Every Form 4 that Oscar Health, Inc. (OSCR) has filed with the SEC in the last 12 months is listed below, newest first, and each one links through to the document itself with the summary and the scores our analysis gives it.
A Form 4 covers the transactions officers, directors and large holders report, so if you follow OSCR and want that one kind of document rather than the whole filing history, this is the page to keep. The company's other filings, of every form, are on the full OSCR filings page.
Oscar Health, Inc. director David Plouffe acquired 641 deferred stock units on October 8, 2026, in lieu of cash retainer payments for board service. The $33.10 per-unit figure was the Class A common stock closing price used to calculate the award, not cash paid. His reported balance after the award was 8,176 deferred stock units. Each unit represents a right to one Class A share. The units are 100% vested on the grant date and may be settled in cash or shares at the issuer’s discretion.
Oscar Health, Inc. director Sid Sankaran received an award of 1,472 deferred stock units on October 8, 2026, in lieu of cash retainer payments for board service. The reported $33.10 price was the Class A common stock closing price used to calculate the award; each unit represents a right to receive one Class A share. His reported resulting position was 3,533 deferred stock units. The units are 100% vested on the grant date and, at Oscar Health’s discretion, will be settled in cash or Class A shares within 45 days after the first of service termination, a change in control, death or disability.
Oscar Health, Inc. director William Gassen received 698 deferred stock units on October 8, 2026, in lieu of cash retainer payments for board service. The units were calculated using the Class A common stock closing price of $33.10 that day; each unit represents a right to one Class A share. The grant was 100% vested on the grant date, and Gassen held 7,769 deferred stock units directly afterward. Oscar Health may settle the units in cash or Class A shares, at its discretion, within 45 days after termination of service, a change in control, death, or disability.
Oscar Health, Inc. (OSCR) director Vanessa Ames Wittman reported selling 25,000 shares of Class A Common Stock on September 18, 2026 at $32.24 per share in a sale described as an open market or private transaction. The sale was made pursuant to a Rule 10b5-1 trading plan adopted on June 18, 2026. After this transaction, she reports 112,121 shares held directly, a figure that includes shares to be issued upon vesting of one or more restricted stock units.
Oscar Health, Inc. (OSCR) reported that on September 18, 2026, entities affiliated with director, Co-Founder and Vice Chairman, and ten percent owner Joshua Kushner reallocated Oscar’s dual-class shares among various Thrive Capital funds. Thrive Capital Partners II, III and Claremount TW exchanged specified amounts of Class B Common Stock for equal amounts of Class A Common Stock held by Thrive Capital Partners VII Growth and Claremount VII, and certain funds then made pro rata, no-consideration distributions of Class A shares to their limited partners and general partners under Rule 16a-9(a) and Rule 16a-13. Class B Common Stock is convertible into Class A Common Stock on a one-to-one basis and will mandatorily convert after a set period and upon certain events, and Kushner, as sole managing member of the Thrive general partners, disclaims beneficial ownership except to the extent of his pecuniary interest.
Oscar Health, Inc. (OSCR) reported that multiple Thrive Capital funds restructured their holdings on September 18, 2026 using "J" code transactions, exchanging large blocks of Class A and Class B Common Stock among affiliated funds at a stated price of $0.00 per share. The moves included exchanges between Thrive Capital Partners II, III and Claremount TW and Thrive Capital Partners VII Growth and Claremount VII, plus pro rata distributions of Class A shares to limited partners and general partners without consideration, relying on Exchange Act Rules 16a-9(a) and 16a-13. All positions are held indirectly through the Thrive Capital funds, and Joshua Kushner, as managing member of the general partners, has voting and investment power but disclaims beneficial ownership except for his pecuniary interests.
Oscar Health, Inc. (OSCR) reported that Janet Liang, President, Oscar Insurance, sold 10,360 shares of Class A Common Stock on September 3, 2026 at a weighted average price of $31.45 per share. The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy tax withholding obligations upon vesting of equity awards. Following this transaction, she holds 248,697 shares directly, including shares to be issued upon vesting of restricted stock units.
