Eric L. Sinclair III (Ric), Chief Business Officer of Waystar Holding Corp. ($WAY), sold shares on the open market thirteen times over the last year for a total of $5.6 million. His most recent sale occurred on January 20, 2026. These insider sales rank 1788th out of 11,678 individuals by total value, compared to an average of $8.6 million across about 6.4 transactions per seller. Sinclair made no open market purchases in the period.
| Transaction Date | Company | Ticker | Insider Name | Title | Transaction Type | Security | Shares | Price | Shares Owned Following | Total Shares Outstanding | % of Owned | % of Outstanding |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Jan. 20, 2026 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Stock Options (right to buy) | 7562 | $0.00 | 173,938.0000 | 191,316,583 | 4.17% | 0.00% |
| Jan. 20, 2026 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Common Stock | 32663 | $4.14 | 515,051.0000 | 191,316,583 | 6.77% | 0.02% |
| Jan. 20, 2026 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Stock Options (right to buy) | 32663 | $0.00 | 6,141.0000 | 191,316,583 | 84.17% | 0.02% |
| Jan. 20, 2026 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | S | Common Stock | 40225 | $30.08 | 474,826.0000 | 191,316,583 | 7.81% | 0.02% |
| Jan. 20, 2026 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Common Stock | 7562 | $18.19 | 482,388.0000 | 191,316,583 | 1.59% | 0.00% |
| Dec. 22, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Common Stock | 9701 | $4.14 | 484,527.0000 | 191,316,583 | 2.04% | 0.01% |
| Dec. 22, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | S | Common Stock | 9701 | $32.82 | 474,826.0000 | 191,316,583 | 2.00% | 0.01% |
| Dec. 22, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Stock Options (right to buy) | 9701 | $0.00 | 38,804.0000 | 191,316,583 | 20.00% | 0.01% |
| Nov. 20, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Common Stock | 9701 | $4.14 | 484,527.0000 | 191,316,583 | 2.04% | 0.01% |
| Nov. 20, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Stock Options (right to buy) | 9701 | $0.00 | 48,505.0000 | 191,316,583 | 16.67% | 0.01% |
| Nov. 20, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | S | Common Stock | 9701 | $35.27 | 474,826.0000 | 191,316,583 | 2.00% | 0.01% |
| Oct. 20, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Common Stock | 9701 | $4.14 | 484,527.0000 | 0 | 2.04% | 0.00% |
| Oct. 20, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | S | Common Stock | 9701 | $36.94 | 474,826.0000 | 0 | 2.00% | 0.00% |
| Oct. 20, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Stock Options (right to buy) | 9701 | $0.00 | 58,206.0000 | 0 | 14.29% | 0.00% |
| Sept. 22, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Common Stock | 9701 | $4.14 | 484,527.0000 | 0 | 2.04% | 0.00% |
| Sept. 22, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Stock Options (right to buy) | 9701 | $0.00 | 67,907.0000 | 0 | 12.50% | 0.00% |
| Sept. 22, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | S | Common Stock | 9701 | $37.63 | 474,826.0000 | 0 | 2.00% | 0.00% |
| June 6, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | F | Common Stock | 16044 | $40.55 | 474,826.0000 | 0 | 3.27% | 0.00% |
| Sept. 8, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | S | Common Stock | 19404 | $40.03 | 474,826.0000 | 0 | 3.93% | 0.00% |
| Sept. 8, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Stock Options (right to buy) | 19404 | $0.00 | 77,608.0000 | 0 | 20.00% | 0.00% |
| Sept. 8, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Common Stock | 19404 | $4.14 | 494,230.0000 | 0 | 4.09% | 0.00% |
| Aug. 20, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Stock Options (right to buy) | 9702 | $0.00 | 97,012.0000 | 0 | 9.09% | 0.00% |
| Aug. 20, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | S | Common Stock | 9702 | $35.11 | 490,870.0000 | 0 | 1.94% | 0.00% |
| Aug. 20, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Common Stock | 9702 | $4.14 | 500,572.0000 | 0 | 1.98% | 0.00% |
| July 21, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Stock Options (right to buy) | 9702 | $0.00 | 106,714.0000 | 0 | 8.33% | 0.00% |
| July 21, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Common Stock | 9702 | $4.14 | 500,572.0000 | 0 | 1.98% | 0.00% |
| July 21, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | S | Common Stock | 9702 | $37.10 | 490,870.0000 | 0 | 1.94% | 0.00% |
| June 25, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Common Stock | 9702 | $4.14 | 500,572.0000 | 0 | 1.98% | 0.00% |
| June 25, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | S | Common Stock | 9702 | $40.22 | 490,870.0000 | 0 | 1.94% | 0.00% |
| June 25, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Stock Options (right to buy) | 9702 | $0.00 | 116,416.0000 | 0 | 7.69% | 0.00% |
| June 20, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Stock Options (right to buy) | 9702 | $0.00 | 126,118.0000 | 0 | 7.14% | 0.00% |
| June 20, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Common Stock | 9702 | $4.14 | 500,572.0000 | 0 | 1.98% | 0.00% |
| June 20, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | S | Common Stock | 9702 | $37.79 | 490,870.0000 | 0 | 1.94% | 0.00% |
| May 30, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Stock Options (right to buy) | 9702 | $0.00 | 135,820.0000 | 0 | 6.67% | 0.00% |
| May 30, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | S | Common Stock | 9702 | $40.00 | 490,870.0000 | 0 | 1.94% | 0.00% |
| May 30, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Common Stock | 9702 | $4.14 | 500,572.0000 | 0 | 1.98% | 0.00% |
| May 21, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Common Stock | 9702 | $4.14 | 500,572.0000 | 0 | 1.98% | 0.00% |
| May 21, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | S | Common Stock | 9602 | $39.16 | 490,907.0000 | 0 | 1.92% | 0.00% |
| May 21, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | S | Common Stock | 100 | $39.55 | 490,870.0000 | 0 | 0.02% | 0.00% |
| May 21, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | M | Stock Options (right to buy) | 9702 | $0.00 | 145,522.0000 | 0 | 6.25% | 0.00% |
| April 1, 2025 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | A | Common Stock | 316957 | $0.00 | 490,870.0000 | 0 | 182.25% | 0.00% |
| June 6, 2024 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | A | Stock Options (right to buy) | 434782 | $0.00 | 434,782.0000 | 0 | 9999.99% | 0.00% |
| May 1, 2024 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | A | Stock Options (right to buy) | 72600 | $0.00 | 72,600.0000 | 0 | 9999.99% | 0.00% |
| June 10, 2024 | Waystar Holding Corp. | $WAY | Sinclair III Eric L. (Ric) | Chief Business Officer | A | Common Stock | 173913 | $0.00 | 173,913.0000 | 0 | 9999.99% | 0.00% |