Head Of Engineering

Head of Engineering About RunSybil Founded in 2023 by Ari Herbert-Voss and Vlad Ionescu, RunSybil is on a mission to automate hacker intuition. We’re building Sybil: an AI-driven pentester that discovers vulnerabilities before they’re exploited. As adversaries adopt AI to increase their attack surface, we’re putting cutting-edge offensive security into the hands of defenders. Backed by strong investor support and early customer traction, our team is composed of experts from OpenAI, Meta, Mandiant, Palantir, Cruise, Trail of Bits, and Aptiv. About the Role We are looking for a Head of Engineering to build and lead the team behind our AI-powered pentesting platform. You will partner directly with our CTO to shape technical strategy, translate customer needs into product reality, and establish the engineering culture from the ground up. This is a foundational role with real ownership over how we build and what we ship. What You'll Do: Build and lead a high-performing engineering team from the ground up Partner with the CTO on day-to-day technical decisions, architecture, and engineering strategy Prioritize an environment that values velocity and iteration over lengthy planning cycles and documentation-heavy processes Own delivery of our AI-powered pentesting platform, ensuring we ship features that solve real customer problems Drive creative execution: solve problems in uncommon and more correct ways to create advantage for the product and the company Ask "What are we really trying to do?" before jumping to solutions Foster a culture where the team feels safe to share creative ideas, hunches, and intuition alongside data and analysis Set a high bar for quality and taste across everything the engineering team ships Establish and uphold exemplary standards for code quality, practices, and engineering culture We're Looking For Someone Who Has A Mix of The Following: 8+ years of software engineering experience with 5+ years leading engineering team Track record of building and scaling engineering teams in high-growth environments Strong product sense with high standards, deep understanding of customer motivation, and strong intuition for the main problem you are solving Ability to explain the "why" and the tradeoffs in a way that creates clarity for the team Creative mindset: you defer judgment, let ideas percolate, and ask "why not both?" Belief that great products come from quality of thinking, not just following the right process Deep understanding of modern development stacks (Python, Typescript, React/Next.js, Containerization, AWS) Preference for simple, proven technology choices over bleeding-edge complexity Startup DNA: resource awareness, urgency, and a company-survival mindset Ability and willingness to work in-person in NYC to collaborate closely with leadership Location: On-site role based in New York City with remote flexibility when needed. Some travel may be required. Compensation The base pay range for this role is $250,000 – $300,000 per year.