Oscar Health, Inc. (OSCR) Chief Accounting Officer Victoria Baltrus reported selling 958 shares of Class A Common Stock on September 3, 2026 at a weighted average price of $31.45 per share. The sale was made under a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy tax withholding on vesting equity awards, and she now holds 213,631 shares, including shares to be issued from restricted stock unit vesting.
Oscar Health, Inc. (OSCR) reported that Chief Financial Officer Richard Scott Blackley sold 28,869 shares of Class A Common Stock on September 3, 2026 at a weighted average price of $31.45 per share, in transactions executed between $30.97 and $31.96, pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy his tax withholding obligations on vesting equity awards. After this sale, he directly holds 1,046,108 shares, which include shares to be issued upon vesting of restricted stock units, and indirectly holds 56,250 shares through the MQB Irrevocable Trust.
Oscar Health, Inc. (OSCR) reported that Chief Legal Officer Adam McAnaney sold 9,092 shares of Class A common stock on September 3, 2026 in an open-market transaction at a weighted average price of $31.45 per share. The sale was effected under a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy his tax withholding obligation upon the vesting of previously granted equity awards. Following this transaction, he directly holds 209,004 shares, which includes shares to be issued upon vesting of one or more restricted stock units.
Oscar Health, Inc. (OSCR) director Mario Schlosser reported selling 31,422 shares of Class A Common Stock on September 3, 2026 in an open-market transaction at a weighted average price of $31.45 per share, with individual trades ranging from $30.97 to $31.96.
The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy Schlosser’s tax withholding obligation upon vesting of previously granted equity awards. Following this transaction, he reported beneficial ownership of 449,444 shares, which includes shares to be issued upon vesting of restricted stock units.
Oscar Health, Inc. (OSCR) director Mario Schlosser reported an option exercise-and-sale sequence involving Class A and Class B common stock on August 27–28, 2026. He exercised fully vested stock options with a $9.75 exercise price, covering in total 750,000 shares of Class B common stock, which were then converted into Class A common stock on a one-to-one basis.
Across the two days, Schlosser reported open-market sales of 750,000 shares of Class A common stock, including 600,000 shares at a weighted average price of $30.34 (range $29.98–$30.73) and 150,000 shares at a weighted average price of $30.79 (range $30.59–$30.89). The exercised stock options expire on December 16, 2029. Separate from these transactions, trusts associated with Schlosser hold Class B common stock convertible into an aggregate of 1,104,999 shares of Class A common stock, and he disclaims beneficial ownership of those trust-held shares except to the extent of any pecuniary interest.
Oscar Health, Inc. (OSCR) reported an insider transaction by Chief Financial Officer Richard Scott Blackley. On 2026-08-18, an entity associated with him, the MQB Irrevocable Trust, sold 18,750 shares of Class A Common Stock at a weighted average price of $31.74 per share. Following this sale, the trust held 56,250 shares indirectly, while Blackley also held 1,074,977 shares directly, which include shares to be issued upon vesting of one or more restricted stock units.
Gassen William reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health, Inc. director William Gassen received a grant of 684 deferred stock units on July 9, 2026, as a compensation award in lieu of cash board retainer fees. Each unit represents a right to receive one share of Class A common stock and was valued at $31.20, the closing stock price on the grant date. The units are 100% vested at grant and will be settled in cash or shares, at the company’s discretion, within 45 days after specified events such as termination of service or a change in control. Following this grant, Gassen holds 7,071 deferred stock units directly.
Sankaran Sid reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health, Inc. director Sid Sankaran received a grant of 858 deferred stock units on July 9, 2026, as board compensation elected in lieu of cash retainers. Each unit represents a right to receive one share of Class A common stock, valued at $31.20 per unit based on the closing share price on that date. The units are 100% vested on the grant date and will be settled in cash or shares, at the company’s discretion, within 45 days after termination of service, a change in control, death, or disability. Following this award, Sankaran directly holds 2,061 deferred stock units.
