TOWNSQUARE MEDIA, INC. Form 4 Filings

Townsquare Media, Inc. executive vice president of Finance, Operations and Technology Scott Schatz acquired 1,132 shares of Class A common stock on August 3, 2026 through a dividend reinvestment transaction at $5.94 per share. Following this, he directly holds 72,126 Class A shares, including 42,126 unrestricted shares and 30,000 fully vested options, and 196,846 Class B shares, including 21,846 unrestricted shares and 175,000 fully vested options.

Townsquare Media, Inc. reported that SVP and Chief Accounting Officer Robert L. Worshek acquired 1,558 shares of Class A Common Stock on 2026-07-16 at $4.5700 per share through the company’s 2021 Employee Stock Purchase Plan. After this transaction, his holdings total 7,786 unrestricted shares and 136,494 fully vested stock options, or 144,280 equity interests in aggregate.

Townsquare Media EVP, Finance Op and Tech, Scott Schatz, reported acquiring 2,000 shares of Class A common stock on July 16, 2026 at $4.57 per share under the company’s 2021 Employee Stock Purchase Plan, bringing his direct Class A holdings to 70,994 shares.

His reported Class A position includes 40,994 unrestricted shares and 30,000 fully vested options. His Class B position totals 196,846 interests, comprising 21,846 unrestricted Class B shares and 175,000 fully vested options, all noted as not subject to vesting or transfer restrictions.

Townsquare Media, Inc. COO Erik Hellum sold 35,000 shares of Class A Common Stock in an open-market transaction on June 9, 2026 at a weighted average price of $6.44 per share, with individual trade prices ranging from $6.34 to $6.56.

After the sale, Hellum beneficially owns 914,542 equity-linked interests, including 123,615 Class A shares without vesting or transfer restrictions, 388,733 restricted stock units, and 402,194 fully vested stock options. The sale represents a small portion of his overall position.

Townsquare Media, Inc. executive Robert L. Worshek, SVP and Chief Accounting Officer, reported a mix of equity grants and a share sale. On May 27, 2026, he received a stock award of 34,299 Class A shares that vested immediately at $6.56 per share, plus options for 250,000 and 280,129 shares at a $6.56 exercise price with time-based and performance-based vesting conditions.

On May 28, 2026, he sold 34,299 Class A shares in open-market transactions at a weighted average price of $6.62, within a $6.60–$6.70 range, and held 142,722 shares directly afterward. Footnotes indicate 136,494 options are already fully vested, while additional options vest over three years and upon achieving volume-weighted average price targets of $7.87, $9.18, and $10.50.

Townsquare Media, Inc. executive Claire Marie Yenicay, EVP of Investor Relations and Corporate Communications, reported a mix of stock grant and open-market sales of Class A Common Stock. On May 18, she received a stock award of 53,151 shares that vested immediately at a weighted average price of $6.03 per share.

She then sold 53,151 shares in three open-market transactions: 17,717 shares on May 18 at a weighted average of $6.05, 15,718 shares on May 19 at $6.04, and 19,716 shares on May 20 at $6.09, with each sale executed across multiple trades within disclosed price ranges. After these transactions, she directly holds 222,946 shares of Class A Common Stock, and a footnote states she also holds 205,000 options to purchase Class A Common Stock that are fully vested and unrestricted.

Townsquare Media, Inc. executive Scott Schatz reported a small open-market-style purchase of company stock. He acquired 943 shares of Class A common stock at $6.51 per share in a dividend reinvestment transaction, increasing his direct Class A holdings.

Following this transaction, Schatz directly holds 68,994 Class A shares, including 38,994 unrestricted shares and 30,000 fully vested options to purchase Class A stock. He also directly holds 196,846 Class B shares, including 21,846 unrestricted shares and 175,000 fully vested options to purchase Class B stock, reflecting a substantial ongoing equity position.

Townsquare Media EVP Scott Schatz reported open-market sales of Class A Common Stock. On March 20, he sold 21,090 shares at a weighted average price of $5.02 per share, with trades ranging from $5.00 to $5.13. On March 23, he sold 34,836 shares at a weighted average price of $5.25, within a range of $5.25 to $5.29. These sales total 55,926 shares. After the transactions, he holds 68,051 Class A-related interests, including 38,051 shares and 30,000 fully vested options, and 196,846 Class B-related interests, including 21,846 shares and 175,000 fully vested options.

