—coding and leading—until the company reaches a certain level of growth. “At some point, you realize you can’t do both. Managing people is a whole different skillset,” he reflects.
For Matt, learning to ask for help, lean on his network, and nurture leadership in others has been key to scaling teams and companies.
Today, as Sr. Director of Engineering at Paradigm, Matt continues to develop technology that empowers legal professionals while collaborating with distributed engineering teams worldwide.
His story is a reminder that timing, adaptability, and a willingness to say “yes” to new opportunities can shape a career in unexpected ways.
Want to hear the whole conversation with Matt Crampton? Watch the episode of Byte Happens here.
You can follow Matt at:
Website: https://www.mattcrampton.com/
LinkedIn: http://www.linkedin.com/in/mattcrampton
Tune in to Byte Happens and explore the human side of technology with the pioneers shaping our digital future!
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