Plouffe David reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health, Inc. director David Plouffe received a grant of 681 deferred stock units on July 9, 2026 as board compensation. Each unit represents a right to receive one share of Class A common stock and was valued using the Class A closing price of $31.20 on that date.
The units were issued under the Amended and Restated Deferred Compensation Plan for Directors in lieu of cash retainer payments and are 100% vested on the grant date. They will be settled in cash or Class A shares, at the company’s discretion, within 45 days after specified events such as termination of service, a change in control, death, or disability. Following this grant, Plouffe holds 7,535 deferred stock units directly.
Oscar Health, Inc. director Mario Schlosser reported trust-related transactions in the company’s common stock. A Pizzo-Schlosser Family Dynasty Trust sold a total of 47,500 shares of Class A common stock in open-market trades at weighted average prices of $29.50, $30.80, and $31.65, pursuant to a Rule 10b5-1 trading plan adopted on March 24, 2026.
On the same date, the trust converted 47,500 shares of Class B common stock into 47,500 shares of Class A common stock on a one-to-one basis. After these transactions, the trust holds 43,900 shares of Class A and 538,333 shares of Class B common stock. Schlosser also holds 480,866 Class A and 1,212,293 Class B shares directly, plus additional Class B shares through two other dynasty trusts, and he disclaims beneficial ownership of trust-held shares except to the extent of any pecuniary interest.
Oscar Health, Inc. Chief Executive Officer Mark T. Bertolini reported open-market sales of a total of 1,238,996 shares of Class A Common Stock on June 29–30, 2026. Footnotes explain these sales were made to satisfy tax withholding obligations related to deferred settlement of performance stock units that vested on April 3, 2026, under a pre-arranged Rule 10b5-1 instruction letter entered on November 10, 2025 and amended on March 24, 2026. The reported weighted average sale prices ranged from about $27.78 to $30.61 per share. Following these transactions, Bertolini directly holds 7,751,570 shares of Class A Common Stock, which the disclosure notes includes shares to be issued upon future vesting of restricted stock units.
Oscar Health, Inc. CEO Mark T. Bertolini reported open-market sales of a total of 1,206,310 shares of Class A common stock on June 25–26, 2026 at weighted average prices ranging from $28.06 to $30.17 per share. According to the filing, these transactions represent sales to satisfy tax withholding obligations related to the deferred settlement of performance stock units and time-based restricted stock units that vested on April 3, 2026, and were effected pursuant to a pre-arranged Rule 10b5-1 instruction letter. Following these transactions, Bertolini continues to hold at least 8,990,566 shares of Class A common stock directly.
Oscar Health director Mario Schlosser reported a mix of option exercises, conversions, and open-market sales of Class A common stock. Family dynasty trusts associated with him sold an aggregate of 1,027,500 shares at weighted average prices between about $28.95 and $30.09, and he has disclaimed beneficial ownership in those trust holdings except for any pecuniary interest.
On the same date, he exercised and converted derivative securities into 2,347,500 shares, including 660,000 shares from a fully vested stock option with a $9.75 exercise price. After these direct transactions, he reports holding 480,866 Class A shares and 2,092,293 Class B shares directly. The filing states that the transactions were effected under a Rule 10b5-1 trading plan adopted on March 24, 2026.
Lang Laura W reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health, Inc. director Laura W. Lang received a grant of 8,475 restricted stock units (RSUs) of Class A common stock at no cash cost. Each RSU represents one share and vests on the earlier of the one-year anniversary of the grant date or the next annual stockholder meeting, subject to continued service. Vested RSUs are settled in shares after separation, death, disability, or within days following a change in control. After this award, Lang directly holds 82,840 shares, including these RSUs.
Plouffe David reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health, Inc. reported that director David Plouffe received a grant of 8,475 restricted stock units (RSUs) tied to its Class A common stock. Following this equity award, his reported direct holdings total 137,121 shares.
