In this episode of Audience 1st Podcast, Dani Woolf sits down with Jason Loomis, Chief Information Security Officer at Freshworks, to uncover the raw truth behind how CISOs evaluate security vendors, what actually moves a deal forward, and why most POVs fall flat before they even start.

Jason gets brutally honest about the emotional dynamics of enterprise buying, the real reason vendors lose trust, and what it actually takes to turn a POV into a purchase.

If you’re in product marketing, sales, or demand generation at a cybersecurity company, this episode will change how you think about the buyer journey and give you a blueprint to win trust, increase conversions, and build long-term influence with technical buyers.

What You’ll Learn in This Episode:

• Why emotional certainty - not ROI - is the key to winning a CISO’s trust

• The most common POV mistakes vendors make (and how to avoid them)

• How Jason evaluates vendors - and what gets them instantly disqualified

• The danger of relying on generic “What problems are you solving?” questions

• Why transparency beats feature-stuffing in every sales motion

• How to make your booth presence less awkward and more effective

• The impact of new SEC regulations on security budgeting and priorities

• Why buyers referring your product - even after saying no - is the ultimate win

If you’re serious about understanding what really drives buyer decisions in cybersecurity subscribe to Audience 1st Podcast. New episodes every week. Raw, unfiltered, and straight from the source - your buyers.

🎧 Listen now, take notes, and share with your GTM team.