In this episode of The Virtual CISO Moment, Dylan Owen shares his journey from webmaster in the 1990s to leading cybersecurity teams at Raytheon and serving as CISO at Nightwing. He reflects on the challenges of transitioning into executive leadership, the realities of the vCISO role, and how SMBs can best approach detection and response. Dylan also offers insights on making security frictionless, plus how he manages stress with fitness and his love for soccer.