Townsquare Media EVP Scott Schatz reported a compensation grant and a stock sale in the company’s shares. On March 18, he received 84,906 shares of Class A common stock as a stock award that vests immediately. On March 19, he executed an open-market sale of 28,980 Class A shares at a weighted average price of $5.08 per share, with individual trades ranging from $5.00 to $5.26. After these transactions, he directly holds 123,977 Class A shares, which include 93,977 unrestricted shares and 30,000 fully vested options to purchase Class A stock, as well as 196,846 Class B shares, including 21,846 unrestricted Class B shares and 175,000 fully vested Class B options.

Townsquare Media COO Erik Hellum reported an open-market sale of 20,106 shares of Class A common stock on February 18, 2026 at $6.58 per share.

According to the disclosure, the shares were sold to cover tax withholding after restricted stock units vested, and Hellum held 949,542 shares directly following the transaction.

Townsquare Media executive vice president of finance, operations and technology Scott Schatz reported acquiring 980 shares of Class A common stock at $6.61 per share in a dividend reinvestment transaction on February 2, 2026. Following this, he directly holds 58,051 Class A shares, including 20,000 fully vested options, and 196,846 Class B shares, including 175,000 fully vested options, all without vesting or transfer restrictions.

Townsquare Media, Inc. COO Erik Hellum reported two stock sales in January 2026. On January 16, he sold 7,437 shares of Class A common stock at $5.54 per share, and on January 20 he sold 6,522 shares at $5.57 per share. The filing explains that these shares were sold to cover tax withholding requirements following the vesting of restricted stock units, which is a common administrative transaction.

After these sales, Hellum beneficially owned 969,648 shares of Class A common stock. This total includes 132,553 shares that are not subject to vesting or transfer restrictions, 434,901 restricted stock units, and 402,194 fully vested stock options that are not subject to transfer restrictions. The filing also notes that 52,980 performance-based restricted stock units were cancelled on January 18, 2026.

Townsquare Media reported an equity award for its COO, Erik Hellum. On 01/14/2026 he acquired 92,421 Class A common units at $5.41 per unit and a further 189,368 Class A common units at $5.41. These units are structured as restricted stock units, with some vesting over three years based on continued service and others vesting only if the stock reaches specified volume-weighted average price targets. After these awards, Hellum beneficially owned 1,036,587 Class A common units.

Townsquare Media, Inc. executive Stuart B. Rosenstein, the EVP and CFO, reported new equity awards in the company’s stock-based units. On January 14, 2026, he was granted 110,906 time-based Class A Common Units at $5.41 per unit and 227,242 performance-based Class A Common Units at $5.41 per unit. The time-based units vest in three annual installments of 33.33%, 33.33% and 33.34% following the grant date, subject to continued service.

The performance-based units vest only if a volume weighted average trading price, or VWAP, is achieved over 20 consecutive trading days between the grant date and the third anniversary. VWAP hurdles of $6.49, $7.57 and $8.66 correspond to vesting of 55,402, 73,801 and 98,039 units, respectively, subject to continued service. Following these awards, Rosenstein beneficially owned 1,008,273 Class A Common Units directly and 467,213 shares of Class B common stock, including previously held shares, restricted stock units and vested options.

Townsquare Media, Inc. CEO Bill Wilson, who also serves as a director, reported awards of Class A common units on January 14, 2026. He acquired 231,054 Class A common units as time-based restricted stock units that vest 33.33% on the first anniversary of the grant date, 33.33% on the second, and 33.34% on the third, subject to his continued service.

He also acquired 473,420 performance-based restricted stock units, which vest only if the company’s volume weighted average trading price reaches $6.49, $7.57, and $8.66 for 20 consecutive trading days within three years of the grant date and he remains in service. After these grants, he beneficially owns 3,347,976 Class A common units, including 668,428 shares of Class A common stock, 1,353,940 restricted stock units, and 1,325,608 fully vested stock options.

Townsquare Media director Gary D. Way received a new stock grant for his board service. On 01/14/2026 he was awarded 24,030 shares of Class A common stock as restricted stock, valued at $5.41 per share on the grant date. The award vests in full on the first anniversary of the grant, meaning all of these shares are scheduled to become fully owned at that time if vesting conditions are met.

After this grant, Way beneficially owned a total of 50,712 Class A shares in direct ownership. This total includes 26,682 Class A shares that are already fully vested and not subject to vesting or transfer restrictions.

Townsquare Media director David Lebow received a grant of 24,030 shares of Class A common stock on January 14, 2026 at $5.41 per share. The shares are restricted stock awarded for his service on the company’s board of directors and will vest in full on the first anniversary of the grant.

