Chief Technology Officer

Stephen Winter

Brisbane, Australia

Technology executive with deep expertise in software development, architecture, and engineering leadership across Financial Services and Retail — operating at significant scale for some of the largest organisations in the UK and Australia. An executive who still writes code, staying hands-on with emerging technologies to maintain technical depth and credibility with engineering teams.

Stephen Winter - Chief Technology Officer
14+
Years in Tech
400+
Team Size Led
3000+
Stores Served
Still Codes

Experience

Staysure Group

Chief Technology Officer

January 2025 – Present
  • Responsible for all Group technology (~400 headcount) within a regulatory environment, including offshore development, support and modernisation of the technology landscape.
Staysure Group

Managing Director of Technology

December 2023 – January 2025
  • Reporting to CEO, responsible for all Technology in the Group, including offshore development, platform resilience, and Technology strategy.
Staysure Group

Director of Technology Strategy and AI

March 2023 – December 2023
  • Established Architecture Governance committee and took ownership of all solution design.
  • Stabilised all systems ensuring reliability and security of service.
Suncorp Group

Enterprise Architect – Digital

October 2018 – March 2023
  • Progressed from Solutions Architect to Enterprise Architect at Australia's 2nd largest insurer and 6th largest bank.
  • Architectural responsibility for all self-service assets across Suncorp insurance, including strategy development.
  • Design and strategy for developing and delivering frontend assets including the AAMI App.
Tesco Bank

Head of IT – Tesco Pay+ / PayQwiq

February 2015 – July 2018
  • Led the UK's largest retailer digital wallet, available in 3,000+ Tesco stores with 500K+ customers — transaction every 1.5 seconds.
  • Won 'Best Achievement in Retail Payments' at the Card & Payments Awards.
  • Grew the product from a small Proof-of-Concept to nationwide scale across both retail and banking.
  • Software development, code review and coaching in Java (Spring Boot), Oracle, MySQL, and Cloud technology.
Lloyds Banking Group

Tech Lead – Digital Banking Platform

October 2011 – February 2015
  • Led the redesign of the UK's largest Internet banking platform (10M+ users, 1.6 billion logins in 2015).
  • Designed and implemented the Halifax Cashback Extras / Lloyds Everyday Offers data monetisation proposition.
  • Oversight of redesigning the platform's secure site across multiple Group brands.

Expertise

Technology Leadership

Leading large-scale engineering organisations, setting technology strategy, and building high-performing cultures across global teams.

CTO Strategy Agile

Enterprise Architecture

Designing and governing enterprise-scale architectures across financial services and retail, ensuring reliability, security, and scalability.

TOGAF Solution Design Governance

Security & Compliance

MSc in Advanced Security & Digital Forensics (GCHQ endorsed). Active OWASP contributor. Embedding security and compliance throughout the development lifecycle.

OWASP Cyber Security Forensics Compliance

Cloud & Platforms

Hands-on experience with cloud technology, CI/CD pipelines, and platform resilience at scale across banking and insurance sectors.

Cloud CI/CD Resilience

Digital Products

End-to-end delivery of award-winning digital products — from mobile apps and digital wallets to internet banking platforms serving millions.

Mobile Web Payments

Software Engineering

Remains hands-on with emerging technologies and continues programming. Deep background in Java, Spring Boot, databases, and modern practices.

Java Spring Boot AI

Education & Certifications

MSc Advanced Security & Digital Forensics
Edinburgh Napier University
2014 – 2016
Endorsed by GCHQ
BSc Computer Science
London Metropolitan University
2008 – 2011

Certifications & Training

TOGAF 9.2 Foundation
Cambridge Judge Business School – CTO Programme
Cambridge Judge – Strategic Thinking for the CXO
Cambridge Judge – Digital Transformation: Strategy to Execution

Let's Connect

Interested in discussing technology leadership, architecture, or potential opportunities? I'd love to hear from you.