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Pillai Anu

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34859
SEC CIK
0001896798

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CompanyLast reported asReport datePublished
Direct Digital Holdings, Inc.DRCT · Entity 2630Chief Technology OfficerJanuary 24, 2026June 29, 2026

Disclosed balances

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Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

Direct Digital Holdings, Inc.

Report date January 24, 2026 · Filed June 29, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Class A Common Stock, par value $0.001 per shareSEC Table I · non-derivativeDirect199 Reported balance After 2026-01-24 transaction · row 1 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 1 · 2026-01-24 · Exercise / conversion · Acquired 102 · Balance 199

F1: On January 12, 2026, Direct Digital Holdings, Inc. (the "Company") effected a 55-to-1 reverse stock split (the "January Reverse Stock Split") and subsequently on April 27, 2026, the Company effected a 4-to-1 reverse stock split (the "April Reverse Stock Split," and together with the January Reverse Stock Split, the "Reverse Stock Splits"). The Securities Acquired reported in connection with this transaction have been adjusted to reflect the April Reverse Stock Split and the Amount of Securities Beneficially Owned Following Reported Transaction in connection with this transaction have been adjusted to reflect the Reverse Stock Splits.

F2: Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Class A Common Stock, par value $0.001 per shareSEC Table I · non-derivativeDirect163 Reported balance After 2026-01-24 transaction · row 2 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 2 · 2026-01-24 · Tax withholding · Disposed 36 · Balance 163

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

Class A Common Stock, par value $0.001 per shareSEC Table I · non-derivativeDirect173 Reported balance After 2026-03-20 transaction · row 3 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 3 · 2026-03-20 · Exercise / conversion · Acquired 10 · Balance 173

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F2: Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Class A Common Stock, par value $0.001 per shareSEC Table I · non-derivativeDirect168 Reported balance After 2026-03-20 transaction · row 4 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 4 · 2026-03-20 · Tax withholding · Disposed 5 · Balance 168

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

Class A Common Stock, par value $0.001 per shareSEC Table I · non-derivativeDirect201 Reported balance After 2026-04-01 transaction · row 5 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 5 · 2026-04-01 · Exercise / conversion · Acquired 33 · Balance 201

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F2: Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Class A Common Stock, par value $0.001 per shareSEC Table I · non-derivativeDirect189 Reported balance After 2026-04-01 transaction · row 6 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 6 · 2026-04-01 · Tax withholding · Disposed 12 · Balance 189

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

Restricted Stock UnitsSEC Table II · derivative / convertible securityDirect0 Reported balance After 2026-01-24 transaction · row 7 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 7 · 2026-01-24 · Exercise / conversion · Disposed 102 · Balance 0

F2: Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

F5: On January 24, 2025, the reporting person was granted 102 restricted stock units, vesting on the first anniversary of the grant date conditioned on continued employment as of the vesting date. All of the restricted stock units vested on January 24, 2026. This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Restricted Stock UnitsSEC Table II · derivative / convertible securityDirect0 Reported balance After 2026-03-20 transaction · row 8 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 8 · 2026-03-20 · Exercise / conversion · Disposed 10 · Balance 0

F2: Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

F6: On March 20, 2023, the reporting person was granted 28 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on March 20, 2024, an additional 33% of the restricted stock units vested on March 20, 2025, and the remaining balance of 34% of the restricted stock units vested on March 20, 2026. This grant was previously reported as covering 6,315 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Restricted Stock UnitsSEC Table II · derivative / convertible securityDirect68 Reported balance After 2026-04-01 transaction · row 10 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 10 · 2026-04-01 · Exercise / conversion · Disposed 33 · Balance 68

F2: Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

F8: On April 1, 2025, the reporting person was granted 101 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on April 1, 2026, an additional 33% of the restricted stock units will vest on April 1, 2027, and the remaining balance of 34% of the restricted stock units will vest on April 1, 2028. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan). This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Employee Stock Options (right to buy)SEC Table II · derivative / convertible security · Conversion / exercise price $3.32 · Expires 2036-03-24Direct4,375 Reported balance After 2026-03-24 transaction · row 9 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 9 · 2026-03-24 · Grant · Acquired 4,375 · Balance 4,375

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F7: This option is scheduled to vest in three equal annual installments beginning on March 24, 2027.

Filing footnotes · ownership attribution and instrument terms

F1: On January 12, 2026, Direct Digital Holdings, Inc. (the "Company") effected a 55-to-1 reverse stock split (the "January Reverse Stock Split") and subsequently on April 27, 2026, the Company effected a 4-to-1 reverse stock split (the "April Reverse Stock Split," and together with the January Reverse Stock Split, the "Reverse Stock Splits"). The Securities Acquired reported in connection with this transaction have been adjusted to reflect the April Reverse Stock Split and the Amount of Securities Beneficially Owned Following Reported Transaction in connection with this transaction have been adjusted to reflect the Reverse Stock Splits.

