Twenty

Twenty

Autonomous offensive cyber operations platform

Overview

Twenty builds and deploys intelligent, autonomous systems for offensive cyber operations used by the U.S. military and Intelligence Community. Its software automates the offensive cyber lifecycle across hundreds of targets, turning multi-week workflows into continuous operations. The company emphasizes enterprise-grade, scalable cyber power to move beyond defensive postures and support active cyber conflicts, supported by government contracts and investors. Its goal is to provide faster, more reliable automated tools that give operators an information edge for national security missions.

Funded Recently
Significant Headcount Growth

About Twenty

Simplify's Rating
Why Twenty is rated
C+
Rated B on Competitive Edge
Rated B on Growth Potential
Rated D+ on Differentiation

Industries

Government & Public Sector

Cybersecurity

AI & Machine Learning

Defense

Company Size

11-50

Company Stage

Series B

Total Funding

$138M

Headquarters

Arlington, Virginia

Founded

2024

Your Connections

People at Twenty who can refer or advise you

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Simplify's Take

What believers are saying

  • U.S. military demand favors faster offensive cyber automation.
  • A $12.6 million Cyber Command contract validates early procurement traction.
  • In-Q-Tel participation strengthens credibility with intelligence and defense buyers.

What critics are saying

  • Policy backlash can halt procurement of offensive AI cyber tools.
  • Adversary adaptation will erode automated attack effectiveness over time.
  • Revenue concentration around early federal contracts creates fragile execution risk.

What makes Twenty unique

  • Twenty builds end-to-end offensive cyber systems for U.S. agencies.
  • It automates workflows from weeks to continuous multi-target operations.
  • Its founders include veterans from U.S. Cyber Command and Palo Alto Networks.

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Funding

Total Funding

$138M

Above

Industry Average

Funded Over

2 Rounds

Notable Investors:
Series B funding is typically for startups that have proven their business model and need more funding to expand rapidly—often by entering new markets or adding more products. Investors are usually venture capital firms that specialize in later-stage investments.
Series B Funding Comparison
Above Average

Industry standards

$35M
$45M
Linktree
$65M
Substack
$100M
ClickUp
$100M
Twenty

Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

Parental Leave

Unlimited Paid Time Off

Paid Holidays

401(k) Retirement Plan

Health Savings Account/Flexible Spending Account

Commuter Benefits

Growth & Insights and Company News

Headcount

6 month growth

-7%

1 year growth

4%

2 year growth

4%
Accel
Jun 18th, 2026
Our Investment in Twenty: Industrial-Scale Cyber Operations

Twenty is the modern, end-to-end offensive cybersecurity platform for US agencies.

PR Newswire
Nov 20th, 2025
Twenty Raises $38M to Transform Cyber Warfare at Industrial Scale

/PRNewswire/ -- Twenty, the company leading the industrial-scale transformation of cyber warfare technologies, today announced that it has raised $38 million...

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