Carolyn Woodard explores how cybersecurity insurance has evolved for nonprofits with Jenna Kirkpatrick Howard, Senior Vice President at Lockton Companies, who advises nonprofit clients on risk, insurance, and mitigation strategies to protect their boards, missions, and people.

When Carolyn and Jenna first presented a webinar together on cyber liability insurance, it was a new product that many nonprofits had never considered. Today it is nearly always required, and the risks it covers have transformed. The conversation traces that evolution, from the forgotten laptop and rogue employee scenarios of the early days to the ransomware attacks, sophisticated social engineering fraud, and emerging privacy laws driving claims now. 

Jenna also shares what insurers are doing about AI, from underwriter questions about guardrails to new endorsements affirming coverage, and why early AI-related litigation should put every nonprofit on notice about keeping a human in the loop.

Jenna and Carolyn discuss:

• How cyber claims have shifted toward ransomware and social engineering fraud, where attackers monitor an organization's email and intercept major transactions like grants, investments, or building purchases.
• What affirmative AI coverage means, and why underwriters are starting to ask how your organization uses AI and what policies protect PII and confidential data.
• Why copyright and media liability claims are rising for nonprofits, including AI-altered images and unlicensed music at events and on podcasts.
• How dependence on third-party platforms like payroll systems, cloud providers, and learning platforms creates aggregation risk, and why insurers now ask about your major vendors.
• Why increased partisan attention on nonprofits can turn employee statements, scholarship criteria, or governance issues into insurance claims.
• Where to start if you are new to an organization or unsure of your coverage: lean on your existing advisors, build a risk tracker, and align your board on top risks.

Resources Mentioned:

• Jenna Kirkpatrick Howard Linkedin
• Lockton Companies
• Cyber Risk Discussion Guide - Lockton
• AI Acceptable Use Policy Template – Community IT Innovators
• Cybersecurity Insurance for Nonprofits webinar – Community IT Innovators

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• Register to attend a webinar in real time, and find all past transcripts at https://communityit.com/webinars/
• email Carolyn at [email protected]
• on LinkedIn 
• on reddit/r/nonprofitITmanagement
• on the Community IT website

Thanks for listening.