Dave Phillips, Chief Information Security Officer at OSHEAN, the nonprofit consortium serving more than 160 hospitals, schools, libraries, and government agencies across Rhode Island and Southeastern Massachusetts, joins Paul Knittle to explain how to build a cybersecurity program when you can't do everything at once.

He covers why frameworks like NIST CSF 2.0 should be run as a program rather than a checkbox, how an honest self-assessment surfaces the gaps that matter, and why reporting progress against a framework tells a board more than a list of security tools. Dave also shares how he approached the job as OSHEAN's first CISO by treating the organization like one of his own customers and ranking every finding by probability and business impact, and why he sees AI helping attackers find weaknesses faster than defenders can fix them.

The conversation closes with a preview of OMC26, OSHEAN's member conference on November 12 and 13, 2026.

Key Events

00:00 Welcome & Guest Intro

01:00 Lessons from Armored Fiber

03:00 Frameworks Are Not Checkboxes

07:00 Start Small, Be Honest About Gaps

09:00 Security Is a Leadership Issue

11:00 Chipping Away at the Stone

13:00 Deciding What to Defend First

16:00 AI on Attack and Defense

18:00 When Generative AI Is Just Noise

22:00 What to Expect at OMC26

• Tip worth stealing: Run an honest self-assessment against a framework, rank each gap by how likely it is to be exploited and how hard it would hit the business, then fix the highest-risk items first. Dave calls it chipping away at the stone, and says three to five years of it gets you to a mature security program.

• Worth a look: OMC26, the OSHEAN Member Conference, November 12 and 13, 2026 — Dave previews the security track on frameworks, GRC, and asset management. https://oshean.org/events/omc26/

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