Caldwell Nick V., Chief Product Officer at Peloton Interactive ($PTON), sold about $5.8 million worth of shares in thirteen open market transactions over the last 365 days, with the most recent on February 17, 2026. These sales rank 1728th among 11,678 individual insiders, below the average sale amount of $8.6 million and 6.4 transactions. He made no open market purchases in that period.
| Transaction Date | Company | Ticker | Insider Name | Title | Transaction Type | Security | Shares | Price | Shares Owned Following | Total Shares Outstanding | % of Owned | % of Outstanding |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| April 1, 2026 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | A | Restricted Stock Unit (RSU) | 916231 | $0.00 | 916,231.0000 | 421,310,905 | 9999.99% | 0.22% |
| March 15, 2026 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Restricted Stock Unit (RSU) | 115741 | $0.00 | 694,444.0000 | 421,310,905 | 14.29% | 0.03% |
| March 16, 2026 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 42632 | $3.86 | 880,956.0000 | 421,310,905 | 4.62% | 0.01% |
| March 15, 2026 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Class A Common Stock | 115741 | $0.00 | 923,588.0000 | 421,310,905 | 14.33% | 0.03% |
| Feb. 17, 2026 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 50570 | $4.15 | 807,847.0000 | 421,310,905 | 5.89% | 0.01% |
| Feb. 15, 2026 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Restricted Stock Unit (RSU) | 119332 | $0.00 | 238,663.0000 | 421,310,905 | 33.33% | 0.03% |
| Feb. 15, 2026 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Class A Common Stock | 119332 | $0.00 | 858,417.0000 | 421,310,905 | 16.15% | 0.03% |
| Jan. 9, 2026 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 75762 | $7.00 | 764,220.0000 | 421,310,905 | 9.02% | 0.02% |
| Jan. 13, 2026 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 25135 | $7.00 | 739,085.0000 | 421,310,905 | 3.29% | 0.01% |
| Dec. 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Class A Common Stock | 115741 | $0.00 | 904,599.0000 | 430,004,926 | 14.67% | 0.03% |
| Dec. 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Restricted Stock Unit (RSU) | 115741 | $0.00 | 810,185.0000 | 430,004,926 | 12.50% | 0.03% |
| Dec. 16, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 64617 | $6.21 | 839,982.0000 | 430,004,926 | 7.14% | 0.02% |
| Nov. 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Restricted Stock Unit (RSU) | 119332 | $0.00 | 357,995.0000 | 430,004,926 | 25.00% | 0.03% |
| Nov. 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Class A Common Stock | 119332 | $0.00 | 857,120.0000 | 430,004,926 | 16.17% | 0.03% |
| Nov. 17, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 68262 | $7.25 | 788,858.0000 | 430,004,926 | 7.96% | 0.02% |
| Sept. 16, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 206901 | $7.78 | 737,788.0000 | 390,037,997 | 21.90% | 0.05% |
| Sept. 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Class A Common Stock | 115741 | $0.00 | 706,025.0000 | 390,037,997 | 19.61% | 0.03% |
| Sept. 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | A | Class A Common Stock | 238664 | $0.00 | 944,689.0000 | 390,037,997 | 33.80% | 0.06% |
| Sept. 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Restricted Stock Unit (RSU) | 115741 | $0.00 | 925,926.0000 | 390,037,997 | 11.11% | 0.03% |
| Sept. 14, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | A | Restricted Stock Unit (RSU) | 459318 | $0.00 | 459,318.0000 | 390,037,997 | 9999.99% | 0.12% |
| Aug. 22, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 10477 | $8.00 | 590,284.0000 | 390,037,997 | 1.74% | 0.00% |
| Aug. 18, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 66949 | $8.42 | 600,761.0000 | 390,037,997 | 10.03% | 0.02% |
| Aug. 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Class A Common Stock | 119332 | $0.00 | 667,710.0000 | 390,037,997 | 21.76% | 0.03% |
| Aug. 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Restricted Stock Unit (RSU) | 119332 | $0.00 | 477,327.0000 | 390,037,997 | 20.00% | 0.03% |
| Aug. 7, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 30290 | $8.00 | 548,378.0000 | 390,037,997 | 5.23% | 0.01% |
| June 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Class A Common Stock | 115740 | $0.00 | 642,593.0000 | 385,591,039 | 21.97% | 0.03% |