The RSUs vest on the earlier of the one-year anniversary of the grant date or the next annual stockholders’ meeting, assuming continued service. Once vested, they are settled in Class A shares upon specified events such as separation from service, death, disability, or a change in control.
Sankaran Sid reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health, Inc. director Sid Sankaran reported an equity award and updated holdings. He received 8,475 shares of Class A common stock as a grant of restricted stock units (RSUs) at no cash cost, bringing his directly held shares to 22,609.
Each RSU represents one share of Class A common stock and vests on the earlier of the one-year anniversary of the grant date or the next annual stockholder meeting, subject to continued service. Vested RSUs settle in shares after certain separation, disability, death, or change-in-control triggers.
Separately, 795,686 shares of Class A common stock are held indirectly by Victoria Family LLC, which is wholly owned by fiduciaries of The Victoria 2020 Trust. Sankaran acts as investment adviser to the trust and disclaims beneficial ownership of those shares except for his pecuniary interest.
Oscar Health director William Gassen received an equity award of 8,475 restricted stock units (RSUs) of Class A common stock. The grant has no cash exercise price and is part of his director compensation, not an open-market purchase.
The RSUs vest on the earlier of the one-year anniversary of the grant date or the next annual stockholder meeting, as long as he remains in service through that date. Once vested, shares will be delivered after separation, death, disability, or within a few days following a change in control, under the timing rules described. After this grant, he holds 82,840 shares directly.
WITTMAN VANESSA AMES reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health director Vanessa Ames Wittman received a grant of 8,475 restricted stock units (RSUs) of Class A common stock as equity compensation. The award was made at no cash cost per share and is structured as RSUs rather than an open-market purchase.
The RSUs vest on the earlier of the one-year anniversary of the grant date or the next annual meeting of stockholders, provided she continues serving through that date. Once vested, they are settled in Class A shares after separation, death, disability, or shortly following a change in control, as specified.
Following this grant, Wittman directly holds 137,121 shares (including RSUs) of Oscar Health Class A common stock.
Oscar Health, Inc. Chief Accounting Officer Victoria Baltrus reported selling 1,523 shares of Class A common stock on June 2, 2026 in two open-market transactions at weighted-average prices around $21–$23. According to the disclosure, these sales were made under a Rule 10b5-1 instruction letter to satisfy tax withholding obligations from previously vested equity awards. After the transactions, she continues to directly hold about 214,589 shares, so the sale represents a small portion of her overall position.
Oscar Health director Mario Schlosser reported selling a total of 34,120 shares of Class A common stock on June 2, 2026 in two open-market transactions. He sold 9,668 shares at a weighted average price of $22.45 and 24,452 shares at a weighted average price of $21.74.
According to the footnotes, these sales were effected under a Rule 10b5-1 instruction letter entered into on August 8, 2025, to satisfy his tax withholding obligations arising from the vesting of previously granted equity awards. The prices reflect multiple trades within stated ranges on that date.
Oscar Health, Inc. Chief Legal Officer Adam McAnaney reported selling a total of 9,859 shares of Class A common stock in two open-market transactions. One sale covered 2,794 shares at a weighted average price of about $22.45 per share, and the other covered 7,065 shares at about $21.74 per share. According to the disclosure, these sales were carried out under a pre-arranged Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy tax withholding obligations upon the vesting of previously granted equity awards. The prices reflected multiple trades within ranges of $21.03 to $22.02 and $22.03 to $22.96 per share.
Oscar Health, Inc. President, Oscar Insurance, Janet Liang reported open-market sales of a total of 12,475 shares of Class A common stock on June 2, 2026. The transactions were executed at weighted average prices of about $21.74 and $22.45 per share.
According to the disclosure, these sales were effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy her tax withholding obligations arising from the vesting of previously granted equity awards. The filing notes that her holdings include shares to be issued upon vesting of restricted stock units.
