---
title: 'Staff Product Manager - AI Evals at Twenty'
canonical: 'https://feeny.ai/job/staff-product-manager-ai-evals-twenty-arlington-1q30qk81f6dz'
type: 'job'
last_seen: '2026-11-02'
---

# Staff Product Manager - AI Evals at Twenty

- **Company:** Twenty
- **Location:** Arlington, VA
- **Compensation:** $161k–$389k
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-10-22
- **Last confirmed live:** 2026-11-02
- **Apply:** https://jobs.ashbyhq.com/twenty/77181389-843b-4130-a33e-1449a6bbd022

## Job description

## About the Company

America is under sustained cyber attack. Our adversaries infiltrate our networks, steal our IP, and degrade the digital infrastructure that modern life runs on. They’ve learned—correctly—that those attacks rarely produce consequences. Twenty was founded to change that, by making our adversaries think twice before they attack us. Our vision is American and allied primacy in cyberspace—a future where they cannot contest us, deterrence is assured, and the free world remains secure. Founded in 2024, Twenty Technologies ([www.twenty.io](http://www.twenty.io)) industrializes offensive cyber operations for the U.S. and its allies. Headquartered in Arlington, Virginia, Twenty has raised $168M from Khosla Ventures, Accel, Caffeinated Capital, Friends & Family Capital, Point72 Ventures, General Catalyst, and In-Q-Tel.

Mission | On Site | Full Time | U.S. Citizenship Required / No Active Clearance Required

## Role Summary

Twenty builds AI-enabled technology for mission-critical cyber operations. We're seeking a Staff Product Manager to help make agentic AI systems measurable, reliable, and continuously improvable. You’ll partner with AI and engineering teams to shape evaluation capabilities—from defining agent performance and product quality to turning results into useful workflows and product decisions. The strongest candidates will bring meaningful experience building or managing agentic systems, either by directly building evaluations or by building the systems that enable teams to evaluate and improve agents. Cyber experience is a plus, but not required.

## Who You Are

- You're a product-minded, technically curious operator who is excited about how agentic systems work and how to make them better.
- You bring strong product judgment and can turn complex technical needs into clear, usable product direction.
- You enjoy partnering with engineers and AI teams, asking good questions, and working through ambiguity together.
- You are rigorous about evidence and metrics, while recognizing that evaluation methods need to reflect real user and product needs.
- You take ownership, communicate clearly, and are comfortable balancing learning, execution, and iteration.

## What You’ll Do

- Own or support the product roadmap for agentic AI evaluations, translating product-area goals into clear priorities and outcomes.
- Partner closely with engineering and AI teams to understand evaluation needs, technical constraints, and user workflows.
- Define how agent performance and product quality should be assessed, including useful measures of task success, reliability, and quality.
- Turn technical evaluation needs into clear product requirements, workflows, and acceptance criteria.
- Help operationalize evaluation workflows and success metrics so teams can consistently assess agent behavior and product changes.
- Use evaluation results and feedback to identify gaps, inform product decisions, and improve the agent experience over time.

Must Have

- Strong product experience with AI or agentic systems, including experience building or managing agentic systems through product work.
- Experience directly building evaluations for agents or building the evaluation product, tooling, or system used to assess them.
- Ability to translate technical evaluation needs into product requirements, priorities, and workflows in partnership with engineering and AI teams.
- Ability to define or operationalize meaningful measures of agent performance and product quality.
- Strong communication, collaboration, and product judgment in an evolving, technically complex environment.

## Nice to Have

- Experience in cybersecurity, offensive cyber, government, defense, intelligence, or another mission-driven environment.
- Familiarity with evaluation approaches such as benchmarks, human or automated evaluation, regression testing, simulation, or analysis of agent traces.
- Experience working with products that combine autonomous systems with meaningful human judgment and oversight.

