Stride Inc SEC Filings

Stride, Inc. (LRN) insider disclosure: Chief Financial Officer Donna Blackman reported a transaction on 08/12/2025 in which 2,508 shares of Stride common stock were disposed of at a price of $157.38 per share. After the transaction, Ms. Blackman beneficially owned 112,189 shares, held directly.

The filing explains the disposition represents shares withheld by the company to satisfy the executive's tax withholding obligations when restricted shares vested; the number withheld was calculated using the closing price on the vesting date (or the most recent prior market day if the vesting date fell on a weekend or holiday). The Form 4 was signed by an attorney-in-fact on 08/14/2025.

James Jeaho Rhyu, who serves as both Director and Chief Executive Officer of Stride, Inc. (LRN), reported insider transactions on 08/08/2025 and 08/09/2025. On 08/08/2025 he was granted 40,147 restricted shares (reported as acquired at $0) that vest semi-annually with 20% vesting in year one and 40% in each of the next two years. The same date also shows an award of 23,419 restricted stock rights tied to achieving specified compound annual growth rates in Stride’s share price through 09/15/2028. On 08/09/2025 the issuer withheld 3,264 shares to satisfy tax withholding related to vesting at a reported withholding price of $149.45, leaving the reporting person with 735,724 shares following the disposition. These entries reflect routine executive compensation grants and tax-withholding activity with both time- and performance-based vesting conditions.

McMullen Greerson Greene, EVP and General Counsel of Stride, Inc. (LRN), acquired equity awards on 08/08/2025 consisting of 2,676 restricted shares and 1,004 restricted stock rights. The restricted shares vest semi-annually with 20% vesting in the first year and 40% vesting in each of the next two years. The restricted stock rights are performance-based and will vest only if certain compound annual growth rates in the company’s common stock price are achieved by 09/15/2028; the amount reported represents the threshold award.

The grants were made at a $0 price and are reported as directly beneficially owned following the transactions, with 13,426 shares of common stock held directly and 1,004 restricted stock rights outstanding. These awards combine time-based and performance-based vesting conditions for executive compensation.

Todd Goldthwaite, Managing Director of Stride, Inc., reported equity awards and a small withholding transaction in early August 2025. On 08/08/2025 he received a grant of restricted common stock totaling 2,676 shares (granted at $0) that vest semi‑annually with 20% vesting in the first year and 40% vesting in each of the next two years. The filing shows beneficial ownership of 91,360 shares after the grant. On 08/09/2025 the issuer withheld 56 shares to satisfy the reporting person’s tax withholding obligation at a price of $149.45, leaving 91,304 shares beneficially owned. The filing also discloses an award of 402 restricted stock rights that vest only if specified compound annual growth rates in the company’s stock price are met by 09/15/2028 (the reported amount is the threshold award).

Donna Blackman, the Chief Financial Officer of Stride, Inc. (LRN), reported acquiring 11,375 restricted shares on 08/08/2025 that vest semi-annually: 20% in the first year and 40% in each of the next two years. After that acquisition the form reports 115,522 shares beneficially owned.

On 08/09/2025 the company withheld 825 shares to satisfy withholding taxes at a reported price of $149.45, reducing beneficial ownership to 114,697 shares. The filing also shows an award of 4,266 restricted stock rights that are contingent on specified compound annual growth rates in the company’s stock price and reference an 09/15/2028 vesting/measurement date.

Stride, Inc. (LRN) – Form 4 filing dated 08/01/2025

Managing Director Todd Goldthwaite reported equity-compensation activity that settled on 07/30/2025. A performance-based award granted 09/06/2022 vested, resulting in 6,670 common shares acquired at no cost (Code A). To cover statutory withholding taxes, 2,379 shares were immediately withheld by the issuer at $129.15 per share (Code F). After the net share settlement, the executive’s direct holdings rose to 88,684 shares, a net increase of 4,291 shares. No derivative securities were involved, and there were no open-market purchases or sales.

The transaction is routine, reflects standard equity-award vesting, and does not signal a discretionary insider buy or sell.

Stride, Inc. (LRN) – Form 4 insider activity

Chief Financial Officer Donna Blackman reported two transactions dated 07/30/2025. She acquired 41,710 shares of common stock at $0 per share following the achievement of performance objectives from a 09/06/2022 award. To satisfy withholding taxes on the vesting, the issuer concurrently withheld/disposed 17,650 shares at $129.15 per share (transaction code “F”). After both entries, Blackman’s direct beneficial ownership stands at 104,147 shares, representing a net increase of 24,060 shares.

No derivative securities were reported. The filing indicates execution under normal equity compensation terms rather than open-market purchases or sales. Insider buying—particularly by the CFO—can be interpreted as a vote of confidence, although part of the acquisition was automatically offset by tax-related share withholding.