Chegg, Inc. (NYSE: CHGG) Chief Executive Officer Daniel Rosensweig bought 100,000 shares of the companys common stock on February 13, 2026, according to a Form 4 filed with the Securities and Exchange Commission. The purchases were executed at prices between $0.5576 and $0.5641 per share, resulting in a total reported outlay of $56,360.
After the transaction, Rosensweigs direct ownership in Chegg stands at 7,625,075 shares. In addition to those holdings, the filing notes indirect ownership of 25,000 shares by The Rosensweig Family Revocable Trust and 24,842 shares by The Rosensweig 2012 Irrevocable Childrens Trust.
These insider purchases come alongside Cheggs reported fourth-quarter 2025 financial results. The company posted an earnings per share loss of $0.01 for the quarter, which was narrower than the consensus estimate of a $0.08 loss. Revenue for the period totaled $73 million, ahead of the $71.19 million analysts had expected.
Following the quarterly report, Needham reiterated a Hold rating on Chegg shares, citing the companys strategic emphasis on growing its business-to-business operations within the Chegg Skilling division.
In corporate finance activity disclosed alongside the results, Chegg announced a privately negotiated repurchase of $20 million in aggregate principal amount of its 0% Convertible Senior Notes due 2026 for $19.4 million in cash. The company said this action is part of its broader securities repurchase program. After the repurchase, approximately $33.9 million of those Notes will remain outstanding. The company also reported it has about $122.4 million of capacity remaining under the repurchase program.
Taken together, the insider purchase, the quarters better-than-expected EPS and revenue, the reiterated analyst rating, and the targeted note repurchase outline Cheggs recent financial and strategic posture as it navigates operating results and manages its outstanding securities.
Summary
Chegg CEO Daniel Rosensweig acquired 100,000 shares on February 13, 2026, at an aggregate cost of $56,360. The company reported Q4 2025 EPS of -$0.01 on $73 million in revenue, both of which beat estimates. Chegg completed a private repurchase of $20 million of its 0% Convertible Senior Notes due 2026 for $19.4 million in cash, leaving $33.9 million of the Notes outstanding and about $122.4 million available under its repurchase program. Needham maintained a Hold rating after the results.