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Stop Pentesting like it’s 2006:
6 Modern Lessons from the GigaOm Radar

In 2006, manual security snapshots and static PDF reports were the gold standard. In 2026, they are a liability. While your development teams are shipping code hourly, your security program shouldn't be waiting weeks for point-in-time results that are outdated before they’re even read.

Watch our deep dive into the findings of the v4 GigaOm Radar. Chris Ray, the Field CTO at GigaOm and lead analyst behind the report, joins Cobalt’s Anne Nielsen and Toast’s David Kosorok to break down the criteria that define the leaders in the PTaaS space. We explore why enterprises are ditching the old pentesting playbook in favor of platform-driven, integrated security testing that scales.

What you’ll learn:

  • The Time-to-Remediation Trap: Why most modern pentests are actually 20 years behind.
  • The GigaOm Blueprint: How to evaluate PTaaS vendors using specific business & technical criteria.
  • Risk over Compliance: The shift from checkbox compliance to measurable, platform-driven risk reduction.
  • 6 Tactical Lessons: Immediate changes you can apply to your offensive security program today.
SPEAKERS
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Chris Ray
Field CTO, GigaOm
Chris Ray, a seasoned professional in the cybersecurity field, brings a wealth of experience from small teams to large financial institutions, as well as industries such as healthcare, financials, and tech. He has acquired an extensive amount of experience advising and consulting with security vendors, helping them find product-market fit as well as deliver cyber security services.
DavidKosorok
David Kosorok
Director, Information Security Programs, Toast
David Kosorok leads the Information Security Program at Toast, Inc., overseeing Product Security and Security Operations. With over 25 years of experience in software and security testing – 16+ years specifically in security – he has built and scaled product security programs at organizations such as Hyland Software, DocuSign, Align Technologies, SAP Concur, and The Church of Jesus Christ of Latter-day Saints. David has earned multiple security certifications, including CISSP, CSSLP, GWAPT, CHFI, and CEH, and earned a Master of Science in Information Security and Assurance. 
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Anne Nielsen
Sr. Director, Product Marketing, Cobalt
Anne Nielsen is head of Product Marketing at Cobalt. She has 15+ years of cybersecurity experience across product management and marketing roles most recently as Head of Product at JupiterOne. Before then, Anne spent 9 years at Veracode and held positions at other startups including Rapid7 and 451 Research.