Regan Timothy, CFO of Dropbox Inc. ($DBX), sold about $1.8 million in company shares across 22 open market transactions over the past year, with the latest on December 15, 2025. These sales rank 3,658th among 11,678 insiders in our database, below the average of $8.6 million per seller and 6.4 transactions. Timothy made no open market purchases in this period.
| Transaction Date | Company | Ticker | Insider Name | Title | Transaction Type | Security | Shares | Price | Shares Owned Following | Total Shares Outstanding | % of Owned | % of Outstanding |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Dec. 15, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 1500 | $28.35 | 437,647.0000 | 255,500,000 | 0.34% | 0.00% |
| Nov. 28, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 1500 | $29.64 | 439,147.0000 | 255,500,000 | 0.34% | 0.00% |
| Nov. 14, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 1500 | $30.25 | 467,121.0000 | 255,500,000 | 0.32% | 0.00% |
| Nov. 17, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | F | Class A Common Stock | 26474 | $30.36 | 440,647.0000 | 255,500,000 | 5.67% | 0.01% |
| Oct. 30, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 1500 | $28.40 | 468,621.0000 | 255,500,000 | 0.32% | 0.00% |
| Oct. 15, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 1500 | $28.62 | 470,121.0000 | 255,500,000 | 0.32% | 0.00% |
| Sept. 30, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 1500 | $30.71 | 476,621.0000 | 267,399,999 | 0.31% | 0.00% |
| Oct. 1, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 5000 | $29.76 | 471,621.0000 | 255,500,000 | 1.05% | 0.00% |
| Sept. 15, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 1500 | $30.87 | 478,121.0000 | 267,399,999 | 0.31% | 0.00% |
| Aug. 29, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $29.01 | 479,621.0000 | 267,399,999 | 0.52% | 0.00% |
| Aug. 15, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | F | Class A Common Stock | 26473 | $27.73 | 484,621.0000 | 267,399,999 | 5.18% | 0.01% |
| Aug. 15, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $27.95 | 482,121.0000 | 267,399,999 | 0.52% | 0.00% |
| July 29, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $27.98 | 511,094.0000 | 267,399,999 | 0.49% | 0.00% |
| July 15, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $26.83 | 513,594.0000 | 267,399,999 | 0.48% | 0.00% |
| June 30, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $28.40 | 526,094.0000 | 295,900,000 | 0.47% | 0.00% |
| July 1, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 10000 | $27.94 | 516,094.0000 | 267,399,999 | 1.90% | 0.00% |
| June 13, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $28.10 | 528,594.0000 | 295,900,000 | 0.47% | 0.00% |
| May 30, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $28.78 | 531,094.0000 | 295,900,000 | 0.47% | 0.00% |
| May 15, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | F | Class A Common Stock | 26474 | $29.61 | 536,094.0000 | 295,900,000 | 4.71% | 0.01% |
| May 15, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $29.53 | 533,594.0000 | 295,900,000 | 0.47% | 0.00% |
| April 30, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $28.29 | 562,568.0000 | 295,900,000 | 0.44% | 0.00% |
| April 15, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $26.94 | 565,068.0000 | 295,900,000 | 0.44% | 0.00% |
| April 1, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 10000 | $27.00 | 567,568.0000 | 295,900,000 | 1.73% | 0.00% |
| April 1, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | A | Class A Common Stock | 209777 | $0.00 | 577,568.0000 | 295,900,000 | 57.04% | 0.07% |
| March 28, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $26.57 | 367,791.0000 | 295,900,000 | 0.68% | 0.00% |
| March 14, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $25.27 | 370,291.0000 | 295,900,000 | 0.67% | 0.00% |
| Feb. 28, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $25.88 | 372,791.0000 | 295,900,000 | 0.67% | 0.00% |
| Feb. 18, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | F | Class A Common Stock | 20973 | $32.78 | 375,291.0000 | 295,900,000 | 5.29% | 0.01% |
| Feb. 7, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $32.19 | 396,264.0000 | 295,900,000 | 0.63% | 0.00% |
| Jan. 30, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $32.17 | 398,764.0000 | 295,900,000 | 0.62% | 0.00% |
| Jan. 15, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $30.37 | 401,264.0000 | 295,900,000 | 0.62% | 0.00% |
| Jan. 2, 2025 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 10000 | $29.65 | 403,764.0000 | 295,900,000 | 2.42% | 0.00% |
| Dec. 30, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $30.38 | 413,764.0000 | 306,300,000 | 0.60% | 0.00% |
