CHWY's three largest insider shareholders as of September 22, 2026 are Sumit Singh (Chief Executive Officer, 1.03Mn shares), James A Star (Director, 325.99K shares), Satish Mehta (Chief Technology Officer, 273.83K shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Sumit Singh | Chief Executive Officer | 898,291 | 127,364 | 1,025,655 | 51.8% | 03 Sep, 2026 |
| 2 | Satish Mehta | Chief Technology Officer | 273,835 | 0 | 273,835 | 13.8% | 03 Feb, 2026 |
| 3 | Stacy Bowman | Chief Accounting Officer | 245,561 | 0 | 245,561 | 12.4% | 06 Aug, 2024 |
| 4 | Mario Jesus Marte | Chief Financial Officer | 203,023 | 0 | 203,023 | 10.3% | 30 Jun, 2023 |
| 5 | William G. Billings | Chief Accounting Officer | 57,055 | 0 | 57,055 | 2.9% | 03 Sep, 2026 |
| 6 | Susan Helfrick | General Counsel | 55,759 | 0 | 55,759 | 2.8% | 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 | Martin H. Nesbitt | Director | 10,665 | 0 | 10,665 | 0.5% | 13 Jul, 2026 |
| 13 | Kristine Dickson | Director | 10,665 | 0 | 10,665 | 0.5% | 13 Jul, 2026 |
| 14 | Christopher S. Deppe | Chief Financial Officer | 9,576 | 0 | 9,576 | 0.5% | 03 Sep, 2026 |
| 15 | Da-Wai Hu | General Counsel Secretary | 4,203 | 0 | 4,203 | 0.2% | 03 Sep, 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 |
|---|---|---|---|---|---|---|---|---|
| 01 Sep, 2026 | Sumit Singh | Chief Executive Officer | Disposed F | 7,567 | $23.80 | $180.09K | 898,291 | Direct |
| 01 Sep, 2026 | Christopher S. Deppe | Chief Financial Officer | Disposed F | 1,541 | $23.80 | $36.68K | 9,576 | Direct |
| 01 Sep, 2026 | Da-Wai Hu | General Counsel Secretary | Disposed F | 445 | $23.80 | $10.59K | 4,203 | Direct |
| 01 Sep, 2026 | William G. Billings | Chief Accounting Officer | Disposed F | 625 | $23.80 | $14.88K | 57,055 | Direct |
| 01 Sep, 2026 | Sumit Singh | Chief Executive Officer | Disposed F | 1,273 | $23.80 | $30.30K | 127,364 | Indirect |
| 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 | 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 | 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 | James Larry Nelson | 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 | Deborah G Ellinger | 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 |
| 09 Jul, 2026 | Martin H. Nesbitt | 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 |
| 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 |