PiggyGPT

Private companiesCovered

Twenty Technologies

Arlington, Virginia, United States · Founded 2024

Twenty Technologies, which calls itself Twenty, builds AI-enabled offensive cyber warfare systems for the U.S. military and Intelligence Community. Its software automates the offensive cyber operations lifecycle across many targets at once, with human operators deciding what to carry out. It holds contracts with U.S. Cyber Command, and it raised a $100 million Series B at a $1 billion valuation in June 2026 and $30 million more from Khosla Ventures at $1.2 billion in July 2026.

Profile

What it builds and who buys it

  • ·Twenty builds AI-enabled, end-to-end systems for the U.S. military and Intelligence Community to conduct offensive cyber operations.Twenty (company release, PR Newswire), Jun 17, 2026
  • ·The company says its products encode operator tradecraft into the system, turning workflows that took weeks of manual effort into automated, continuous operations across hundreds of targets at once.Twenty (company site)
  • ·Its AI agents scan targets, probe networks for weak points and suggest courses of action to human operators, who choose whether to carry them out, as chief executive Joe Lin described it to Tectonic.Tectonic, Nov 24, 2025
  • ·Lin told Forbes that Twenty combines commercially available frontier models suited to a task, and those its military and intelligence customers already run, with human hacking and cyber intelligence expertise.Forbes Colombia (from Forbes US), Jul 28, 2026
  • ·Forbes reported that the Pentagon is Twenty’s only customer and that public records show only a handful of its contracts.Forbes Colombia (from Forbes US), Jul 28, 2026
  • ·Forbes reported an agreement with U.S. Cyber Command worth up to $12.6 million.Forbes Colombia (from Forbes US), Jul 28, 2026
  • ·Tectonic reported a $12.6 million Cyber Command contract in the summer of 2025 and a $240,000 Navy research contract.Tectonic, Nov 24, 2025
  • ·In June 2025 the Navy’s NAVAIR Warfare Center Aircraft Division awarded it an SBIR Phase I contract, with $138,791 obligated.USAspending.gov (award record), Jun 9, 2025
  • ·In December 2025 the Air Force contracted it for a Kill Web Management prototype to give the Air Force Office of Special Investigations an advantage against advanced persistent threat actors, with $148,586 obligated. Forbes put that contract at up to $640,000.USAspending.gov (award record), Dec 9, 2025
  • ·Lin told Tectonic in July 2026 that Twenty works across the U.S. military and Intelligence Community and that its capabilities are in operational deployment.Tectonic, Jul 22, 2026
  • ·The company declined to give Forbes full revenue figures.Forbes Colombia (from Forbes US), Jul 28, 2026
  • ·The name refers to the Double-Cross System, a British counter-espionage operation of the Second World War, Bloomberg reported.Bloomberg Law, Nov 20, 2025
  • ·Its engineering organization works from Arlington and New York City.Twenty (company site)
  • ·Lin said the 2026 capital goes to research and development, a larger D.C. headquarters and a new New York office.Tectonic, Jul 22, 2026
  • ·In May 2026 West Virginia University’s WVU Cyber program began a partnership with Twenty that gives its students internships and supports applied research in offensive cyber and AI.WVU Today (West Virginia University), May 11, 2026
  • ·Its Form D gives Delaware incorporation in 2025; the company says it was founded in 2024.SEC EDGAR (Form D), Sep 25, 2026
  • ·Its leadership page lists Joe Lin as chief executive, Leo Olson as chief technology officer, Skyler Onken as vice president of product and Pete Sorrentino as vice president of growth, all co-founders.Twenty (company site)

Founders and leadership

  • Joe LinCo-founder and chief executive

    Vice president of product management at Palo Alto Networks, which he joined through its $1.25 billion acquisition of Expanse, where he founded and led the National Security Division. A former U.S. Navy Reserve officer who has worked at the RAND Corporation.Twenty (company site)

  • Leo OlsonCo-founder and chief technology officer

    Led the engineering team that delivered Palo Alto Networks’ first cyber operations capability, after serving as technical director of Expanse’s National Security Division. Over two decades as a U.S. Army signals intelligence and cyber operations chief warrant officer, including at U.S. Cyber Command and the National Security Agency.Twenty (company site)

  • Skyler OnkenCo-founder and vice president of product

    Over a decade at U.S. Cyber Command and the U.S. Army, including the Cyber National Mission Force, and one of the military’s first Master Cyber Operators. Most recently a senior principal engineer at Palo Alto Networks.Twenty (company site)

  • Pete SorrentinoCo-founder and vice president of growth

    Led business development, product management and customer success for national security customers in Palo Alto Networks’ Cortex business, after building Expanse’s public sector business. Earlier led Palantir’s federal acquisitions strategy function and served at the Department of Homeland Security.Twenty (company site)

