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Chris catches up with Nick Wolf, VP of Sales at Hook Security, for a wide-ranging conversation on security awareness training, the AI-driven evolution of phishing, and what MSPs need to know heading into 2027.
Nick's career has tracked the MSP channel almost from the start — from joining Datto as a teenage intern (employee #16) and rising to become the company's #1 sales rep, to roles at Skout Cybersecurity (acquired by Barracuda Networks) and Cork (cyber warranty/insurance, founded by Datto's Austin McCord), and now leading sales at Hook Security.
In this episode:
Why the user — not the software — is usually the weakest link, and what that means for how MSPs should be building their security stack
How Hook Security's live-action training content, micro-learnings, and "Campaign of the Month" autopilot model work for MSPs, including per-user pricing and a price-lock guarantee
Why classic "spot the typos" phishing training doesn't hold up anymore now that AI is writing the phishing emails too
The AI shift Nick's hearing about most from MSPs — and why he doesn't think AI replaces MSPs, but will change how clients buy from them
A shoutout to fellow Series 13 guest Jimmy Hatzel of Hatz AI
Nick's tip for MSP owners: don't be afraid to delegate and build out your team as you scale
A detour into all 50 states, national parks, Disney World, and the best food to eat in every state you visit
Connect with Nick Wolf : Website LinkedIn
Music by purple-planet.com