## Benefits

What's on the table:

- Health. Medical, dental, and vision plan options. Life / AD&D, disability coverage options.
- Family. Paid parental leave for eligible full-time employees. 12 weeks for birthing parents, 4 for non-birthing parents, 6 weeks for adoptive, foster, or intended parents through surrogacy.
- Vacation. Paid holidays and flexible PTO. Take what you need.
- Retirement. 401(k) with pre-tax and Roth options. HSA/FSA options, dependent care FSA.

Benefits vary by location, role, and eligibility. Full plan details provided during the interview and offer process.

If this role sounds like you, apply and share with us your interest Due to U.S. government contract and security requirements, this role is limited to U.S. citizens. Some positions may also require eligibility to obtain and maintain a U.S. Government security clearance. Any active clearance requirement will be listed in the role description. Twenty is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, veteran status, disability, or any other protected status, consistent with applicable law. If you need a reasonable accommodation during the hiring process, let us know and we will work with you.

## About Twenty

## Company Overview
- **One-liner**: Twenty builds and scales the software and capabilities of modern cyber conflict, industrializing the American arsenal for the war of now.
- **Entity Type**: Private (Series B; $138M total funding as of June 2026)
- **Headquarters**: Arlington, Virginia, United States
- **Founded**: 2024
- **Founders**: Joe Lin (CEO), Peter S., Skyler O.

## Core Business
- **Primary industry**: Cyber warfare and national security (Computer and Network Security)
- **Target customers**: U.S. military and Intelligence Community (B2G)
- **Mission**: Deliver industrial-scale cyber capabilities, ensuring the U.S. and its allies are able to deter and defeat their adversaries [twenty.io/careers](https://twenty.io/careers/).

## Products & Services
- **Cyber Warfare Platform**: Intelligent, autonomous end-to-end systems that accelerate the entire offensive cyber operations lifecycle. Encodes elite tradecraft directly into software, transforming workflows that once took weeks of manual effort into automated, continuous operations across hundreds of targets simultaneously. [twenty.io](https://twenty.io/)

## Market Standing
- **Valuation/Market Cap**: Not disclosed
- **Key Metric**: Total funding $138M (as of June 2026), including a $38M Series A led by Caffeinated Capital in November 2025 and a subsequent $100M round in June 2026 [aventure.vc](https://aventure.vc/companies/twenty-arlington-va-us) [prnewswire.com](https://www.prnewswire.com/news-releases/twenty-raises-38m-to-transform-cyber-warfare-at-industrial-scale-302622230.html)
- **Notable Investors/Partners**: Caffeinated Capital, General Catalyst, In-Q-Tel, Accel, Point72 Ventures, Friends & Family Capital [twenty.io/careers](https://twenty.io/careers/)
- **Growth Signals**: Headcount grew 245% YoY, reaching ~50 employees; 34+ active job postings as of July 2026; emerged from stealth in November 2025 with over $100M in government contracts [linkedin.com](https://www.linkedin.com/company/twentytechnologies) [prnewswire.com](https://www.prnewswire.com/news-releases/twenty-raises-38m-to-transform-cyber-warfare-at-industrial-scale-302622230.html)

## Competitive Advantages
- **Elite team**: Composed of the top 0.1% of cyber operators (from USCYBERCOM, NSA, DHS, U.S. Marine Corps, Navy, Army) and proven builders (from Palantir, Palo Alto Networks, Expanse) [twenty.io/careers](https://twenty.io/careers/)
- **Proven track record**: The founding team built the most successful SaaS cyber product in U.S. military history and defended tens of thousands of networks [twenty.io](https://twenty.io/)
- **100X improvement**: Industrial-scale automation replaces manual, bespoke methods, fundamentally reshaping how the U.S. and allies engage in cyber conflict [twenty.io](https://twenty.io/)
- **Strategic backing**: Supported by top defense-tech VCs and In-Q-Tel (the CIA’s venture arm)

