StrongestLayer is building AI-native email security architecture designed for threats that defeat pattern-matching systems. The company pivoted from security awareness training after early customers discovered its phishing detection plugin caught advanced threats that legacy gateway solutions missed. In a recent episode of Category Visionaries, we sat down with Alan LeFort, CEO of StrongestLayer, to discuss why architectural generation matters more than vendor reputation in email security, and how they’re using transparent proof-of-concept methodology to displace 20-year incumbents. Topics Discussed: - Why AI-generated attacks with n=1 datasets break signature-based detection architectures - The convergence of legitimate marketing automation and phishing techniques (lookalike domains, intent signals, AI-personalized messaging) - How 2% of attack types represent 90% of breach value, forecast to reach 17% of volume by 2027 - Transparent POC strategy achieving 85% meeting-to-POC and 100% qualified-POC-to-technical-win conversion - Stage-based ICP selection: targeting 1,000-10,000 seats for sub-6-month sales cycles with enterprise compliance requirements - Harvard Kennedy School research: AI enables 88% employee profiling from public data, 95% cost reduction for targeted campaigns, and 60% click rates versus 12% baseline GTM Lessons For B2B Founders: - Deploy transparent POCs as category displacement weapons: When attacking entrenched incumbents, StrongestLayer runs one-week POCs behind existing email security gateways with zero commercial pressure—just visibility into what’s being missed. At a sub-1,000-seat company running behind a top-three market leader, they surfaced 80 advanced threats in one week. This approach converts 85% of first meetings to POC and 100% of qualified POCs to technical wins. The insight: In technical categories where buyers are sophisticated, removing evaluation friction and letting comparative performance speak eliminates trust barriers faster than enterprise reference selling. - Stage-match your ICP to burn rate tolerance, not TAM: Alan deliberately excludes Fortune 500 despite universal email security need: ”When their procurement team is bigger than your whole company, not a good scene.” Instead, they target 1,000-10,000 seats—enterprises with SOC2/compliance obligations but without Fortune 500 security budgets or staffing. These accounts close in under 6 months. The framework: Define ICP by sales cycle length your runway can sustain, then expand segments as capital position improves. Your ICP should evolve with company stage, not remain static based on ideal long-term positioning. // 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