F2: Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

F5: On January 24, 2025, the reporting person was granted 102 restricted stock units, vesting on the first anniversary of the grant date conditioned on continued employment as of the vesting date. All of the restricted stock units vested on January 24, 2026. This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F6: On March 20, 2023, the reporting person was granted 28 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on March 20, 2024, an additional 33% of the restricted stock units vested on March 20, 2025, and the remaining balance of 34% of the restricted stock units vested on March 20, 2026. This grant was previously reported as covering 6,315 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F7: This option is scheduled to vest in three equal annual installments beginning on March 24, 2027.

F8: On April 1, 2025, the reporting person was granted 101 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on April 1, 2026, an additional 33% of the restricted stock units will vest on April 1, 2027, and the remaining balance of 34% of the restricted stock units will vest on April 1, 2028. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan). This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

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Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
April 01, 2026 Filed Jun 29, 2026 21:10 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 33 $0.00 $0.00
Disclosure

SEC source: 0001896798-26-000002 · wk-form4_1782767399.xml · derivative · entry 10

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 68

Underlying: Class A Common Stock, par value $0.001 per share · 33 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

F8 · shares: On April 1, 2025, the reporting person was granted 101 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on April 1, 2026, an additional 33% of the restricted stock units will vest on April 1, 2027, and the remaining balance of 34% of the restricted stock units will vest on April 1, 2028. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan). This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F8 · derivative.exercise_date: On April 1, 2025, the reporting person was granted 101 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on April 1, 2026, an additional 33% of the restricted stock units will vest on April 1, 2027, and the remaining balance of 34% of the restricted stock units will vest on April 1, 2028. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan). This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F8 · derivative.expiration_date: On April 1, 2025, the reporting person was granted 101 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on April 1, 2026, an additional 33% of the restricted stock units will vest on April 1, 2027, and the remaining balance of 34% of the restricted stock units will vest on April 1, 2028. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan). This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F8 · derivative.underlying_shares: On April 1, 2025, the reporting person was granted 101 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on April 1, 2026, an additional 33% of the restricted stock units will vest on April 1, 2027, and the remaining balance of 34% of the restricted stock units will vest on April 1, 2028. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan). This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F8 · balance_after: On April 1, 2025, the reporting person was granted 101 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on April 1, 2026, an additional 33% of the restricted stock units will vest on April 1, 2027, and the remaining balance of 34% of the restricted stock units will vest on April 1, 2028. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan). This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Read SEC document
April 01, 2026 Filed Jun 29, 2026 21:10 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock, par value $0.001 per share 12 $3.34 $40.08
Disclosure

SEC source: 0001896798-26-000002 · wk-form4_1782767399.xml · nonDerivative · entry 6

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 189

F3 · shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

F3 · price: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Read SEC document
April 01, 2026 Filed Jun 29, 2026 21:10 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock, par value $0.001 per share 33 Not disclosed Not disclosed
Disclosure

SEC source: 0001896798-26-000002 · wk-form4_1782767399.xml · nonDerivative · entry 5

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 201

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F2 · price: Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Read SEC document
March 24, 2026 Filed Jun 29, 2026 21:10 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantEmployee Stock Options (right to buy) · Derivative 4,375 $0.00 Strike: $3.32 $0.00
Disclosure

SEC source: 0001896798-26-000002 · wk-form4_1782767399.xml · derivative · entry 9

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,375

Underlying: Class A Common Stock, par value $0.001 per share · 4,375 shares

Expires 2036-03-24

F3 · derivative.exercise_price: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F3 · shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F7 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on March 24, 2027.

F3 · derivative.underlying_shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F3 · balance_after: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Read SEC document
March 20, 2026 Filed Jun 29, 2026 21:10 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 10 $0.00 $0.00
Disclosure

SEC source: 0001896798-26-000002 · wk-form4_1782767399.xml · derivative · entry 8

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class A Common Stock, par value $0.001 per share · 10 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