Oscar Health, Inc. Chief Financial Officer Richard Scott Blackley reported open‑market sales of 31,683 shares of Class A Common Stock on June 2, 2026. The shares were sold in two transactions of 8,977 shares at $22.45 and 22,706 shares at $21.74 per share. A footnote states the sales were effected under a Rule 10b5‑1 instruction letter entered into on August 8, 2025 to satisfy the reporting person’s tax withholding obligations upon vesting of previously granted equity awards. The filing also notes 75,000 shares held indirectly by the MQB Irrevocable Trust.
Oscar Health Chief Financial Officer Richard Scott Blackley sold 110,000 shares of Class A Common Stock in an open-market transaction at a weighted average price of $25.03 per share. The sale was carried out pursuant to a Rule 10b5-1 trading plan adopted on February 12, 2026, indicating it was pre-arranged. After the sale, he holds 1,106,660 shares directly, and an additional 75,000 shares are held indirectly by the MQB Irrevocable Trust, which includes shares to be issued upon vesting of restricted stock units.
Oscar Health, Inc. Chief Financial Officer Richard Scott Blackley reported open‑market sales of 100,000 shares of Class A Common Stock on May 14, 2026. The filing shows two sale tranches: 8,741 shares at a weighted average price of $23.79 and 91,259 shares at a weighted average price of $23.10.
These transactions were effected under a Rule 10b5‑1 trading plan adopted on February 12, 2026 and executed through multiple trades within price ranges of $22.68–$23.67 and $23.68–$24.09. Blackley also reported indirect ownership of 75,000 shares held by the MQB Irrevocable Trust, alongside his remaining direct holdings.
Sankaran Sid reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health, Inc. director Sid Sankaran received a grant of 1,203 deferred stock units, each representing the right to one share of Oscar Health Class A common stock. The units were issued in lieu of cash retainer payments for board service, using the $14.54 April 9, 2026 closing share price to calculate the grant size.
The deferred stock units are 100% vested on the grant date and will be settled in either cash or Class A shares, at the company’s discretion, within 45 days after the earliest of termination of service, a change in control, death, or disability.
Gassen William reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health director William Gassen received 1,418 deferred stock units as board compensation. Each unit represents one share of Class A common stock, valued at $14.54 based on the share price on April 9, 2026. He now holds 6,387 deferred stock units, which will be settled in cash or stock after specified service-ending events.
BOYD JEFFERY H reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health, Inc. director Jeffery H. Boyd received a grant of 3,610 deferred stock units as compensation for board service. Each unit represents the right to receive one share of Class A common stock and was valued at $14.54, the closing share price on April 9, 2026.
The grant was taken in lieu of cash retainer payments under the company’s deferred compensation plan for directors. The deferred stock units will be settled in cash or shares, at the company’s discretion, within 45 days after events such as termination of service, a change in control, death, or disability. Following this grant, Boyd holds 69,858 deferred stock units directly.
Plouffe David reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health, Inc. director David Plouffe received a grant of 1,461 deferred stock units as board compensation, based on the Class A common stock closing price of $14.54 on April 9, 2026. Each unit represents one share and is 100% vested on the grant date. Following this award, he holds 6,854 deferred stock units directly. These units will be settled in cash or shares, at the company’s discretion, within 45 days after termination of service, a change in control, death, or disability.
Oscar Health, Inc. Chief Executive Officer Mark T. Bertolini reported equity compensation activity and a share purchase. On April 3, 2026, performance stock units covering 5,733,334 shares vested and were exercised at $0.00, delivering the same number of Class A shares based on stock price targets.
On April 6, 2026, the company withheld 1,000,001 Class A shares at $11.92 per share to satisfy tax obligations on a portion of the vested PSUs. That same day, Bertolini purchased 1,000,000 Class A shares from the issuer in a private placement at $11.92 per share. Following these transactions, he directly holds 10,196,876 Class A shares. Future settlements of remaining PSUs and related tax-covering sales will occur under a pre-arranged Rule 10b5-1 instruction letter.
Oscar Health, Inc. Chief Financial Officer Richard Scott Blackley reported bona fide gifts of a total of 225,000 shares of Class A Common Stock on March 12, 2026. These were coded as gift transfers with a price of $0.00 per share, meaning no sale proceeds were received.