| Dec. 13, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $29.99 | 416,264.0000 | 306,300,000 | 0.60% | 0.00% |
| Dec. 11, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 15000 | $30.01 | 418,764.0000 | 306,300,000 | 3.46% | 0.00% |
| Nov. 29, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $27.87 | 433,764.0000 | 306,300,000 | 0.57% | 0.00% |
| Nov. 15, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | F | Class A Common Stock | 25483 | $27.67 | 438,764.0000 | 306,300,000 | 5.49% | 0.01% |
| Nov. 15, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $27.17 | 436,264.0000 | 306,300,000 | 0.57% | 0.00% |
| Oct. 29, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $25.71 | 464,247.0000 | 306,300,000 | 0.54% | 0.00% |
| Oct. 15, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $26.18 | 466,747.0000 | 306,300,000 | 0.53% | 0.00% |
| Oct. 1, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 10000 | $25.13 | 469,247.0000 | 306,300,000 | 2.09% | 0.00% |
| Sept. 30, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $25.44 | 479,247.0000 | 318,700,000 | 0.52% | 0.00% |
| Sept. 19, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3177 | $25.00 | 481,747.0000 | 318,700,000 | 0.66% | 0.00% |
| Sept. 17, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 400 | $25.00 | 484,924.0000 | 318,700,000 | 0.08% | 0.00% |
| Sept. 13, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 2500 | $24.35 | 485,724.0000 | 318,700,000 | 0.51% | 0.00% |
| Sept. 16, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 400 | $25.00 | 485,324.0000 | 318,700,000 | 0.08% | 0.00% |
| Sept. 3, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 6023 | $25.01 | 488,224.0000 | 318,700,000 | 1.22% | 0.00% |
| Aug. 30, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $25.15 | 494,247.0000 | 318,700,000 | 0.60% | 0.00% |
| Aug. 15, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | F | Class A Common Stock | 31875 | $22.46 | 500,247.0000 | 318,700,000 | 5.99% | 0.01% |
| Aug. 15, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $22.79 | 497,247.0000 | 318,700,000 | 0.60% | 0.00% |
| July 30, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $24.38 | 532,122.0000 | 318,700,000 | 0.56% | 0.00% |
| July 15, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $22.76 | 535,122.0000 | 318,700,000 | 0.56% | 0.00% |
| July 1, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 13000 | $22.33 | 538,122.0000 | 318,700,000 | 2.36% | 0.00% |
| June 17, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $20.93 | 551,122.0000 | 336,700,000 | 0.54% | 0.00% |
| May 29, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $23.12 | 554,122.0000 | 336,700,000 | 0.54% | 0.00% |
| May 16, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $23.71 | 557,122.0000 | 336,700,000 | 0.54% | 0.00% |
| May 15, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | F | Class A Common Stock | 31873 | $24.02 | 560,122.0000 | 336,700,000 | 5.38% | 0.01% |
| April 30, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $23.60 | 591,995.0000 | 336,700,000 | 0.50% | 0.00% |
| April 15, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $23.11 | 594,995.0000 | 336,700,000 | 0.50% | 0.00% |
| April 1, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | A | Class A Common Stock | 207180 | $0.00 | 607,900.0000 | 336,700,000 | 51.70% | 0.06% |
| April 1, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 9905 | $24.33 | 597,995.0000 | 336,700,000 | 1.63% | 0.00% |
| March 27, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $24.36 | 400,720.0000 | 336,700,000 | 0.74% | 0.00% |
| March 15, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $24.02 | 403,720.0000 | 336,700,000 | 0.74% | 0.00% |
| Feb. 29, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $23.84 | 406,720.0000 | 336,700,000 | 0.73% | 0.00% |
| Feb. 23, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $23.49 | 409,720.0000 | 336,700,000 | 0.73% | 0.00% |
| Feb. 15, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | F | Class A Common Stock | 22041 | $32.41 | 412,720.0000 | 336,700,000 | 5.07% | 0.01% |
| Jan. 30, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $32.50 | 434,761.0000 | 336,700,000 | 0.69% | 0.00% |
| Jan. 16, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $31.29 | 437,761.0000 | 336,700,000 | 0.68% | 0.00% |
| Jan. 2, 2024 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 10000 | $28.85 | 440,761.0000 | 336,700,000 | 2.22% | 0.00% |
| Dec. 29, 2023 | DROPBOX, INC. | $DBX | Regan Timothy | Chief Financial Officer | S | Class A Common Stock | 3000 | $29.54 | 450,761.0000 | 349,400,000 | 0.66% | 0.00% |