As of September 05, 2026, Toast's top three insider holders are Investment Dining Group, Llc Technology (TenPercentOwner, 37.84Mn shares), Capital Management, L.P. Hmi (TenPercentOwner, 11.05Mn shares), Jonathan Grimm (Chief Technology Officer, 3.08Mn shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Investment Dining Group, Llc Technology | TenPercentOwner | 37,843,646 | 0 | 37,843,646 | 73.2% | 25 Jul, 2023 |
| 2 | Capital Management, L.P. Hmi | TenPercentOwner | 0 | 11,047,586 | 11,047,586 | 21.4% | 31 Jan, 2022 |
| 3 | Stephen Fredette | President | 931,449 | 0 | 931,449 | 1.8% | 06 Jul, 2026 |
| 4 | Crossover Management X, Ltd. Technology | TenPercentOwner, Other | 0 | 625,000 | 625,000 | 1.2% | 29 Oct, 2021 |
| 5 | Paul D Bell | Director | 232,148 | 0 | 232,148 | 0.4% | 16 Jun, 2026 |
| 6 | Brian R Elworthy | General Counsel | 196,909 | 0 | 196,909 | 0.4% | 06 Jul, 2026 |
| 7 | Christopher P Comparato | Chief Executive Officer | 187,140 | 0 | 187,140 | 0.4% | 15 May, 2025 |
| 8 | Elena Gomez | President, Cfo | 160,150 | 0 | 160,150 | 0.3% | 11 Aug, 2026 |
| 9 | Mark J Hawkins | Director | 101,860 | 0 | 101,860 | 0.2% | 16 Jun, 2026 |
| 10 | Aman Narang | Ceo | 70,451 | 0 | 70,451 | 0.1% | 06 Jul, 2026 |
| 11 | Jonathan Vassil | Chief Revenue Officer | 69,966 | 0 | 69,966 | 0.1% | 04 Sep, 2026 |
| 12 | David Yuan | Director | 36,311 | 23,373 | 59,684 | 0.1% | 10 Jun, 2025 |
| 13 | James Michael Matlock | Principal Accounting Officer | 55,548 | 0 | 55,548 | 0.1% | 05 Aug, 2024 |
| 14 | Hilarie A. Koplow | Director | 48,147 | 0 | 48,147 | 0.1% | 16 Jun, 2026 |
| 15 | Susan Chapman-Hughes | Director | 14,530 | 0 | 14,530 | 0.0% | 13 Mar, 2026 |
| 16 | Deval L Patrick | Director | 13,260 | 0 | 13,260 | 0.0% | 14 Mar, 2025 |
| 17 | Richard Kent Bennett | Director | 0 | 10,512 | 10,512 | 0.0% | 16 Jun, 2026 |
| 18 | Jonathan Grimm | Chief Technology Officer | 6,868 | 0 | 6,868 | 0.0% | 05 May, 2022 |
| 19 | Rossana Niola | Principal Accounting Officer | 4,306 | 0 | 4,306 | 0.0% | 05 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 |
|---|---|---|---|---|---|---|---|---|
| 02 Sep, 2026 | Jonathan Vassil | Chief Revenue Officer | Acquired M | 14,280 | $2.21 | $31.56K | 84,246 | Direct |
| 02 Sep, 2026 | Jonathan Vassil | Chief Revenue Officer | Disposed S | 5,100 | $33.54 | $171.06K | 79,146 | Direct |
| 02 Sep, 2026 | Jonathan Vassil | Chief Revenue Officer | Disposed S | 9,180 | $34.10 | $312.99K | 69,966 | Direct |
| 02 Sep, 2026 | Jonathan Vassil | Chief Revenue Officer | Disposed M | 14,280 | $0.00 | $0 | 285,871 | Direct |
| 21 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Acquired M | 47,673 | $17.38 | $828.56K | 117,639 | Direct |
| 21 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Acquired M | 37,607 | $17.33 | $651.73K | 155,246 | Direct |
| 21 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Disposed S | 85,280 | $36.34 | $3.10Mn | 69,966 | Direct |
| 21 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Disposed M | 47,673 | $0.00 | $0 | 190,575 | Direct |
| 21 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Disposed M | 37,607 | $0.00 | $0 | 175,256 | Direct |
| 19 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Acquired M | 7,399 | $17.38 | $128.59K | 77,365 | Direct |
| 19 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Acquired M | 6,532 | $17.33 | $113.20K | 83,897 | Direct |
| 19 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Disposed S | 13,931 | $36.01 | $501.70K | 69,966 | Direct |
| 19 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Disposed M | 7,399 | $0.00 | $0 | 238,248 | Direct |
| 19 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Disposed M | 6,532 | $0.00 | $0 | 212,863 | Direct |
| 11 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Acquired M | 7,651 | $17.38 | $132.97K | 77,617 | Direct |
| 11 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Acquired M | 6,146 | $17.33 | $106.51K | 83,763 | Direct |
| 11 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Disposed S | 13,797 | $36.01 | $496.86K | 69,966 | Direct |
| 11 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Disposed M | 7,651 | $0.00 | $0 | 245,647 | Direct |
| 11 Aug, 2026 | Jonathan Vassil | Chief Revenue Officer | Disposed M | 6,146 | $0.00 | $0 | 219,395 | Direct |
| 07 Aug, 2026 | Aman Narang | Ceo | Disposed S | 42,105 | $35.13 | $1.48Mn | 119,843 | Indirect |