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 Forward Deployed Engineer who owns the technical side of every deal. You will run demos, scope engagements, and be the person who makes sure a prospect fully understands what Sybil can do for their environment. You are equally comfortable in a discovery call with a CISO, a technical deep-dive with a red team, and a scoping conversation with a security engineer.

This role sits at the intersection of pre- and post-sales. You will stay close through onboarding and early delivery to make sure what you scoped is what we ship. At RunSybil, everyone's work is visible and every win is shared. You will have a direct hand in shaping how we bring Sybil to market and how our customers succeed.

What You Will Do:

Own the technical side of the sales cycle from first demo through close, working alongside the Account Executive on every deal
Run pre-sales scoping calls to understand a prospect's environment, attack surface, and security program maturity, then translate that into a clear picture of where Sybil fits
Work closely with Account Executives to build and deliver customer proposals, from initial scoping to presentation
Deliver compelling, customized product demonstrations that speak to the specific concerns of technical buyers
Lead engagement scoping for pilots and POCs, defining objectives, timelines, and success criteria in close collaboration with the customer
Hold your own in technical conversations with security practitioners on findings, methodology, risk and offensive security topics
Partner with Customer Success and Engineering during onboarding and early delivery to ensure customers get what was promised
Surface patterns from the field back to product, including gaps in capability, messaging, and competitive positioning
Build the SE function from scratch: demo environments, sales and scoping playbooks, technical objection handling, the works

What You Bring:

8 or more years of B2B technical sales experience in cybersecurity, security services, or a complex technical product with long evaluation cycles
Hands-on understanding of offensive security or application security with enough depth to earn credibility with practitioners
Demonstrated ability to explain technical concepts clearly to different audiences, from security engineers to C-level executives, without losing nuance
Experience running consultative discovery, scoping complex engagements, and managing technical evaluations with multiple stakeholders
Comfort working across pre-sales and post-sales without treating the handoff as someone else's problem
Strong organizational discipline to manage multiple active deals and POCs simultaneously
A builder's instinct: you figure things out rather than waiting for direction

Location:Remote (US)

Compensation: $215,000-245,000 OTE comp structure and details shared with candidates who advance. We offer meaningful equity. We want everyone here to have ownership in what we’re building.

Diverse teams build better products. RunSybil is committed to hiring people who bring different perspectives, lived experiences, and backgrounds to our work. We encourage candidates of all races, ethnicities, gender identity and expression, sexual orientation, disability or medical conditions, ages, religions, and socioeconomic backgrounds to apply. Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. If you're excited about this role but don't check every box, we still want to hear from you.

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