| June 16, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 63925 | $6.99 | 578,668.0000 | 385,591,039 | 9.95% | 0.02% |
| June 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Restricted Stock Unit (RSU) | 115740 | $0.00 | 1,041,667.0000 | 385,591,039 | 10.00% | 0.03% |
| June 4, 2025 | HUBSPOT INC | $HUBS | Caldwell Nick V. | Not found | A | Common Stock | 400 | $0.00 | 2,115.0000 | 51,819,000 | 23.32% | 0.00% |
| May 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | J | Class A Common Stock | 0 | $0.00 | 526,853.0000 | 385,591,039 | 0.00% | 0.00% |
| May 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 31337 | $6.49 | 495,516.0000 | 385,591,039 | 5.95% | 0.01% |
| May 16, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 66712 | $6.28 | 526,853.0000 | 385,591,039 | 11.24% | 0.02% |
| May 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Class A Common Stock | 119331 | $0.00 | 593,565.0000 | 385,591,039 | 25.16% | 0.03% |
| May 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Restricted Stock Unit (RSU) | 119331 | $0.00 | 596,659.0000 | 385,591,039 | 16.67% | 0.03% |
| March 17, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | S | Class A Common Stock | 68727 | $6.59 | 474,234.0000 | 385,591,039 | 12.66% | 0.02% |
| March 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Restricted Stock Unit (RSU) | 115741 | $0.00 | 1,157,407.0000 | 385,591,039 | 9.09% | 0.03% |
| March 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Class A Common Stock | 115741 | $0.00 | 542,961.0000 | 385,591,039 | 27.09% | 0.03% |
| Feb. 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Class A Common Stock | 119332 | $0.00 | 478,168.0000 | 385,591,039 | 33.26% | 0.03% |
| Feb. 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Restricted Stock Unit (RSU) | 119332 | $0.00 | 715,990.0000 | 385,591,039 | 14.29% | 0.03% |
| Feb. 15, 2025 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | F | Class A Common Stock | 50948 | $9.77 | 427,220.0000 | 385,591,039 | 10.65% | 0.01% |
| Dec. 15, 2024 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Restricted Stock Unit (RSU) | 115741 | $0.00 | 1,273,148.0000 | 378,776,423 | 8.33% | 0.03% |
| Dec. 15, 2024 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Class A Common Stock | 115741 | $0.00 | 422,841.0000 | 378,776,423 | 37.69% | 0.03% |
| Dec. 16, 2024 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | F | Class A Common Stock | 64005 | $9.58 | 358,836.0000 | 378,776,423 | 15.14% | 0.02% |
| Nov. 15, 2024 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Restricted Stock Unit (RSU) | 119332 | $0.00 | 835,322.0000 | 378,776,423 | 12.50% | 0.03% |
| Nov. 15, 2024 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | F | Class A Common Stock | 240541 | $7.75 | 253,759.0000 | 378,776,423 | 48.66% | 0.06% |
| Nov. 15, 2024 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | F | Class A Common Stock | 65991 | $7.75 | 307,100.0000 | 378,776,423 | 17.69% | 0.02% |
| Nov. 15, 2024 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Class A Common Stock | 119332 | $0.00 | 373,091.0000 | 378,776,423 | 47.03% | 0.03% |
| Nov. 1, 2024 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Restricted Stock Unit (RSU) | 462963 | $0.00 | 1,388,889.0000 | 378,776,423 | 25.00% | 0.12% |
| Nov. 1, 2024 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | M | Class A Common Stock | 462963 | $0.00 | 494,300.0000 | 378,776,423 | 1477.37% | 0.12% |
| Sept. 30, 2024 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | A | Restricted Stock Unit (RSU) | 954654 | $0.00 | 954,654.0000 | 365,546,334 | 9999.99% | 0.26% |
| Aug. 23, 2024 | PELOTON INTERACTIVE, INC. | $PTON | Caldwell Nick V. | Chief Product Officer | P | Class A Common Stock | 31337 | $4.25 | 31,337.0000 | 365,546,334 | 9999.99% | 0.01% |
| June 3, 2021 | HUBSPOT INC | $HUBS | Caldwell Nick V. | Not found | A | Stock Option (right to buy) | 242 | $0.00 | 242.0000 | 0 | 9999.99% | 0.00% |
| June 5, 2023 | HUBSPOT INC | $HUBS | Caldwell Nick V. | Not found | A | Stock Option (right to buy) | 204 | $0.00 | 204.0000 | 48,065,000 | 9999.99% | 0.00% |
| June 11, 2024 | HUBSPOT INC | $HUBS | Caldwell Nick V. | Director | A | Common Stock | 412 | $0.00 | 1,715.0000 | 49,877,000 | 31.62% | 0.00% |