## Strategic Focus
- Accelerating the delivery of intelligent, autonomous cyber warfare systems to close critical gaps in U.S. offensive capabilities
- Countering adversaries such as the People’s Republic of China (PRC) in the cyber domain
- Expanding partnerships across the U.S. military and Intelligence Community, with deployments already in active combat operations [prnewswire.com](https://www.prnewswire.com/news-releases/twenty-raises-38m-to-transform-cyber-warfare-at-industrial-scale-302622230.html)

## Why Work Here
- **Mission-driven impact**: Your code directly affects mission success or failure — “the difference between mission success and mission failure” [twenty.io/careers](https://twenty.io/careers/)
- **Elite peer group**: Work alongside top 0.1% cyber operators and world-class technologists
- **Rapid growth**: 245% headcount increase YoY; 39 open roles across engineering, product, finance, growth, and talent [twenty.io/careers](https://twenty.io/careers/)
- **Culture**: “Serious work, savage wit, zero excuses.” Emphasis on solving “crazy-hard problems” that nation-state adversaries face. “No one is coming to save us, so we’d better do it ourselves.” [twenty.io/careers](https://twenty.io/careers/)
- **Work environment**: Primarily on-site at secure locations (Arlington, VA HQ; Fort Meade, MD; San Antonio, TX; Augusta, GA). Most roles require relocation to the Washington, DC area or other government facilities. [twenty.io/careers](https://twenty.io/careers/)
- **Notable perks**: Not explicitly detailed, but the focus is on building revolutionary capabilities for national security rather than typical engagement metrics.

## Sources
1. [twenty.io](https://twenty.io/)
2. [twenty.io/careers](https://twenty.io/careers/)
3. [linkedin.com](https://www.linkedin.com/company/twentytechnologies)
4. [prnewswire.com](https://www.prnewswire.com/news-releases/twenty-raises-38m-to-transform-cyber-warfare-at-industrial-scale-302622230.html)
5. [aventure.vc](https://aventure.vc/companies/twenty-arlington-va-us)

## Other roles at Twenty

- [Senior Recruiter, G&A](https://feeny.ai/job/senior-recruiter-g-a-twenty-new-york-t6n4kg82330t) — New York, NY
- [Staff / Principal Technical Program Manager](https://feeny.ai/job/staff-principal-technical-program-manager-twenty-arlington-6s3spncwngtm) — Arlington, VA
- [Senior/Staff Product Manager, Autonomous Cyber Operations](https://feeny.ai/job/senior-staff-product-manager-autonomous-cyber-operations-twenty-arlington-dzhh1jts0stg) — Arlington, VA
- [Staff Product Manager, Data & Platform Infrastructure](https://feeny.ai/job/staff-product-manager-data-platform-infrastructure-twenty-new-york-h16vr56wzsx5) — New York, NY
- [Staff Product Manager, Data & Platform Infrastructure](https://feeny.ai/job/staff-product-manager-data-platform-infrastructure-twenty-arlington-0wfs8tz8waat) — Arlington, VA
- [Senior Recruiter, GTM & Customer Success](https://feeny.ai/job/senior-recruiter-gtm-customer-success-twenty-arlington-4qnt6gex6h36) — Arlington, VA
- [Strategic Finance and Business Operations Associate](https://feeny.ai/job/strategic-finance-and-business-operations-associate-twenty-arlington-vh3tn5y5c4n8) — Arlington, VA
- [Offensive Solutions Architect](https://feeny.ai/job/offensive-solutions-architect-twenty-arlington-44ckspb6qyt7) — Arlington, VA
- [Mission Deployment Lead](https://feeny.ai/job/mission-deployment-lead-twenty-fort-meade-0vg1dzm8eyzq) — Fort Meade, MD
- [Mission Deployment Lead](https://feeny.ai/job/mission-deployment-lead-twenty-chantilly-d2n69shq4vsv) — Chantilly, VA