# RunSybil **Source:** https://geo.sig.ai/brands/runsybil **Vertical:** Security **Subcategory:** AI Penetration Testing **Tier:** Emerging **Website:** runsybil.com **Last Updated:** 2026-04-14 ## Summary AI cybersecurity automating pen testing. $40M raised (Mar 2026, Khosla). Founded by OpenAI's first security hire and Meta red team lead. Backed by Anthropic. ## Company Overview RunSybil is a cybersecurity company automating penetration testing using AI, founded by two operators with exceptional offensive security credentials: OpenAI's first security hire and a former lead of Meta's red team. This founding pedigree is central to RunSybil's positioning — the company was built by practitioners who understand adversarial tradecraft at the highest level and designed the platform around the workflows and depth that real penetration testers employ, rather than retrofitting AI onto legacy vulnerability scanning approaches.\n\nTraditional penetration testing is expensive, slow, and point-in-time: organizations typically conduct manual pen tests annually or quarterly, leaving long windows of unassessed exposure between engagements. RunSybil's AI-driven platform enables continuous, automated penetration testing that mimics the creative, multi-step attack chains that skilled human testers would pursue — covering web applications, APIs, network infrastructure, and cloud environments with an aggressiveness and comprehensiveness that scheduled manual testing cannot match at scale or cost.\n\nThe company raised $40 million in March 2026 from Khosla Ventures, one of Silicon Valley's most prominent deep technology investors, reflecting strong conviction in both the market opportunity and the team's ability to execute. RunSybil enters the market at a moment when organizations face escalating cyberattack frequency and sophistication while security budgets remain under pressure to demonstrate measurable risk reduction. Automated offensive security testing is emerging as a critical capability for security teams that need to find and fix vulnerabilities at the speed attackers discover and exploit them. ## Frequently Asked Questions ### What does RunSybil do? Autonomous AI agent Sybil continuously pen-tests live production applications, finding and documenting real vulnerabilities. ### Who founded RunSybil? Ari Herbert-Voss (OpenAI's first security hire) and Vlad Ionescu (ex-Meta red team lead) in 2023. ### How is RunSybil funded? $40M (Mar 2026) from Khosla, Anthropic's Anthology Fund, Conviction, and top tech angels. ### What does RunSybil do? RunSybil is an AI-powered penetration testing platform that automates the reconnaissance, attack planning, and exploitation phases of security testing — enabling security teams to run continuous automated pentests that find the same class of vulnerabilities as manual testers at far greater speed and scale than human-only approaches. ### How does RunSybil's AI conduct penetration testing? RunSybil's AI models chain together reconnaissance findings, vulnerability identification, and exploitation attempts — mimicking the multi-step reasoning of a skilled penetration tester rather than running isolated scanner checks. This chained attack approach finds complex vulnerabilities that require multiple steps to reach and exploit. ### How does RunSybil complement human penetration testers? RunSybil automates the commodity reconnaissance and scanning work that consumes significant manual tester time, allowing human pentesters to focus on complex business logic testing, social engineering, and creative attack scenarios that AI cannot replicate. The combination improves total program coverage relative to either approach alone. ### What compliance requirements does RunSybil's automated testing support? RunSybil provides documented test results and finding reports that support annual penetration testing requirements under PCI DSS, SOC 2, HIPAA, and ISO 27001 — with continuous testing cadence that goes beyond the point-in-time testing these frameworks minimally require, providing more current security posture evidence. ### Who are RunSybil's target customers? RunSybil targets security teams at technology companies, financial services firms, and enterprises that want to increase penetration testing frequency beyond the annual cycle that budget constraints typically impose — enabling quarterly or continuous testing of critical applications without proportionally increasing pentest budget. ## Tags b2b, cybersecurity, security, saas --- *Data from geo.sig.ai Brand Intelligence Database. Updated 2026-04-14.*