Chewy, Inc. (CHWY) — Insider Trading

AI-Powered SEC Filing Analysis

Latest Insider Trading Filed: 2026-05-05

Key Insights

Chief Accounting Officer William G. Billings executed a net stock acquisition of approximately 132,118 RSUs and PRSUs with staggered vesting schedules extending through August 2028, indicating significant long-term equity compensation tied to continued employment.
The filing reflects a modest tax withholding transaction (1,064 shares at $25.42) from RSU settlement, which is a routine administrative event rather than discretionary insider buying or selling activity.
Billings holds substantial unvested equity grants with the largest tranche (43,750 RSUs) vesting 58.5% in August 2026, suggesting the company is retaining key financial leadership through multi-year equity incentives aligned with shareholder interests.
The performance-based RSUs (14,470 shares) were certified as earned based on 2025 fiscal year performance conditions achieved, demonstrating achievement of company performance targets and reinforcing management confidence in business execution.

Want the newest filings?

This analysis covers the filing from 2026-05-05. New 10-K, 10-Q and 8-K filings are analyzed the moment they are released — exclusively in the app.

Download on the App Store Open in app →

Earlier Insider Trading filings

Filed: 2026-05-05

General Counsel & Secretary Hu Da-Wai executed a net share settlement on 05/01/2026, with 909 shares withheld for tax obligations related to RSU vesting, indicating routine equity compensation activity rather than discretionary insider buying.
The executive holds substantial unvested equity grants totaling approximately 222,646 RSUs and PRSUs across multiple vesting schedules through 2028, demonstrating significant long-term incentive alignment with company performance and continued employment.
Multiple performance-based restricted stock units (PRSUs) with certified achievement of 2024-2025 performance conditions suggest management confidence in meeting company targets, with vesting milestones scheduled through early 2028.

Filed: 2026-05-05

CFO Christopher Deppe received significant equity compensation totaling approximately 468,619 RSUs and PRSUs granted on April 8, 2026, indicating strong retention efforts and alignment with long-term company performance.
The compensation structure includes substantial performance-based RSUs (4,342 PRSUs) with vesting tied to 2025 fiscal year performance metrics certified in March 2026, suggesting management confidence in achieving company objectives.
Multiple tranches of RSUs vest over 2026-2029 with the largest grant (346,670 RSUs) vesting over four years (30% in Dec 2026, then 25%/25%/20% annually), demonstrating a balanced approach to executive retention and incentive alignment.
A tax withholding transaction of 2,857 shares at $25.42 on May 1, 2026 represents routine administrative processing related to RSU settlement, with no indication of discretionary selling by the CFO.

Filed: 2026-05-05

CEO Sumit Singh executed a significant sale of 83,306 shares on 05/04/2026 at $25.60 per share through a Rule 10b5-1 trading plan adopted on January 16, 2026, indicating pre-planned equity reduction rather than opportunistic trading.
Singh holds substantial beneficial ownership with approximately 2.07 million shares directly owned and additional holdings through spouse accounts, maintaining significant alignment with shareholders despite the recent sale activity.
The filing reflects active RSU and PRSU vesting schedules with multiple tranches vesting through 2027-2028, indicating long-term incentive compensation structure designed to retain the CEO through performance milestones.
Tax withholding transactions on 05/01/2026 reduced direct holdings by 15,462 shares at $25.42, demonstrating routine equity compensation settlement practices typical for executive compensation.

Filed: 2026-04-10

William G. Billings, the Chief Accounting Officer of Chewy, Inc., acquired 32,571 restricted stock units (RSUs) on April 8, 2026 as part of his compensation package.
Billings also holds additional RSUs, performance-based RSUs, and common stock in Chewy, indicating a significant stake in the company.
The vesting of these equity awards is tied to continued employment with Chewy, suggesting Billings' commitment to the company's long-term success.

Filed: 2026-04-10

The reporting person, Hu Da-Wai, is the General Counsel and Secretary of Chewy, Inc. and has received a significant number of restricted stock units (RSUs) and performance-based RSUs (PRSUs) as part of their compensation.
The RSUs and PRSUs are subject to time-based and performance-based vesting conditions, which suggests the company is aligning the reporting person's interests with those of shareholders.
The insider transactions indicate the reporting person is not actively buying or selling Chewy's stock, suggesting they are holding their equity position and focused on the long-term success of the company.

Filed: 2026-04-10

The filing person, Christopher S. Deppe, the Chief Financial Officer of Chewy, Inc., has acquired a significant number of restricted stock units (RSUs) and performance-based restricted stock units (PRSUs) totaling 458,654 shares.
The vesting of these RSUs and PRSUs is subject to time-based and performance-based conditions, indicating the company's commitment to incentivizing the executive team and aligning their interests with shareholders.
The filing person also holds additional shares of Chewy, Inc. common stock, further demonstrating his ownership and alignment with the company's long-term success.