Following these gifts, he holds 1,316,660 shares of Class A Common Stock directly. In addition, 75,000 shares are held indirectly through the MQB Irrevocable Trust. According to the disclosure, the gifted shares went to an irrevocable trust for the benefit of a family member who shares his household.
Oscar Health, Inc. reported that executive Janet Liang, President, Oscar Insurance, received a grant of 106,458 shares of Class A common stock as restricted stock units at $0.00 per share. These RSUs will vest quarterly in 12 equal installments beginning on June 1, 2026, contingent on her continued service. On the same day, she sold 7,453 shares of Class A common stock in an open-market transaction at a weighted average price of $13.39 per share under a pre-arranged Rule 10b5-1 instruction, solely to cover tax withholding on previously vested equity awards. After these transactions, she directly holds 271,532 shares of Class A common stock.
Bertolini Mark T reported acquisition or exercise transactions in this Form 4 filing.
Oscar Health, Inc. reported that Chief Executive Officer Mark T. Bertolini received an award of 1,596,877 shares of Class A common stock in the form of restricted stock units at a price of $0.00 per share. These units will vest in three equal annual installments beginning on March 2, 2027, as long as he continues serving as CEO or as a board member through each vesting date. After this grant, he beneficially owns 4,463,543 shares of Class A common stock, which includes shares that may be issued upon future vesting of restricted stock units.
Oscar Health, Inc. Chief Accounting Officer Victoria Baltrus reported equity compensation and a related share sale. She acquired 17,300 shares of Class A common stock in the form of restricted stock units that will vest quarterly in 12 equal installments beginning on June 1, 2026, subject to her continuous service. She also sold 4,638 shares of Class A common stock at a weighted average price of $13.39 per share, in transactions executed between $13.00 and $13.85, under a Rule 10b5-1 instruction letter to cover tax withholding from previously vested equity awards. After these transactions, she directly owned 216,112 shares.
Oscar Health, Inc. Chief Legal Officer Adam McAnaney reported two equity transactions in Class A common stock. He received a grant of 67,424 restricted stock units at no cost, which will vest quarterly in 12 equal installments beginning on June 1, 2026, contingent on continued service.
On the same date, he sold 18,710 shares in an open-market transaction at a weighted average price of $13.39 per share, with individual trade prices ranging from $13.00 to $13.85. The sale was executed under a pre-established Rule 10b5-1 instruction letter to cover tax withholding obligations from earlier equity awards. Following these transactions, he directly owns 227,955 shares of Class A common stock, including shares underlying restricted stock units that will be issued upon vesting.
Oscar Health, Inc. President of Technology & CTO Mario Schlosser reported two transactions in Class A common stock. He received 189,141 shares as a grant of restricted stock units at a price of $0.00 per share, which are scheduled to vest quarterly in 12 equal installments beginning on June 1, 2026, subject to his continuous service.
He also sold 24,335 shares at a weighted average price of $13.39 per share under a pre-arranged Rule 10b5-1 instruction letter to cover tax withholding tied to earlier equity awards. Following these transactions, he directly owned 514,986 shares, including shares to be issued upon future vesting of restricted stock units.
Oscar Health, Inc. Chief Financial Officer Richard Scott Blackley reported two transactions in Class A common stock. He acquired 134,847 shares as restricted stock units that will vest quarterly in 12 equal installments beginning on June 1, 2026, subject to continued service. On the same date, he sold 19,221 shares at a weighted average price of $13.39 per share under a pre-arranged Rule 10b5-1 instruction to cover tax withholding on earlier equity awards. After these transactions, he directly owned 1,466,660 shares, including shares to be issued upon future RSU vesting.
