Stephen Winter is a pragmatic technology executive with nine years of experience scaling digital platforms and leading large global engineering organisations, currently serving as CTO of Staysure Group in Queensland. He has progressed through roles from solutions and enterprise architect to Managing Director of Technology, combining hands-on engineering (Java, cloud, CI/CD) with strategy and AI-led transformation. Stephen has repeatedly delivered high-traffic, mission-critical payments and banking systems—most notably leading Tesco Pay+ technical delivery where the digital wallet processed transactions every 1.5 seconds at scale. He is skilled at translating C-level strategy into operational engineering practices and has run global teams of 300+ while still engaging with low-level technical design. His academic background in Advanced Security and Digital Forensics (GCHQ-endorsed) underpins a strong security mindset across architectures and integrations.
9 years of coding experience
13 years of employment as a software developer
Bachelor of Science (BSc) BSc Computer Science, Bachelor of Science (BSc) BSc Computer Science at London Metropolitan University
Master’s Degree Advanced Security and Digital Forensics (Endorsed by GCHQ), Master’s Degree Advanced Security and Digital Forensics (Endorsed by GCHQ) at Edinburgh Napier University
Contributions:1 release, 51 pushes, 1 branch in 2 years 5 months
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Stephen Winter - Chief Technology Officer at Staysure Group