Filed: 2026-04-10

Sumit Singh, the CEO of Chewy, Inc., has received a significant grant of 394,868 restricted stock units (RSUs) and other RSU grants to his spouse, indicating strong alignment between the CEO and shareholders.
The CEO also has a substantial number of performance-based restricted stock units (PRSUs) and time-based RSUs, suggesting a focus on long-term value creation for the company.
The insider transactions, including both direct and indirect holdings, suggest a high level of management commitment and confidence in the company's future prospects.

Filed: 2026-04-06

The reporting person, Da-Wai Hu, is the General Counsel and Secretary of Chewy, Inc., indicating they hold a key leadership role.
Da-Wai Hu has received significant equity-based compensation in the form of performance-based restricted stock units (PRSUs) and time-based restricted stock units (RSUs), aligning their interests with shareholders.
The recent transactions show Da-Wai Hu selling 8,149 shares of Chewy's Class A common stock, potentially for diversification or liquidity purposes, while still maintaining a substantial equity stake in the company.

Filed: 2026-04-06

Sumit Singh, the CEO of Chewy, Inc., has reported a transaction in which he disposed of 1,021 shares of Class A common stock to cover tax withholding obligations, suggesting he continues to hold a substantial equity stake in the company.
Chewy, Inc. has granted Sumit Singh performance-based restricted stock units (PRSUs) and time-based restricted stock units (RSUs) that are subject to vesting conditions, aligning his interests with those of shareholders.
The filing reveals that Sumit Singh and his spouse hold a significant number of Class A common shares in Chewy, Inc., indicating a high level of insider ownership and alignment with shareholder interests.

Filed: 2026-03-27

Insider Da-Wai Hu, who serves as General Counsel and Secretary, has been granted 49,962 performance-based restricted stock units (PRSUs) and 29,856 PRSUs from previous grants that have vested, indicating the company's confidence in his leadership and the alignment of his interests with shareholders.
Hu also holds significant direct ownership of 76,299 shares of Chewy's Class A common stock, as well as additional RSUs that will vest over time, suggesting a strong commitment to the company's long-term success.
The granting and vesting of these equity awards to a key executive provides visibility into Chewy's compensation practices and the company's efforts to incentivize and retain its leadership team.

Filed: 2026-03-27

The reporting person, William G. Billings, has acquired 14,470 performance-based restricted stock units (PRSUs) of Chewy, Inc. (CHWY) which will vest on March 1, 2028, subject to the satisfaction of certain performance conditions.
Billings has also been granted 43,750 and 27,026 restricted stock units (RSUs) which will vest over time, indicating his continued involvement and commitment to the company.
The insider transactions, including the acquisition of PRSUs and RSUs, suggest Billings' positive outlook on Chewy's long-term prospects and alignment with shareholder interests.

Filed: 2026-03-27

Christopher S. Deppe, the Chief Financial Officer of Chewy, Inc., acquired 4,342 performance-based restricted stock units (PRSUs) on March 25, 2026, which are eligible for vesting on March 1, 2028 subject to continued employment and achievement of certain performance conditions.
Deppe also holds various other restricted stock units (RSUs) granted between 2022 and 2025, representing a significant portion of his total beneficial ownership in Chewy's Class A common stock.
The pattern of insider equity awards and vesting suggests Chewy's management team is aligned with shareholders through long-term incentives, which could be viewed positively.

Filed: 2026-03-27

The CEO, Sumit Singh, acquired a significant amount of 526,284 performance-based restricted stock units (PRSUs) and 47,653 PRSUs for his spouse, indicating his strong commitment and confidence in the company's future performance.
The filing also shows that the CEO holds a substantial number of restricted stock units (RSUs) and PRSUs, totaling over 2 million shares, suggesting strong alignment between his interests and those of shareholders.
Insider ownership, including the CEO and his spouse, accounts for a significant portion of the company's total outstanding shares, which could signal an opportunity for long-term value creation.

Filed: 2026-03-03

Chewy CEO Sumit Singh conducted a large insider sale, disposing of 30,267 shares through a tax withholding transaction related to vested restricted stock units (RSUs). This may signal a potential change in his outlook or a desire to diversify his personal holdings.
The filing also shows that Singh holds a substantial equity stake in Chewy, with over 1.2 million shares beneficially owned, including RSUs and performance-based RSUs, indicating his continued alignment with shareholders.
Insider transactions by the CEO and his spouse suggest ongoing insider activity, which investors may want to monitor for any material changes in ownership patterns or potential indications of the company's future performance.

Filed: 2026-03-03

William G. Billings, the Chief Accounting Officer of Chewy, Inc., reported the acquisition of 43,750 restricted stock units (RSUs) on September 20, 2024, which will vest in 2026 and 2027.
Billings also reported the acquisition of 27,026 RSUs on September 20, 2024, which will vest over a three-year period starting in 2026.
Additionally, Billings reported the acquisition of 19,033 RSUs on April 8, 2025, which will vest over a three-year period starting in 2026.

Other reports for Chewy, Inc.

Current Report Annual Report

Important Information

AI-generated analysis is for informational purposes only. Always read original SEC filings and consult with qualified professionals before making investment decisions.