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Stockholders’ Deficit | 6 Months Ended
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Jun. 30, 2025
Stockholders' Equity Note [Abstract] |
Stockholders’ Deficit | Stockholders’ Deficit Common stock The Company’s articles of incorporation authorizes the issuance of Class A common stock, Class B common stock, and Class C common stock. Holders of Class A common stock, Class B common stock, and Class C common stock are entitled to dividends on a pro rata basis, when, as, and if declared by the Company’s Board of Directors, subject to the rights of the holders of the Company’s preferred stock. Holders of Class A common stock are entitled to one vote per share, holders of Class B common stock are entitled to 10 votes per share, and holders of Class C common stock are entitled to zero votes per share. As of June 30, 2025, the Company had authorized 2,400.0 million shares of Class A common stock, 475.0 million shares of Class B common stock, and 800.0 million shares of Class C common stock, each at par value of $0.00001. Holders of Class B common stock voluntarily converted 0.3 million and 0.9 million shares during the three and six months ended June 30, 2025, respectively. Holders of Class B common stock voluntarily converted 0.3 million and 1.0 million shares during the three and six months ended June 30, 2024, respectively. As of June 30, 2025, 190.8 million shares of Class A common stock, 76.6 million shares of Class B common stock, and no shares of Class C common stock were issued and outstanding. As of December 31, 2024, 218.4 million shares of Class A common stock, 77.5 million shares of Class B common stock, and no shares of Class C common stock were issued and outstanding. Class A shares issued and outstanding as of June 30, 2025 and December 31, 2024 exclude unvested restricted stock awards granted to certain executives. Class A shares issued and outstanding also exclude 8.3 million unvested restricted stock awards granted to one of the Company's co-founders as of June 30, 2025 and December 31, 2024, resp ectively. See "Co-Founder Grant" section below for additional information. Preferred stock The Company's Board of Directors has the authority, without further action by the Company's stockholders, to issue up to 240.0 million shares of undesignated preferred stock with rights and preferences, including voting rights, designated from time-to-time by the Board of Directors. Stock repurchase program In February 2022, the Board of Directors authorized a $1.2 billion share repurchase program, which the Company completed during the three months ended March 31, 2024. In July 2023, the Board of Directors authorized an additional $1.2 billion share repurchase program, which the Company completed during the three months ended March 31, 2025. In December 2024, the Board of Directors authorized a third $1.2 billion share repurchase program, under which the Company continues to repurchase shares. Share repurchases are made from time-to-time in private transactions or open market purchases, as permitted by securities laws and other legal requiremen ts and are subject to a review of the circumstances in place at that time, including prevailing market prices. The program does not obligate the Company to repurchase any specific number of shares and may be discontinued at any time. During the three and six months ended June 30, 2025, the Company repurchased and subsequently retired 14.2 million and 32.2 million shares of its Class A common stock, for aggregate amounts of $403.0 million and $907.0 million, respectively. During the three and six months ended June 30, 2024, the Company repurchased and subsequently retired 11.3 million and 22.4 million shares of its Class A common stock, for aggregate amounts of $262.2 million and $543.8 million, respectively. During the three and six months ended June 30, 2025 and 2024, the 1% excise tax imposed as part of the Inflation Reduction Act is i ncluded in the cost of treasury stock acquired pursuant to common share repurchases. Additionally, repurchases during the three and six months ended June 30, 2025 included repurchase execution costs incurred in connection with the Company’s share repurchase program. Equity incentive plans Under the 2018 Plan, the Company may grant stock-based awards to purchase or directly issue shares of common stock to employees, directors, and consultants. Options are granted at a price per share equal to the fair market value of the Company's common stock at the date of grant. Options granted are exercisable over a maximum term of 10 years from the date of grant and generally vest over a period of four years. RSUs and RSAs are also granted under the 2018 Plan. The 2018 Plan will terminate 10 years after the later of (i) its adoption or (ii) the most recent stockholder-approved increase in the number of shares reserved under the 2018 Plan, unless terminated earlier by the Company's Board of Directors. The 2018 Plan was adopted on March 22, 2018. As of June 30, 2025, there were 27.8 million stock-based awards issued and outstanding and 131.8 million shares available for issuance under the Dropbox Equity Incentive Plans, Dropbox Sign's 2011 Equity Incentive Plan, DocSend's 2013 Stock Plan and DocSend's 2015 Stock Option and Grant Plan (collectively, the "Plans"). Stock option and restricted stock activity for the Plans was as follows for the six months ended June 30, 2025:
