---
title: 'Head Of Engineering at RunSybil'
canonical: 'https://feeny.ai/job/head-of-engineering-runsybil-new-york-ghp9h2qjk15x'
type: 'job'
last_seen: '2026-09-10'
---

# Head Of Engineering at RunSybil

- **Company:** RunSybil
- **Location:** New York, NY
- **Compensation:** $250k–$300k
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-02-12
- **Last confirmed live:** 2026-09-10
- **Apply:** https://jobs.gem.com/runsybil/am9icG9zdDp0UNwOoO552-RPJVSiiWOL

## Job description

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.

## About RunSybil

## Company Overview
- **One-liner**: RunSybil is an AI-native offensive security platform that autonomously discovers and exploits real-world vulnerabilities across modern applications, acting like an elite human researcher but at machine speed.
- **Entity Type**: Private (Seed stage – $40M raised)
- **Headquarters**: San Francisco, United States (with a hub in New York City)
- **Founded**: 2023
- **Founders**: Ari Herbert-Voss (CEO) and Vlad Ionescu (CTO)

## Core Business
- **Primary industry**: Computer and Network Security (AI-powered offensive security / automated penetration testing)
- **Target customers**: Enterprise security teams (B2B) – companies needing continuous application, cloud, and infrastructure security testing
- **Mission or purpose**: “Automate hacker intuition” – give every enterprise team the equivalent of a world-class red teamer that never sleeps

## Products & Services
- **[Sybil – AI Pentesting Platform]**: An AI-driven offensive security platform that continuously tests applications and infrastructure for exploitable vulnerabilities. It maps the entire stack (code, APIs, cloud, infra), reasons like an attacker, chains vulnerabilities across layers, and validates exploitability. Delivers findings on every pull request and re-evaluates with every deployment. Covers high-risk application testing, continuous attack surface monitoring, multi-tenant/business logic testing, bug bounty/pentest replacement, and cloud/infrastructure security validation. (Type: SaaS platform)

## Market Standing
- **Valuation/Market Cap**: Not disclosed (private)
- **Key Metric**: Total Funding – $40M (Seed round, March 2026)
- **Notable Investors/Partners**: Led by Khosla Ventures (8 investors total). Team alumni include OpenAI, Meta, Mandiant, NCC Group, Trail of Bits.
- **Growth Signals**: LinkedIn followers grew +309.5% year-over-year (2,471 followers as of early 2026). Rapidly hiring across engineering, ML, and security roles. Product already delivering measurable improvements to security posture and development velocity for customers.

## Competitive Advantages
- **AI-native reasoning**: Sybil doesn’t rely on signature scanning – it dynamically interacts with systems, explores authentication boundaries, and chains vulnerabilities the way elite human attackers do, producing 90% fewer false positives.
- **Continuous, pre-validated findings**: Covers every deployment, not point-in-time pentests. Findings are validated as exploitable, eliminating triage burden.
- **Full-stack coverage**: Tests code, APIs, cloud, and infrastructure as an integrated system, finding attack paths that siloed scanners miss.
- **Founder expertise**: CEO was first security hire at OpenAI and contributed to GPT-3/Codex; CTO led offensive security at Meta and was core Llama offensive research lead. Combined AI research and elite red teaming background.

## Strategic Focus
- **Current priorities**: Scaling the platform to become the standard for continuous offensive security (CTEM Validation phase). Expanding coverage for multi-tenant and business logic testing. Building out the engineering and research team to accelerate product iteration.
- **Growth direction**: Replacing traditional bug bounty programs and periodic pentests with continuous, AI-driven testing. Enabling enterprises to move from reactive security to proactive, automated validation.

## Why Work Here
- **Culture**: Small, high-agility startup where “velocity and iteration” trump lengthy planning. Team of builders from OpenAI, Meta, Mandiant, and Trail of Bits. Emphasis on creative, hacker-like thinking – “our product automates hacker intuition.”
- **Remote/Hybrid Policy**: Hybrid with hubs in San Francisco and New York City. Remote or hybrid options available.
- **Benefits**:
  - Comprehensive insurance: Medical, dental, vision (100% employee, 80–85% dependents), travel insurance, pet insurance discounts.
  - Wellbeing: Mental health, coaching, fitness, primary care, healthcare navigation support, Employee Assistance Program.
  - Time off: Unlimited PTO (20-day suggested minimum), 14 company holidays, 12 weeks paid parental leave + flexible return.
  - Financial: 401(k) with 3% auto-enrollment, employee discounts, financial planning tools, commuter benefits.
  - Work & Culture: Company-provided laptop, regular team onsites/offsite, structured interview process that encourages LLM use.

## Sources
1. [runsybil.com/careers](https://www.runsybil.com/careers)
2. [runsybil.com/company](https://www.runsybil.com/company)
3. [runsybil.com](https://www.runsybil.com/)
4. [linkedin.com/company/runsybil](https://linkedin.com/company/runsybil)
5. [builtin.com/company/runsybil](https://builtin.com/company/runsybil)

## Other roles at RunSybil

- [Software Engineer](https://feeny.ai/job/software-engineer-runsybil-new-york-m5jwav5bx9be) — New York, NY
- [Operations Project Manager](https://feeny.ai/job/operations-project-manager-runsybil-san-francisco-14cb0vxmb025) — San Francisco, CA
- [General Interest - Join our talent community!](https://feeny.ai/job/general-interest-join-our-talent-community-runsybil-2fhjm4av5t9g)
- [Machine Learning Engineer](https://feeny.ai/job/machine-learning-engineer-runsybil-new-york-rbnhm897g717) — New York, NY
- [SRE/Infrastructure Engineer](https://feeny.ai/job/sre-infrastructure-engineer-runsybil-new-york-ka2jn7tvaqwx) — New York, NY
- [Security Research Engineer](https://feeny.ai/job/security-research-engineer-runsybil-new-york-f4rwbvexyr6h) — New York, NY