As of August 27, 2026, the three largest insider holders of CHWY are Sumit Singh (Chief Executive Officer, 573.94K shares), Sumit Singh (Chief Executive Officer, 454.09K shares), Christopher S. Deppe (Chief Financial Officer, 346.67K shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Sumit Singh | Chief Executive Officer | 886,630 | 125,404 | 1,012,034 | 51.9% | 04 Aug, 2026 |
| 2 | Satish Mehta | Chief Technology Officer | 273,835 | 0 | 273,835 | 14.0% | 03 Feb, 2026 |
| 3 | Stacy Bowman | Chief Accounting Officer | 245,561 | 0 | 245,561 | 12.6% | 06 Aug, 2024 |
| 4 | Mario Jesus Marte | Chief Financial Officer | 203,023 | 0 | 203,023 | 10.4% | 30 Jun, 2023 |
| 5 | William G. Billings | Chief Accounting Officer | 56,094 | 0 | 56,094 | 2.9% | 04 Aug, 2026 |
| 6 | Susan Helfrick | General Counsel | 55,759 | 0 | 55,759 | 2.9% | 16 Jun, 2023 |
| 7 | Michael Morant | General Counsel | 41,282 | 0 | 41,282 | 2.1% | 04 Aug, 2023 |
| 8 | Nathaniel Goldhaber | Director | 10,665 | 0 | 10,665 | 0.5% | 13 Jul, 2026 |
| 9 | Deborah G Ellinger | Director | 10,665 | 0 | 10,665 | 0.5% | 13 Jul, 2026 |
| 10 | James A Star | Director | 10,665 | 0 | 10,665 | 0.5% | 13 Jul, 2026 |
| 11 | James Larry Nelson | Director | 10,665 | 0 | 10,665 | 0.5% | 13 Jul, 2026 |
| 12 | Kristine Dickson | Director | 10,665 | 0 | 10,665 | 0.5% | 13 Jul, 2026 |
| 13 | Christopher S. Deppe | Chief Financial Officer | 7,206 | 0 | 7,206 | 0.4% | 04 Aug, 2026 |
| 14 | Da-Wai Hu | General Counsel Secretary | 2,823 | 0 | 2,823 | 0.1% | 04 Aug, 2026 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 31 Jul, 2026 | Sumit Singh | Chief Executive Officer | Disposed F | 28,649 | $22.82 | $653.77K | 929,874 | Direct |
| 31 Jul, 2026 | William G. Billings | Chief Accounting Officer | Disposed F | 11,134 | $22.82 | $254.08K | 56,094 | Direct |
| 31 Jul, 2026 | Christopher S. Deppe | Chief Financial Officer | Disposed F | 624 | $22.82 | $14.24K | 7,206 | Direct |
| 31 Jul, 2026 | Da-Wai Hu | General Counsel Secretary | Disposed F | 909 | $22.82 | $20.74K | 2,823 | Direct |
| 31 Jul, 2026 | Sumit Singh | Chief Executive Officer | Disposed F | 3,715 | $22.82 | $84.78K | 131,637 | Indirect |
| 03 Aug, 2026 | Sumit Singh | Chief Executive Officer | Disposed S | 43,244 | $23.01 | $995.04K | 886,630 | Direct |
| 03 Aug, 2026 | Sumit Singh | Chief Executive Officer | Disposed S | 6,233 | $23.01 | $143.42K | 125,404 | Indirect |
| 09 Jul, 2026 | Deborah G Ellinger | Director | Acquired A | 10,665 | $0.00 | $0 | 10,665 | Direct |
| 09 Jul, 2026 | Kristine Dickson | Director | Acquired A | 10,665 | $0.00 | $0 | 10,665 | Direct |
| 09 Jul, 2026 | Martin H. Nesbitt | Director | Acquired A | 10,665 | $0.00 | $0 | 10,665 | Direct |
| 09 Jul, 2026 | James A Star | Director | Acquired A | 10,665 | $0.00 | $0 | 10,665 | Direct |
| 09 Jul, 2026 | James Larry Nelson | Director | Acquired A | 10,665 | $0.00 | $0 | 10,665 | Direct |
| 09 Jul, 2026 | Nathaniel Goldhaber | Director | Acquired A | 10,665 | $0.00 | $0 | 10,665 | Direct |
| 29 Jun, 2026 | Da-Wai Hu | General Counsel Secretary | Disposed S | 100 | $19.48 | $1.95K | 4,103 | Direct |
| 29 Jun, 2026 | Da-Wai Hu | General Counsel Secretary | Disposed S | 4,103 | $19.49 | $79.97K | 0 | Direct |
| 01 Jun, 2026 | Da-Wai Hu | General Counsel Secretary | Disposed F | 445 | $22.54 | $10.03K | 4,203 | Direct |
| 01 Jun, 2026 | Sumit Singh | Chief Executive Officer | Disposed F | 1,273 | $22.54 | $28.69K | 125,915 | Indirect |
| 01 Jun, 2026 | Christopher S. Deppe | Chief Financial Officer | Disposed F | 182 | $22.54 | $4.10K | 6,247 | Direct |
| 01 Jun, 2026 | William G. Billings | Chief Accounting Officer | Disposed F | 625 | $22.54 | $14.09K | 38,937 | Direct |
| 01 Jun, 2026 | Sumit Singh | Chief Executive Officer | Disposed F | 7,567 | $22.54 | $170.56K | 885,722 | Direct |