John T. McDonald, CEO of Upland Software, Inc. ($UPLD), made one open market sale of company shares in the last year, totaling $34,064. His most recent transaction occurred on September 11, 2025. These sales rank 10,714th out of 11,678 individual insiders, well below the average of $8.6 million per seller across 6.37 transactions on average. McDonald reported no open market purchases.
| Transaction Date | Company | Ticker | Insider Name | Title | Transaction Type | Security | Shares | Price | Shares Owned Following | Total Shares Outstanding | % of Owned | % of Outstanding |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| March 16, 2026 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 18605 | $0.54 | 2,754,625.0000 | 28,891,348 | 0.67% | 0.06% |
| Dec. 16, 2025 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 19677 | $1.49 | 2,773,230.0000 | 28,891,348 | 0.70% | 0.07% |
| Sept. 16, 2025 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 22956 | $2.48 | 2,792,907.0000 | 28,708,922 | 0.82% | 0.08% |
| Sept. 11, 2025 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | S | Common Stock | 14438 | $2.36 | 2,815,863.0000 | 28,708,922 | 0.51% | 0.05% |
| June 16, 2025 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 22957 | $1.84 | 2,830,301.0000 | 28,168,267 | 0.80% | 0.08% |
| March 16, 2025 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 24273 | $3.10 | 2,853,258.0000 | 28,168,267 | 0.84% | 0.09% |
| Jan. 28, 2025 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | A | Common Stock | 250000 | $0.00 | 2,877,531.0000 | 28,168,267 | 9.51% | 0.89% |
| Jan. 28, 2025 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | A | Performance Share Unit | 250000 | $0.00 | 250,000.0000 | 28,168,267 | 9999.99% | 0.89% |
| Dec. 16, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 17833 | $4.51 | 2,627,531.0000 | 27,440,968 | 0.67% | 0.06% |
| Dec. 9, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 49188 | $4.89 | 2,531,645.0000 | 27,440,968 | 1.91% | 0.18% |
| Dec. 10, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | M | Common Stock | 187500 | $0.00 | 2,719,145.0000 | 27,440,968 | 7.41% | 0.68% |
| Dec. 10, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 73781 | $5.31 | 2,645,364.0000 | 27,440,968 | 2.71% | 0.27% |
| Dec. 6, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | M | Performance Share Unit | 187500 | $0.00 | 312,500.0000 | 27,440,968 | 37.50% | 0.68% |
| Dec. 9, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | M | Common Stock | 125000 | $0.00 | 2,580,833.0000 | 27,440,968 | 5.09% | 0.46% |
| Dec. 10, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | M | Performance Share Unit | 187500 | $0.00 | 0.0000 | 27,440,968 | 100.00% | 0.68% |
| Dec. 6, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 73781 | $4.45 | 2,455,833.0000 | 27,440,968 | 2.92% | 0.27% |
| Dec. 6, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | M | Common Stock | 187500 | $0.00 | 2,529,614.0000 | 27,440,968 | 8.01% | 0.68% |
| Dec. 9, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | M | Performance Share Unit | 125000 | $0.00 | 187,500.0000 | 27,440,968 | 40.00% | 0.46% |
| Dec. 4, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | M | Common Stock | 31250 | $0.00 | 2,316,505.0000 | 27,440,968 | 1.37% | 0.11% |
| Dec. 3, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | M | Common Stock | 156250 | $0.00 | 2,346,739.0000 | 27,440,968 | 7.13% | 0.57% |
| Dec. 3, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 61484 | $4.37 | 2,285,255.0000 | 27,440,968 | 2.62% | 0.22% |
| Dec. 4, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 12297 | $4.00 | 2,304,208.0000 | 27,440,968 | 0.53% | 0.04% |
| Dec. 5, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | M | Common Stock | 62500 | $0.00 | 2,366,708.0000 | 27,440,968 | 2.71% | 0.23% |
| Dec. 5, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 24594 | $4.32 | 2,342,114.0000 | 27,440,968 | 1.04% | 0.09% |
| Dec. 3, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | M | Performance Share Unit | 156250 | $0.00 | 593,750.0000 | 27,440,968 | 20.83% | 0.57% |
| Dec. 4, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | M | Performance Share Unit | 31250 | $0.00 | 562,500.0000 | 27,440,968 | 5.26% | 0.11% |
| Dec. 5, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | M | Performance Share Unit | 62500 | $0.00 | 500,000.0000 | 27,440,968 | 11.11% | 0.23% |
| Sept. 16, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 17833 | $2.24 | 2,190,489.0000 | 27,265,746 | 0.81% | 0.07% |
| Aug. 9, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | P | Common Stock | 66365 | $1.96 | 2,208,322.0000 | 27,265,746 | 3.10% | 0.24% |
| Aug. 8, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | P | Common Stock | 33635 | $1.98 | 2,141,957.0000 | 27,265,746 | 1.60% | 0.12% |
| June 16, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 17834 | $2.63 | 2,108,322.0000 | 29,908,407 | 0.84% | 0.06% |
| June 5, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | A | Performance Share Unit | 500000 | $0.00 | 750,000.0000 | 29,908,407 | 200.00% | 1.67% |
| March 16, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 19330 | $4.21 | 2,126,156.0000 | 29,908,407 | 0.90% | 0.06% |
| Jan. 29, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | A | Performance Share Unit | 250000 | $0.00 | 250,000.0000 | 29,908,407 | 9999.99% | 0.84% |
| Jan. 29, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | A | Common Stock | 250000 | $0.00 | 2,145,486.0000 | 29,908,407 | 13.19% | 0.84% |
| Jan. 29, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | A | Performance Share Unit | 250000 | $0.00 | 250,000.0000 | 29,908,407 | 9999.99% | 0.84% |
| Jan. 29, 2024 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | A | Common Stock | 250000 | $0.00 | 2,145,486.0000 | 29,908,407 | 13.19% | 0.84% |
| Dec. 16, 2023 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 11650 | $4.61 | 1,895,486.0000 | 32,221,855 | 0.61% | 0.04% |
| Sept. 16, 2023 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 11650 | $3.86 | 1,907,136.0000 | 32,221,855 | 0.61% | 0.04% |
| June 16, 2023 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 11650 | $3.53 | 1,918,786.0000 | 32,221,855 | 0.60% | 0.04% |
| March 16, 2023 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | F | Common Stock | 12704 | $4.72 | 1,930,436.0000 | 32,221,855 | 0.65% | 0.04% |
| March 13, 2023 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | P | Common Stock | 10000 | $4.75 | 1,943,140.0000 | 32,221,855 | 0.52% | 0.03% |
| March 10, 2023 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | P | Common Stock | 10000 | $4.80 | 1,933,140.0000 | 32,221,855 | 0.52% | 0.03% |
| Feb. 21, 2023 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | A | Performance Share Unit | 100000 | $0.00 | 193,750.0000 | 32,221,855 | 106.67% | 0.31% |
| Feb. 21, 2023 | Upland Software, Inc. | $UPLD | MCDONALD JOHN T | CEO | A | Common Stock | 100000 | $0.00 | 1,923,140.0000 | 32,221,855 | 5.49% | 0.31% |