Prospects, after the July 2026 Khosla investment

Prepared by PiggyGPT, as of Oct 15, 2026

  • ·The Pentagon is the only customer on file, Forbes reported. The public contracts are small beside the funding: up to $12.6 million with Cyber Command, an Air Force award Forbes put at up to $640,000, and a Navy SBIR Phase I award. Classified work does not appear in public records, and the company has published no revenue.Forbes Colombia (from Forbes US), Jul 28, 2026
  • ·The company states $168 million raised and a $1.2 billion valuation in July 2026, a month after a Series B at $1 billion. A Form D filed in September records $131,314,503 of equity sold since May 2026.Twenty (company release, PR Newswire), Jul 20, 2026
  • ·Lin said the money goes to research and engineering and to expanding in Washington and New York.Tectonic, Jul 22, 2026
  • ·For the acquisition read, its investors are venture funds and In-Q-Tel, and no cited source names a strategic investor, a partner that could buy it or talks. The posture is quiet.

A summary of what the figures on this page add up to, prepared by PiggyGPT from the record on file and its cited sources. Not the Street's view, and not advice.

Funding

Last valuation

$1.2B

Post-money, Series B extensionTwenty (company release, PR Newswire), Jul 20, 2026

Last round or tender

$30Mraised

Series B extensionTwenty (company release, PR Newswire), Jul 20, 2026

A $30 million investment from Khosla Ventures, led by partner Jon Chu. The company calls it an additional investment following the Series B; Tectonic calls it a Series B extension. The company said it brought total funding to $168 million and called the $1.2 billion a valuation without saying pre- or post-money.

Latest revenue figure

—

Valuation to revenue

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Post-money valuation by round

$0$200M$400M$600M$800M$1B$1.2B$1.4BSep '26$1.2B Series B extension
DateRoundRaisedPost-money
Jul 20, 2026Series B extensionA $30 million investment from Khosla Ventures, led by partner Jon Chu. The company calls it an additional investment following the Series B; Tectonic calls it a Series B extension. The company said it brought total funding to $168 million and called the $1.2 billion a valuation without saying pre- or post-money.$30M$1.20B
Jun 17, 2026Series BLed by Accel, with Friends & Family Capital, Point72 Ventures and Caffeinated Capital. The company said the round brought total funding to $138 million and called the $1 billion a valuation without saying pre- or post-money. A Form D filed September 25, 2026 records $131,314,503 of equity sold to 12 investors from May 4, 2026, of a $131,499,718 offering; the company does not say which rounds it covers.$100M$1.00B
Nov 20, 2025Seed and Series AAnnounced together when the company emerged from stealth. The release states $38 million in total funding: a seed round led by Timothy Junio, co-founder and chief executive of Expanse, and a Series A led by Caffeinated Capital with General Catalyst and In-Q-Tel. It gives no split between the two and no valuation. The day recorded is the announcement.$38M—

Primary capital across the rounds on file: $168M

Revenue

No citable revenue figure on file.

Secondary venues

No public venue page on file.

A venue is listed when its public page named the company on the date shown. A price is the figure that page showed, under the venue’s own name for it and dated as the venue dated it; it is a level the venue publishes, not a trade. Nothing is recorded from behind a login.

Reads

Acquisition: Quiet

No cited tie to a buyer. What is on file is contracts, rounds and partnerships without one.

Prepared by PiggyGPT, as of Oct 15, 2026

Signals

  • Jun 9, 2025The Navy’s NAVAIR Warfare Center Aircraft Division signed an SBIR Phase I contract with Twenty Technologies, with $138,791 obligated.USAspending.gov (award record), Jun 9, 2025
  • Nov 20, 2025Twenty emerged from stealth with $38 million in total funding from a seed round led by Expanse’s Timothy Junio and a Series A led by Caffeinated Capital, with General Catalyst and In-Q-Tel.Twenty (company release, PR Newswire), Nov 20, 2025
  • Nov 20, 2025Bloomberg reported that Twenty signed contracts worth as much as $12.6 million in the summer of 2025, in a report on its work for U.S. military hackers.Bloomberg Law, Nov 20, 2025
  • Dec 9, 2025The Air Force signed a contract with Twenty Technologies for a Kill Web Management prototype for the Air Force Office of Special Investigations, aimed at advanced persistent threat actors, with $148,586 obligated.USAspending.gov (award record), Dec 9, 2025
  • Jun 17, 2026Twenty raised a $100 million Series B led by Accel at a $1 billion valuation.Twenty (company release, PR Newswire), Jun 17, 2026
  • Jul 20, 2026Khosla Ventures invested $30 million more at a $1.2 billion valuation.Twenty (company release, PR Newswire), Jul 20, 2026
  • Sep 25, 2026A Form D recorded $131,314,503 of equity sold to 12 investors from May 4, 2026.SEC EDGAR (Form D), Sep 25, 2026

A summary of what the figures on this page add up to, prepared by PiggyGPT from the record on file and its cited sources. Not the Street's view, and not advice.

Sources

Researched Oct 15, 2026