Nightfall AI is pioneering AI-native data loss prevention (DLP) for enterprises navigating cloud, SaaS, and AI application proliferation. Founded in 2017 by former Uber engineers who witnessed data breaches firsthand, Nightfall addresses the architectural limitations and false positive problems plaguing legacy DLP solutions. By leveraging machine learning and large language models across three distinct layers—content classification, risk assessment, and forensic investigation—Nightfall delivers 10x accuracy improvements while enabling secure AI adoption. In this episode of Category Visionaries, I sat down with Rohan Sathe, Co-Founder & CEO of Nightfall AI, to explore their strategy for displacing entrenched incumbents and positioning as the security enabler for organizational AI deployment. Topics Discussed: - Nightfall’s founding thesis addressing DLP coverage gaps created by cloud and SaaS migration - Three-layer AI architecture: content classification, behavioral risk analysis, and agent-assisted forensics - Positioning against legacy DLP’s rules-based approaches and exact data match workarounds - Market education shift post-ChatGPT: from ”don’t use AI” to ”enable AI securely” - Purple brand differentiation strategy in security’s dark-themed visual landscape - Conference ROI reallocation: executive suite meetings versus booth presence at RSA and Black Hat - Mid-market to enterprise expansion pattern through peer-to-peer word-of-mouth - Founder-led LinkedIn strategy balancing market education with competitive displacement narratives - Sales team composition: domain practitioners versus traditional sales profiles GTM Lessons For B2B Founders: - Structure POVs to prove quantifiable superiority on one dimension: Rohan revealed Nightfall benchmarks against Google and Microsoft DLP APIs, demonstrating 10x accuracy improvements during proof-of-value cycles. When challenging mature categories, identify the single metric where you demonstrably outperform and architect evaluations to surface that gap. The key isn’t claiming superiority—it’s creating controlled comparisons where buyers verify it themselves. - Deploy AI across three workflow layers, not as a monolithic feature: Nightfall applies AI distinctly at content classification (identifying sensitive data with high precision), behavioral analysis (distinguishing risky data movement from standard workflows), and investigation assistance (helping analysts focus forensic efforts). This creates compounding value and defensibility. Map where AI can reduce friction at multiple decision points in your customer’s workflow rather than treating it as a single capability. - Replace field marketing spend with curated CISO access: Nightfall redirected budget from RSA and Black Hat booths to private suites hosting scheduled executive meetings. Rohan emphasized engaging ”chief information security officers who sign the checks” in intimate settings rather than booth traffic. For enterprise sales, calculate cost-per-meeting with economic buyers and reallocate spend accordingly. //  Sponsors:  Front Lines — We help B2B tech companies launch, manage, and grow podcasts that drive demand, awareness, and thought leadership. www.FrontLines.io The Global Talent Co. — We help tech startups find, vet, hire, pay, and retain amazing marketing talent that costs 50-70% less than the US & Europe. www.GlobalTalent.co // Don’t Miss: New Podcast Series — How I Hire Senior GTM leaders share the tactical hiring frameworks they use to build winning revenue teams. Hosted by Andy Mowat, who scaled 4 unicorns from $10M to $100M+ ARR and launched Whispered to help executives find their next role. Subscribe here: https://open.spotify.com/show/53yCHlPfLSMFimtv0riPyM