Matthew J. Hawkins, CEO of Waystar Holding Corp. ($WAY), sold about $23.6 million worth of shares across 14 open market transactions in the last year. His most recent sale occurred on October 15, 2025. These sales rank him 594th among 11,678 insiders by total value sold, above the average of $8.6 million per insider and 6.4 transactions. Hawkins made no open market purchases during this period.
| Transaction Date | Company | Ticker | Insider Name | Title | Transaction Type | Security | Shares | Price | Shares Owned Following | Total Shares Outstanding | % of Owned | % of Outstanding |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| March 9, 2026 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | A | Common Stock | 257096 | $0.00 | 974,570.0000 | 191,681,592 | 35.83% | 0.13% |
| Oct. 15, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 200 | $38.00 | 717,474.0000 | 0 | 0.03% | 0.00% |
| Oct. 15, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Stock Options (right to buy) | 200 | $0.00 | 1,857,680.0000 | 0 | 0.01% | 0.00% |
| Oct. 15, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Common Stock | 200 | $4.14 | 717,674.0000 | 0 | 0.03% | 0.00% |
| Sept. 23, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Common Stock | 12800 | $4.14 | 730,274.0000 | 0 | 1.78% | 0.00% |
| Sept. 22, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Common Stock | 12200 | $4.14 | 729,674.0000 | 0 | 1.70% | 0.00% |
| June 6, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | F | Common Stock | 46657 | $40.55 | 717,474.0000 | 0 | 6.11% | 0.00% |
| Sept. 23, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Stock Options (right to buy) | 12800 | $0.00 | 1,857,880.0000 | 0 | 0.68% | 0.00% |
| Sept. 22, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Stock Options (right to buy) | 12200 | $0.00 | 1,870,680.0000 | 0 | 0.65% | 0.00% |
| Sept. 23, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 12800 | $38.08 | 717,474.0000 | 0 | 1.75% | 0.00% |
| Sept. 22, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 12200 | $38.08 | 717,474.0000 | 0 | 1.67% | 0.00% |
| Aug. 12, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Stock Options (right to buy) | 46667 | $0.00 | 1,882,880.0000 | 0 | 2.42% | 0.00% |
| Aug. 12, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Common Stock | 46667 | $4.14 | 810,798.0000 | 0 | 6.11% | 0.00% |
| Aug. 12, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 46667 | $34.66 | 764,131.0000 | 0 | 5.76% | 0.00% |
| Aug. 1, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | J | Stock Options (right to buy) | 156865 | $0.00 | 1,929,547.0000 | 0 | 7.52% | 0.00% |
| Aug. 1, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | J | Stock Options (right to buy) | 156865 | $0.00 | 1,929,547.0000 | 0 | 8.85% | 0.00% |
| July 15, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 46667 | $38.26 | 764,131.0000 | 0 | 5.76% | 0.00% |
| July 15, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Common Stock | 46667 | $4.14 | 810,798.0000 | 0 | 6.11% | 0.00% |
| July 15, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Stock Options (right to buy) | 46667 | $0.00 | 1,929,547.0000 | 0 | 2.36% | 0.00% |
| June 10, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Stock Options (right to buy) | 46667 | $0.00 | 1,976,214.0000 | 0 | 2.31% | 0.00% |
| June 10, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Common Stock | 46667 | $4.14 | 810,798.0000 | 0 | 6.11% | 0.00% |
| June 10, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 2704 | $40.57 | 764,131.0000 | 0 | 0.35% | 0.00% |
| June 5, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Common Stock | 59836 | $4.14 | 823,967.0000 | 0 | 7.83% | 0.00% |
| June 5, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 59836 | $40.18 | 764,131.0000 | 0 | 7.26% | 0.00% |
| June 5, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Stock Options (right to buy) | 59836 | $0.00 | 1,272,881.0000 | 0 | 4.49% | 0.00% |
| May 27, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 140164 | $39.03 | 764,131.0000 | 0 | 15.50% | 0.00% |
| May 22, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Stock Options (right to buy) | 2153 | $0.00 | 2,420,728.0000 | 0 | 0.09% | 0.00% |
| May 23, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Stock Options (right to buy) | 197847 | $0.00 | 2,222,881.0000 | 0 | 8.17% | 0.00% |
| May 27, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Stock Options (right to buy) | 140164 | $0.00 | 2,082,717.0000 | 0 | 6.31% | 0.00% |
| May 27, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Common Stock | 140164 | $4.14 | 904,295.0000 | 0 | 18.34% | 0.00% |
| May 23, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 197847 | $38.53 | 764,131.0000 | 0 | 20.57% | 0.00% |
| May 23, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Common Stock | 197847 | $4.14 | 961,978.0000 | 0 | 25.89% | 0.00% |
| May 22, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 2153 | $39.15 | 76,413.0000 | 0 | 2.74% | 0.00% |
| May 22, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Common Stock | 2153 | $4.14 | 766,284.0000 | 0 | 0.28% | 0.00% |
| May 13, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Common Stock | 46667 | $4.14 | 810,798.0000 | 0 | 6.11% | 0.00% |
| May 13, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Stock Options (right to buy) | 46667 | $0.00 | 2,422,881.0000 | 0 | 1.89% | 0.00% |
| May 13, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 2704 | $39.46 | 764,131.0000 | 0 | 0.35% | 0.00% |
| May 13, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 43963 | $38.94 | 766,835.0000 | 0 | 5.42% | 0.00% |
| May 9, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | A | Common Stock | 264131 | $0.00 | 764,131.0000 | 0 | 52.83% | 0.00% |
| April 10, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 26546 | $36.09 | 520,121.0000 | 0 | 4.86% | 0.00% |
| April 10, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Common Stock | 46667 | $4.14 | 546,667.0000 | 0 | 9.33% | 0.00% |
| April 10, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Stock Options (right to buy) | 46667 | $0.00 | 2,469,548.0000 | 0 | 1.85% | 0.00% |
| April 10, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 20121 | $36.72 | 500,000.0000 | 0 | 3.87% | 0.00% |
| March 13, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 46155 | $35.54 | 500,500.0000 | 0 | 8.44% | 0.00% |
| March 13, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Stock Options (right to buy) | 46665 | $0.00 | 2,516,215.0000 | 0 | 1.82% | 0.00% |
| March 13, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | M | Common Stock | 46665 | $4.14 | 546,665.0000 | 0 | 9.33% | 0.00% |
| March 13, 2025 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | S | Common Stock | 500 | $36.36 | 500,000.0000 | 0 | 0.10% | 0.00% |
| June 10, 2024 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | A | Common Stock | 500000 | $0.00 | 500,000.0000 | 0 | 9999.99% | 0.00% |
| June 6, 2024 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | A | Stock Options (right to buy) | 1250000 | $0.00 | 1,250,000.0000 | 0 | 9999.99% | 0.00% |
| May 1, 2024 | Waystar Holding Corp. | $WAY | Hawkins Matthew J. | Chief Executive Officer | A | Stock Options (right to buy) | 145200 | $0.00 | 145,200.0000 | 0 | 9999.99% | 0.00% |