Oscar Health director Jeffery H. Boyd reported a new equity-based award tied to his board service. On January 8, 2026, he acquired 3,106 deferred stock units, each representing a right to receive one share of Oscar Health’s Class A common stock. The units were issued under the company’s Amended and Restated Deferred Compensation Plan for Directors, because he chose to receive stock units instead of cash retainer payments. The number of units was calculated using the Class A share closing price of $16.90 on that date. After this grant, Boyd beneficially owned 66,248 derivative securities in the form of deferred stock units, which will be settled in cash or shares, at the company’s discretion, upon termination of service, a change in control, death, or disability, and they are fully vested at grant.
Oscar Health director William Gassen received 1,220 deferred stock units on January 8, 2026, each representing one share of Oscar Health’s Class A common stock. These units were granted under the company’s Amended and Restated Deferred Compensation Plan for Directors, as Mr. Gassen elected to take deferred stock units instead of a cash retainer for his board service.
The units were valued using the Class A common stock closing price of $16.90 on January 8, 2026, which determined how many units were issued. After this grant, Mr. Gassen beneficially owns 4,969 deferred stock units on a direct basis. The units are fully vested at grant and will be settled, in Oscar Health’s discretion, in cash or shares of Class A common stock within 45 days after the earliest of his termination of service, a change in control, death, or disability.
Oscar Health, Inc. director David Plouffe reported an award of deferred stock units as part of his board compensation. On January 8, 2026, he received 1,257 deferred stock units, each representing the right to receive one share of Oscar Health’s Class A common stock. The award was valued using the closing stock price of $16.90 per share on that date, which was used to calculate how many units he received in lieu of a cash retainer.
After this grant, Plouffe beneficially owns 5,393 deferred stock units, held directly. These units are fully vested on the grant date and will be settled, at the company’s discretion, in cash or Class A shares within 45 days after the earliest of his termination of service, a change in control, death, or disability.
Oscar Health, Inc. director and President of Technology & CTO Mario Schlosser reported a planned share sale. On January 8, 2026, he converted 23,038 shares of Class B common stock into 23,038 shares of Class A common stock at an exercise price of $0.00, then sold 23,038 Class A shares at $17.65 per share. The filing notes that the transaction was carried out under a Rule 10b5-1 trading plan adopted on September 23, 2025, which is a pre-arranged program for selling shares.
After these transactions, Schlosser directly owned 350,180 shares of Class A common stock. In addition, Class B shares held by three dynasty trusts associated with him represent 333,333, 633,333, and 333,333 shares of Class A common stock on a one-to-one conversion basis, and he disclaims beneficial ownership of those trust-held shares except to the extent of any pecuniary interest.
Oscar Health President of Technology & CTO Mario Schlosser reported converting and selling shares of the company’s stock. On January 6, 2026, he converted 76,962 shares of Class B common stock into 76,962 shares of Class A common stock and then sold 76,962 Class A shares at a weighted average price of $17.01, with individual sale prices ranging from $17.00 to $17.05. The transaction was effected under a Rule 10b5-1 trading plan adopted on September 23, 2025.
Following these transactions, Schlosser directly holds 350,180 shares of Class A common stock and 1,455,331 shares of Class B common stock. Additional Class B shares are held indirectly through three dynasty trusts in amounts of 333,333, 633,333, and 333,333 shares, each convertible into an equal number of Class A shares. Schlosser disclaims beneficial ownership of the trust-held shares except to the extent of any pecuniary interest.
Oscar Health insider activity: A director and President of Technology & CTO of Oscar Health, Inc. reported pre-planned trades in Class A common stock under a Rule 10b5-1 trading plan adopted on September 23, 2025. On January 2, 2026, he converted 59,800 shares of Class B common stock into Class A stock and then sold 137,933 Class A shares at a weighted average price of $15.02. On January 5, 2026, he converted an additional 86,893 Class B shares into Class A stock and sold 96,928 Class A shares at a weighted average price of $15.64. After these transactions, he directly beneficially owned 350,180 shares of Class A common stock and continued to hold additional economic interests through convertible Class B shares and family trusts as described. The filing notes that Class B shares are convertible one-for-one into Class A and will mandatorily convert after a specified period or upon certain events.