The $2.3M Mistake Hiding in Your Cyber Policy

Overview

Four expert-led webinars. Real-world cyber risk, SOC strategy, AI governance, and vendor risk—plus live Q&A and take-home playbooks.

Summer 2026 Cyber Webinar Series is a four-part, 30-minute webinar series for mid-market leaders who need practical answers on the topics boards, insurers, and regulators are asking about right now: cyber insurance readiness, Managed SOC / detection, AI governance, and third-party vendor risk.

Each session is designed to be fast, tactical, and immediately usable. Less theory, more here's what to do next.

What to Expect If You Attend

• Four concise sessions (30 minutes each) with time-boxed, real-world content and live Q&A

• Working frameworks and checklists you can bring to leadership, audits, renewals, or vendor reviews

• Examples and teardowns (denied claims, detection failures, Shadow AI sprawl, vendor breach cascades) to show what good looks like in 2026

• Recordings + slides delivered after each session (attend live for Q&A and the attendee bonus offers)

Series Format

• 0:00-5:00 Welcome + why the topic matters now

• 5:00-25:00 Practical content (frameworks, examples, and playbooks)

• 25:00-30:00 Live Q&A + next steps

Who Should Attend

Built for CEOs, CIOs, CISOs, IT Directors, GRC Leads, and General Counsel. If you own risk, security operations, compliance, renewal readiness, or vendor oversight this series will help you tighten your program without adding noise.

AGENDA

Mike O'Connor, VP, Brown & Brown, Christopher Yula, VP of Sales & Strategy, CyberSecOp

In 2024, a mid-market manufacturer attested to MFA compliance on its cyber renewal — and watched a $2.3M ransomware claim get denied over one missed VPN account. This is no longer the exception. Coalition data shows 82% of denied cyber claims involved organizations without fully implemented MFA, and 41% of applications are now rejected on first submission. Carriers have moved from questionnaire-based to evidence-based underwriting, and the gap between what executives think they bought and what their policy will actually pay is the largest it has ever been.

Join CyberSecOp and Brown & Brown for a focused 30-minute session where we break down real denied claims, expose the hidden gaps in 2026 policies covering AI, social engineering, and nation-state exclusions, and give you the seven evidence checkpoints your carrier will require at renewal. You will leave knowing exactly whether your policy will pay when it matters most.

Why Mid-Market Companies Stopped Building Their Own SOC

Overview

Four expert-led webinars. Real-world cyber risk, SOC strategy, AI governance, and vendor risk—plus live Q&A and take-home playbooks.

Summer 2026 Cyber Webinar Series is a four-part, 30-minute webinar series for mid-market leaders who need practical answers on the topics boards, insurers, and regulators are asking about right now: cyber insurance readiness, Managed SOC / detection, AI governance, and third-party vendor risk.

Each session is designed to be fast, tactical, and immediately usable. Less theory, more here's what to do next.

What to Expect If You Attend

• Four concise sessions (30 minutes each) with time-boxed, real-world content and live Q&A

• Working frameworks and checklists you can bring to leadership, audits, renewals, or vendor reviews

• Examples and teardowns (denied claims, detection failures, Shadow AI sprawl, vendor breach cascades) to show what good looks like in 2026

• Recordings + slides delivered after each session (attend live for Q&A and the attendee bonus offers)

Series Format

• 0:00-5:00 Welcome + why the topic matters now

• 5:00-25:00 Practical content (frameworks, examples, and playbooks)

• 25:00-30:00 Live Q&A + next steps

Who Should Attend

Built for CEOs, CIOs, CISOs, IT Directors, GRC Leads, and General Counsel. If you own risk, security operations, compliance, renewal readiness, or vendor oversight this series will help you tighten your program without adding noise.

AGENDA

Jack Stose, SOC Manager, CyberSecOp, Christopher Yula, VP of Sales & Strategy , CyberSecOp

In 2025, the average organization took 181 days to identify a breach and another 60 to contain it. Meanwhile, attackers broke out of their initial foothold in 62 minutes — and Mandiant's 2026 M-Trends report documented intrusion team hand-offs happening in 22 seconds. Defenders are operating on calendar time. Attackers are on a stopwatch. For mid-market organizations, the in-house SOC math has stopped working: a true 24x7 rotation requires 8 to 12 analysts, costs $1.5M to $3M annually before tooling, and 65% of SOC analysts are considering leaving within the year. Join CyberSecOp's SOC Manager for a 30-minute look inside what a properly run Managed SOC actually does, how SIEM, UEBA, XDR, and EDR work together, and the Build/Buy/Partner framework mid-market CIOs are using to cut detection time from 241 days to under 14.

49% of Your Team Is Using AI You Don’t Know About...

