Summary
Thomas Willingham is a technology leader with a decade of experience building and scaling commercial platforms, currently overseeing Professional Services, GTM systems, automation, and AI across Square, Cash App, Afterpay, and Clearpay at Block. He combines hands-on engineering roots in Python, C, and web design with cybersecurity and compliance savvy from roles spanning senior software engineer to head of global partner and merchant services. Thomas has a track record of moving between product, infrastructure, and customer-facing technical teams to drive onboarding, solution engineering, and technical account management at global scale. He runs his own consultancy, Willingham Digital, and previously served as CTO at Simpeo, showing an entrepreneurial bent alongside enterprise leadership. Based in San Francisco, he pairs a B.Sc. in Computer Science with executive business training, enabling him to translate technical complexity into repeatable commercial outcomes. A pragmatic operator, he often blends automation and AI to accelerate GTM and support workflows behind the scenes.
10 years of coding experience
16 years of employment as a software developer
Executive Master of Business Administration, Executive Master of Business Administration at Quantic School of Business and Technology
Bachelor of Science (B.Sc.) Computer Science, Bachelor of Science (B.Sc.) Computer Science at The University of Alabama