After this award, he beneficially owns 129,920 shares of Class A common stock. This total includes 95,890 Class A shares that are fully vested and freely transferable, as well as 10,000 stock options to purchase Class A common stock that are fully vested and not subject to transfer restrictions.

Townsquare Media, Inc. director Stephen A. Kaplan reported an equity award of Class A common stock. On 01/14/2026 he received a grant of 24,030 shares of restricted stock at a stated price of $5.41 per share in respect of his services on the company’s Board of Directors. The award is scheduled to vest in full on the first anniversary of the grant, meaning all 24,030 shares are expected to vest at once if conditions are met. Following this grant, Kaplan beneficially owned 232,648 Class A shares, including 208,618 shares that are not subject to vesting or transfer restrictions.

Townsquare Media director Gary Ginsberg reported an equity award of Class A common stock. On January 14, 2026, he received 24,030 shares of restricted Class A common stock at a reference price of $5.41 per share for his service on the company’s board of directors. This restricted stock award vests in full on the first anniversary of the grant.

Following this grant, Ginsberg beneficially owns 129,938 shares of Class A common stock, including 95,908 shares that are fully unrestricted and 10,000 stock options that are fully vested and not subject to transfer restrictions. All reported holdings are listed as directly owned.

Townsquare Media director B. James Ford received a grant of 24,030 shares of Class A common stock on January 14, 2026. This award was granted as restricted stock for his service on the company’s Board of Directors. The restricted shares are scheduled to vest in full on the first anniversary of the grant, meaning all 24,030 shares vest at the same time rather than gradually.

After this grant, Ford beneficially owns 103,790 shares of Townsquare Media Class A common stock in total. That amount includes 79,760 shares that are already fully vested and not subject to vesting or transfer restrictions, with the balance tied to this new restricted stock award.

Townsquare Media, Inc. executive Robert L. Worshek, the company’s SVP and Chief Accounting Officer, reported acquiring additional Class A common stock. On January 8, 2026, he obtained 2,000 shares of Class A common stock at $4.63 per share under the company’s 2021 Employee Stock Purchase Plan.

After this transaction, Worshek beneficially owns 58,924 Class A-related securities directly, including 6,228 shares of Class A common stock that are unrestricted and 52,696 fully vested options to purchase Class A common stock that are not subject to transfer restrictions.

Townsquare Media, Inc. executive Scott Schatz, EVP of Finance, Operations and Technology, reported acquiring additional shares of the company’s Class A common stock. On 01/08/2026, he acquired 2,000 Class A shares at $4.63 per share under the company’s 2021 Employee Stock Purchase Plan. Following this purchase, he beneficially owns 57,071 Class A shares, which include 37,071 shares without vesting or transfer restrictions and 20,000 fully vested options to purchase Class A shares. He also holds 196,846 Class B shares, consisting of 21,846 unrestricted Class B shares and 175,000 fully vested options to purchase Class B shares, all reported as directly owned.

Townsquare Media EVP and CFO Stuart B. Rosenstein acquired 2,000 shares of Class A common stock of Townsquare Media, Inc. on 01/08/2026 under the company’s 2021 Employee Stock Purchase Plan at a price of $4.63 per share. Following this purchase, he beneficially owns 670,125 shares of Class A common stock, which include 121,721 unrestricted shares, 208,079 restricted stock units, and 340,325 fully vested stock options. He also beneficially owns 467,213 shares of Class B common stock, consisting of 117,213 unrestricted shares and 350,000 fully vested stock options.

Townsquare Media, Inc. reported an insider equity transaction by its Chief Operating Officer. On 12/29/2025, the COO sold 5,693 shares of Class A common stock at $5.061 per share. The filing explains that these shares were sold to cover tax withholding requirements following the vesting of restricted stock units, meaning the transaction was tied to equity compensation rather than an open-market discretionary sale.

After this transaction, the COO beneficially owned a total of 754,798 Class A-related interests, consisting of 110,477 shares of Class A common stock without vesting or transfer restrictions, 242,127 restricted stock units, and 402,194 fully vested stock options to purchase Class A common stock that are not subject to transfer restrictions. All reported holdings are listed as directly owned.

Townsquare Media (TSQ) executive Scott Schatz, EVP, Finance Op and Tech, reported a purchase of 855 shares of Class A common stock at $6.299 on 11/03/2025. The filing states the shares were acquired in a dividend reinvestment transaction.

Following the transaction, beneficial ownership is 54,920 Class A (including 34,920 shares not subject to restrictions and 20,000 fully vested options) and 196,846 Class B (including 21,846 shares not subject to restrictions and 175,000 fully vested options). Ownership is reported as Direct.