SELLEST OSAST
Mike McKenna, Co-Founder and CRO of Manifold Security, to dig into why the jump from LLMs to autonomous agents is the biggest inflexion point in cybersecurity and why most existing security tools aren't built for it.
Mike's path into cyber started with a stroke of luck: his then-girlfriend (now wife) fielded a cold recruiting call for Coalfire and pointed them his way. What followed was eight years watching Coalfire scale from 100 people and $30M in revenue to a compliance powerhouse, with Mike's average deal size growing from $30–40K to $300K. A formative stint at Protect AI under three-time founder Ian Swanson showed him what elite decision-making looks like at startup speed. When Protect AI sold to Palo Alto Networks, Mike and his co-founders, Neal Swaelens and Oleksandr Yaremchuk saw the next big gap: first-generation AI security was built for chatbots, not for agents that act autonomously across enterprise systems.
Key Topics Covered:
How a cold call and a quick-thinking girlfriend launched a 15-year cybersecurity career
The mentors who shaped Mike's sales philosophy from craft improvement to enterprise rigour
Why the jump from LLMs to agents is more impactful than most people realise
Hiring sales talent for a category that barely exists yet prioritising plasticity over pedigree
When to transition from founder-led sales to a dedicated team
How AI is changing outbound sales and the second-order consequences of flooded inboxes
First-gen vs. second-gen AI security: why classifying natural language isn't enough
What Manifold actually does: runtime visibility into agent behaviour on the endpoint
The AI bubble debate and why the demand curve looks different from late-90s dark fibre
Mike's advice for anyone considering a career in cybersecurity
Mike McKenna is Co-Founder and Chief Revenue Officer at Manifold Security, an AI Detection & Response platform securing autonomous AI agents on enterprise endpoints. Before founding Manifold, Mike spent eight years at Coalfire and served as part of the early go-to-market team at Protect AI (later acquired by Palo Alto Networks). Mike and his co-founders launched Manifold out of stealth in March 2026 with an $8M seed round led by Costanoa Ventures. He holds a degree from Johns Hopkins University and is based in San Diego.
Find Mike on LinkedIn: linkedin.com/in/mikemckenna9 Learn more about Manifold: manifold.security
This episode of Cyber Security Matters is brought to you by neuco.
