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System1, Inc. Chief Financial Officer Form 4 filing shows a routine share withholding tied to equity compensation. On 01/28/2026, 258 shares of Class A Common Stock were withheld at $4.18 per share to cover taxes on the vesting of 625 restricted stock units.
After this transaction, the CFO beneficially owns 119,906 shares of Class A Common Stock, which includes 53,352 unvested RSUs. This reflects standard tax settlement mechanics rather than an open‑market sale.
System1, Inc. reported an insider transaction by Chief People Officer Elizabeth Sestanovich. When 375 previously granted restricted stock units vested, the company withheld 211 shares of Class A Common Stock at $4.18 per share to cover her tax withholding obligation. After this tax-related share withholding, she beneficially owns 59,289 shares, which include 42,680 unvested RSUs.
System1, Inc. Chief Ad Operations Officer Brian Coppola reported a small share withholding tied to restricted stock units. On 01/28/2026, 231 shares of Class A common stock were withheld at $4.18 per share to cover taxes upon vesting of 469 RSUs. After this, he beneficially owned 66,229 shares, including 43,016 unvested RSUs, all held directly.
System1, Inc. officer Daniel J. Weinrot, General Counsel & Secretary, reported an automatic share withholding tied to equity compensation. On January 28, 2026, upon vesting of 375 restricted stock units (RSUs), the company withheld 211 shares of Class A common stock at $4.18 per share to cover tax obligations.
After this tax withholding, Weinrot beneficially owned 69,394 shares of Class A common stock in total, which the disclosure states includes 55,180 unvested RSUs. The filing characterizes the transaction with code F, indicating shares withheld for taxes rather than an open‑market sale.
System1, Inc. reported that director Frank Martire Jr. resigned from its Board of Directors, effective at the close of business on January 9, 2026. He had served on the board since before the company’s deSPAC merger but was not serving on any Board committee at the time of his resignation.
The company stated that Mr. Martire’s decision to step down did not result from any disagreement with System1 regarding its operations, policies, or practices, indicating this is a voluntary governance change rather than a dispute-driven departure.
System1, Inc. reported that it received a noncompliance notice from the New York Stock Exchange after failing to meet minimum market capitalization and stockholders’ equity requirements. As of December 5, 2025, the company’s 30‑trading‑day average market capitalization was below $50 million, and its last reported stockholders’ equity as of September 30, 2025 was also below $50 million, triggering a violation of NYSE Section 802.01B.
System1 has an 18‑month period to cure these deficiencies, subject to NYSE approval of a business plan showing how it will regain compliance. The company plans to notify the NYSE by December 22, 2025 of its intent to submit this plan by January 22, 2026 and is evaluating available alternatives. System1 also issued a press release on December 12, 2025 disclosing the notice of noncompliance.
System1, Inc. reported that on December 1, 2025, its largest individual shareholder, Cannae Holdings, LLC, sold 2,344,482 shares of Class A common stock in a privately negotiated off-market transaction. The buyer, Kenloch Holdings, LLC, is a new entity formed by certain members of management and independent directors and managed by co-founder, chief executive officer and board chairman Michael Blend.
Kenloch agreed to pay a total of $9,979,315.50, or $4.2565 per share, made up of $5,239,328.11 in cash and a secured promissory note for $4,739,987.39 that is collateralized by the shares purchased. In connection with this sale, director Ryan Caswell resigned from the board effective at the close of business on December 1, 2025, and his resignation was stated not to be due to any disagreement with the company’s operations, policies or practices.
System1, Inc. received an updated ownership report from investor William P. Foley, II and his entity Trasimene Trebia, LLC on its Class A common stock. The Reporting Persons now beneficially own a total of 390,473 shares, representing 4.8% of the Class A common stock, based on 8,128,321 shares outstanding as of October 29, 2025. This total includes 385,137 shares directly owned by Mr. Foley and 5,336 shares directly owned by Trasimene Trebia, LLC, which by itself represents 0.1% of the class. They state that the securities were not acquired and are not held for the purpose of changing or influencing control of System1.
Cannae Holdings has sharply reduced its stake in System1, Inc. (SST) and now holds under 5% of the company’s Class A common stock. In a privately negotiated sale on December 1, 2025, Cannae Holdings, LLC sold 2,344,482 shares of System1 Class A common stock at $4.2565 per share, for total consideration of approximately $10.0 million under a Stock Purchase Agreement dated November 24, 2025. Cannae received $5.2 million in cash at closing and a note receivable for the remaining roughly $4.8 million of proceeds.
Following this transaction, Cannae Holdings, Inc. and Cannae Holdings, LLC report beneficial ownership of 356,797 shares, representing 4.4% of System1’s Class A common stock based on 8,128,321 shares outstanding as of October 29, 2025. They state that, as of this amendment, they are not beneficial owners of more than five percent of the class and may no longer be deemed part of a group that owns more than five percent due to their withdrawal from a shareholder agreement.
System1, Inc. (SST): Cannae updates ownership on Schedule 13D/A. Cannae Holdings, Inc. and Cannae Holdings, LLC report beneficial ownership of 2,701,279 shares of Class A common stock, representing 33.2% of the Class A outstanding. The percentage is calculated based on 8,128,321 Class A shares outstanding as of October 29, 2025, as reported in the company’s Form 10‑Q filed on November 5, 2025.
The filing notes that System1’s reported increase in Class A shares outstanding changed Cannae’s ownership by more than one percent versus the prior amendment. Cannae reports 27.0% total voting power. The filing states no ownership of the 1,869,607 Class C shares outstanding as of October 29, 2025. The reporting persons disclose no transactions in Class A shares during the past 60 days.
The filing references a Shareholders Agreement under which certain parties may constitute a “group,” with members filing separate Schedules 13D; the reporting persons disclaim beneficial ownership of shares solely by reason of that agreement.