Overview

Four expert-led webinars. Real-world cyber risk, SOC strategy, AI governance, and vendor risk—plus live Q&A and take-home playbooks.

Summer 2026 Cyber Webinar Series is a four-part, 30-minute webinar series for mid-market leaders who need practical answers on the topics boards, insurers, and regulators are asking about right now: cyber insurance readiness, Managed SOC / detection, AI governance, and third-party vendor risk.

Each session is designed to be fast, tactical, and immediately usable. Less theory, more here's what to do next.

What to Expect If You Attend

• Four concise sessions (30 minutes each) with time-boxed, real-world content and live Q&A

• Working frameworks and checklists you can bring to leadership, audits, renewals, or vendor reviews

• Examples and teardowns (denied claims, detection failures, Shadow AI sprawl, vendor breach cascades) to show what good looks like in 2026

• Recordings + slides delivered after each session (attend live for Q&A and the attendee bonus offers)

Series Format

• 0:00-5:00 Welcome + why the topic matters now

• 5:00-25:00 Practical content (frameworks, examples, and playbooks)

• 25:00-30:00 Live Q&A + next steps

Who Should Attend

Built for CEOs, CIOs, CISOs, IT Directors, GRC Leads, and General Counsel. If you own risk, security operations, compliance, renewal readiness, or vendor oversight this series will help you tighten your program without adding noise.

AGENDA

Tom Guadagno, CISO, CyberSecOp , Christopher Yula, VP of Sales & Strategy , CyberSecOp

In January 2026, BlackFog surveyed 2,000 employees and found that 49% admit to using AI tools their employer never approved, while the average enterprise logs 223 AI-related data policy violations every month. IBM's 2025 breach report puts a price on it: $670,000 added to the average breach when Shadow AI is involved, with 20% of organizations reporting breaches directly caused by ungoverned AI. The regulatory window has closed. Texas TRAIGA is in effect, the Colorado AI Act and EU AI Act both begin enforcement in 2026, and the SEC is actively pursuing AI disclosure cases. Most organizations still cannot answer the first question their board, regulator, or insurer will ask: what AI is actually running here right now?

Join CyberSecOp's AI Governance practice for a 30-minute working session covering the 10-domain assessment framework aligned to NIST AI RMF and ISO 42001, Shadow AI inventory tactics, and a 30/60/90-day remediation roadmap you can take to your board next quarter.

Their Breach. Your Brand. Why 30% of Breaches Now Start with...

Overview

Four expert-led webinars. Real-world cyber risk, SOC strategy, AI governance, and vendor risk—plus live Q&A and take-home playbooks.

Summer 2026 Cyber Webinar Series is a four-part, 30-minute webinar series for mid-market leaders who need practical answers on the topics boards, insurers, and regulators are asking about right now: cyber insurance readiness, Managed SOC / detection, AI governance, and third-party vendor risk.

Each session is designed to be fast, tactical, and immediately usable. Less theory, more here's what to do next.

What to Expect If You Attend

• Four concise sessions (30 minutes each) with time-boxed, real-world content and live Q&A

• Working frameworks and checklists you can bring to leadership, audits, renewals, or vendor reviews

• Examples and teardowns (denied claims, detection failures, Shadow AI sprawl, vendor breach cascades) to show what good looks like in 2026

• Recordings + slides delivered after each session (attend live for Q&A and the attendee bonus offers)

Series Format

• 0:00-5:00 Welcome + why the topic matters now

• 5:00-25:00 Practical content (frameworks, examples, and playbooks)

• 25:00-30:00 Live Q&A + next steps

Who Should Attend

Built for CEOs, CIOs, CISOs, IT Directors, GRC Leads, and General Counsel. If you own risk, security operations, compliance, renewal readiness, or vendor oversight this series will help you tighten your program without adding noise.

AGENDA

Paul Nowak, CISO, CyberSecOp, Christopher Yula, VP of Sales & Strategy , CyberSecOp

In 2024, third-party involvement in breaches doubled year-over-year to 30% of all incidents, and SecurityScorecard independently tracked the number at 35.5%. The MOVEit vulnerability cascaded to more than 2,600 organizations. Change Healthcare exposed 70 million patient records at an estimated cost of $2.87 billion. 99% of Global 2000 companies are now connected to at least one vendor that has already been breached. The math has changed: half of mid-market organizations work with 100 or more vendors, each bringing roughly 14 indirect fourth- and fifth-party relationships behind it, and supply chain breaches take 267 days to identify and contain — the longest of any attack vector.

Join CyberSecOp's GRC and Vendor Risk practice for a 30-minute working session covering the five-stage VRM lifecycle from due diligence to offboarding, a vendor risk tiering rubric, live walkthroughs of Apptega and Risk Cognizance, and the contract clauses your legal team should never sign without reviewing.