Kyle Winters

Lead Security Assessor
Reckon Security
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Kyle Winters

With over 30 years in the technology sector, Kyle has built a career that spans everything from coax cables to cloud compliance. Starting out repairing PCBs for computerised industrial machines, he worked his way through roles as a Novell NetWare administrator, CCNP, Microsoft SME, solution architect, and consultant, before finally discovering that his true calling was telling people their security controls don’t actually work the way they think they do.

Kyle is now a highly regarded IRAP assessor, known for his blend of deep technical expertise and laser-focused compliance insight. His experience spans Defence, Defence Industry, Commonwealth and State Governments, and the private sector, giving him a unique perspective on how organisations of all shapes and sizes try (and sometimes fail) to secure their systems.

He brings a pragmatic, no-nonsense approach to his work, balancing technical rigour with the occasional raised eyebrow. Kyle has a knack for cutting through jargon, spotting inconsistencies, and gently guiding system owners toward uncomfortable truths - always with professionalism, and sometimes with a laugh.

When he's not buried in risk registers or asking awkward questions about undocumented firewall rules, Kyle is passionate about improving the cybersecurity maturity of Australian organisations one assessment at a time.

Speaker's Sessions

15/10/25
14:00
 - 
14:40
Signals and smoke...Separating claims from capability in IRAP
Theme
Cyber Security Infrastructure
Topic
Securing Systems and Data Assets
View details
Cyber Security Infrastructure
Securing Systems and Data Assets
Breakout