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Cyber-ready and risk-smart: Executive strategies that work

Jeff Olejnik
Oct 16, 2025

 

Cyberthreats are evolving faster than ever. At the same time, regulations and operational pressures are shifting nonstop. That means risk management has become far more complex — and more essential.

In this webinar, fellow leaders share how they're building resilient organizations that can withstand digital disruption while maintaining operational agility. From cyber preparedness strategies to emerging risk frameworks, discover the approaches that are keeping mid-market companies secure and competitive.

Some key highlights from their discussion include:

  • Human error is a major vulnerability: Training for both employees and customers is essential, especially in banking and healthcare.
  • AI is rapidly changing the threat landscape: Panelists expressed concern about the speed of AI adoption and its potential to introduce new risks, including insider threats and data leakage.
  • Insurance is becoming more prescriptive: Cyber insurance policies are forcing organizations to improve their security posture.
  • Regulatory compliance is necessary but often lags behind threats: Organizations must proactively use threat intelligence and risk-based approaches.
  • Rapid technology change is challenging traditional security models: Legacy approaches may not be sufficient for new AI-driven environments.
  • Peer learning and collaboration are vital: Sharing best practices and experiences helps organizations stay ahead of threats.

Explore real-world strategies from middle market executives and learn how proactive risk management can help your organization stay competitive, secure and ready for what's next.

Author(s)

Jeff Olejnik
Partner, Wipfli Advisory LLC
`Michael Simon Bodner
Michael Simon Bodner
Ph.D, President & Chief Information Officer, AWC Technology, LLC
Meghan Peck
Meghan Peck
Director, Health Center Controlled Network (HCCN), Community Health Center Association of Connecticut
Laurie Panella
Laurie Panella
Chief Information Officer, Marquette University
Amy Jay
Amy Jay
Risk Administration Officer, Adams Bank

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