|  |  | Options outstanding |  | Restricted stock outstanding
| Number of shares available for issuance under the Plans |  | Number of shares outstanding under the Plans |  | Weighted- average exercise price per share |  | Weighted- average remaining contractual term (In years) |  | Aggregate intrinsic value |  | Number of shares outstanding under the Plans |  | Weighted- average grant date fair value per share
Balance at December 31, 2024 | 122.8 |  |  | 0.1 |  |  | $ | 6.13 |  |  | 3.9 |  | $ | 0.6 |  |  | 25.7 |  |  | $ | 23.79 |
Additional shares authorized | 14.8 |  |  | — |  |  | — |  |  | — |  |  | — |  |  | — |  |  | — |
Options exercised and restricted stock units and awards released | — |  |  | (0.1) |  |  | 6.62 |  |  | — |  |  | — |  |  | (6.2) |  |  | 24.21 |
Options and restricted stock units and awards canceled | 3.4 |  |  | — |  |  | — |  |  | — |  |  | — |  |  | (3.4) |  |  | 23.96 |
Shares withheld related to net share settlement of restricted stock units and awards | 2.5 |  |  | — |  |  | — |  |  | — |  |  | — |  |  | — |  |  | — |
Options and restricted stock units and awards granted | (11.7) |  |  | — |  |  | — |  |  | — |  |  | — |  |  | 11.7 |  |  | 27.23 |
Balance as of June 30, 2025 | 131.8 |  |  | — |  |  | $ | — |  |  | 0.0 |  | $ | — |  |  | 27.8 |  |  | $ | 25.13 |
Vested at June 30, 2025 |  |  | — |  |  | $ | — |  |  | 0.0 |  | $ | — |  |  | — |  |  | $ | — |
Unvested at June 30, 2025 |  |  | — |  |  | $ | — |  |  | 0.0 |  | $ | — |  |  | 27.8 |  |  | $ | 25.13 |
The following table summarizes information about the pre-tax intrinsic value of options exercised during the three and six months ended June 30, 2025 and 2024:
| Three Months Ended June 30, |  | Six Months Ended June 30,
| 2025 |  | 2024 |  | 2025 |  | 2024
Intrinsic value of options exercised | $ | — |  |  | $ | 0.2 |  |  | $ | — |  |  | $ | 0.4 |
As of June 30, 2025, unamortized stock-based compensation related to unvested stock options, restricted stock awards, and RSUs was $682.8 millio n. The weighted-average period over which such compensation expense will be recognized if the requisite service is provided is approximately 2.8 years as of June 30, 2025. Co-Founder Grant In December 2017, the Board of Directors approved the Co-Founder Grant, consisting of 10.3 million shares of Class A common stock in the form of RSAs granted to Drew Houston, the Company’s co-founder and Chief Executive Officer. The Co-Founder Grant is subject to service-, market-, and performance-based vesting conditions and is excluded from issued and outstanding shares until vesting. Mr. Houston holds voting rights and rights to cumulative declared dividends prior to vesting. The Co-Founder Grant vests over ten years following the Company’s IPO, based on the achievement of stock price targets during a consecutive thirty-day trading period within the Performance Period, which began on January 1, 2019. The first tranche, or 2.1 million shares, vested in the fourth quarter of 2021. Stock-based compensation expense was recognized over the derived service period using the accelerated attribution method and will not be reversed if the market conditions are not met for the remaining tranches. The Company recognized no stock-based compensation expense related to the Co-Founder Grant during the three and six months ended June 30, 2025, and $0.7 million and $1.8 million during the three and six months ended June 30, 2024. The stock-based compensation expense related to the Co-Founder Grant was fully recognized by the fourth quarter of 2024.

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- Definition The entire disclosure for shareholders' equity and share-based payment arrangement. Includes, but is not limited to, disclosure of policy and terms of share-based payment arrangement, deferred compensation arrangement, and employee stock purchase plan (ESPP). + References Reference 1: http://www.xbrl.org/2009/role/commonPracticeRef -Topic 718 -Name Accounting Standards Codification -Publisher FASB -URI https://asc.fasb.org/718/tableOfContent Reference 2: http://www.xbrl.org/2009/role/commonPracticeRef -Topic 505 -Name Accounting Standards Codification -Publisher FASB -URI https://asc.fasb.org/505/tableOfContent + Details
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