F6 · shares: On March 20, 2023, the reporting person was granted 28 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on March 20, 2024, an additional 33% of the restricted stock units vested on March 20, 2025, and the remaining balance of 34% of the restricted stock units vested on March 20, 2026. This grant was previously reported as covering 6,315 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F6 · derivative.exercise_date: On March 20, 2023, the reporting person was granted 28 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on March 20, 2024, an additional 33% of the restricted stock units vested on March 20, 2025, and the remaining balance of 34% of the restricted stock units vested on March 20, 2026. This grant was previously reported as covering 6,315 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F6 · derivative.expiration_date: On March 20, 2023, the reporting person was granted 28 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on March 20, 2024, an additional 33% of the restricted stock units vested on March 20, 2025, and the remaining balance of 34% of the restricted stock units vested on March 20, 2026. This grant was previously reported as covering 6,315 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F6 · derivative.underlying_shares: On March 20, 2023, the reporting person was granted 28 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on March 20, 2024, an additional 33% of the restricted stock units vested on March 20, 2025, and the remaining balance of 34% of the restricted stock units vested on March 20, 2026. This grant was previously reported as covering 6,315 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Read SEC document
March 20, 2026 Filed Jun 29, 2026 21:10 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock, par value $0.001 per share 5 $3.32 $16.60
Disclosure

SEC source: 0001896798-26-000002 · wk-form4_1782767399.xml · nonDerivative · entry 4

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 168

F3 · shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

F3 · price: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Read SEC document
March 20, 2026 Filed Jun 29, 2026 21:10 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock, par value $0.001 per share 10 Not disclosed Not disclosed
Disclosure

SEC source: 0001896798-26-000002 · wk-form4_1782767399.xml · nonDerivative · entry 3

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 173

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F2 · price: Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Read SEC document
January 24, 2026 Filed Jun 29, 2026 21:10 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 102 $0.00 $0.00
Disclosure

SEC source: 0001896798-26-000002 · wk-form4_1782767399.xml · derivative · entry 7

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class A Common Stock, par value $0.001 per share · 102 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_price: Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

F5 · shares: On January 24, 2025, the reporting person was granted 102 restricted stock units, vesting on the first anniversary of the grant date conditioned on continued employment as of the vesting date. All of the restricted stock units vested on January 24, 2026. This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F5 · derivative.exercise_date: On January 24, 2025, the reporting person was granted 102 restricted stock units, vesting on the first anniversary of the grant date conditioned on continued employment as of the vesting date. All of the restricted stock units vested on January 24, 2026. This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F5 · derivative.expiration_date: On January 24, 2025, the reporting person was granted 102 restricted stock units, vesting on the first anniversary of the grant date conditioned on continued employment as of the vesting date. All of the restricted stock units vested on January 24, 2026. This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F5 · derivative.underlying_shares: On January 24, 2025, the reporting person was granted 102 restricted stock units, vesting on the first anniversary of the grant date conditioned on continued employment as of the vesting date. All of the restricted stock units vested on January 24, 2026. This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Read SEC document
January 24, 2026 Filed Jun 29, 2026 21:10 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock, par value $0.001 per share 36 $16.48 $593.28
Disclosure

SEC source: 0001896798-26-000002 · wk-form4_1782767399.xml · nonDerivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 163

F3 · shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

F3 · price: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Read SEC document
January 24, 2026 Filed Jun 29, 2026 21:10 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock, par value $0.001 per share 102 Not disclosed Not disclosed
Disclosure

SEC source: 0001896798-26-000002 · wk-form4_1782767399.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 199

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · shares: On January 12, 2026, Direct Digital Holdings, Inc. (the "Company") effected a 55-to-1 reverse stock split (the "January Reverse Stock Split") and subsequently on April 27, 2026, the Company effected a 4-to-1 reverse stock split (the "April Reverse Stock Split," and together with the January Reverse Stock Split, the "Reverse Stock Splits"). The Securities Acquired reported in connection with this transaction have been adjusted to reflect the April Reverse Stock Split and the Amount of Securities Beneficially Owned Following Reported Transaction in connection with this transaction have been adjusted to reflect the Reverse Stock Splits.

F2 · price: Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

F1 · balance_after: On January 12, 2026, Direct Digital Holdings, Inc. (the "Company") effected a 55-to-1 reverse stock split (the "January Reverse Stock Split") and subsequently on April 27, 2026, the Company effected a 4-to-1 reverse stock split (the "April Reverse Stock Split," and together with the January Reverse Stock Split, the "Reverse Stock Splits"). The Securities Acquired reported in connection with this transaction have been adjusted to reflect the April Reverse Stock Split and the Amount of Securities Beneficially Owned Following Reported Transaction in connection with this transaction have been adjusted to reflect the Reverse Stock Splits.

Read SEC document
June 10, 2025 Filed Jun 12, 2025 20:23 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 6,218 $0.00 $0.00
Disclosure

SEC source: 0001880613-25-000031 · wk-form4_1749759807.xml · derivative · entry 3

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class A Common Stock, par value $0.001 per share · 6,218 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F3 · derivative.exercise_date: On June 10, 2022, the reporting person was granted 18,650 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent vested on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units vested on June 10, 2025.

F3 · derivative.expiration_date: On June 10, 2022, the reporting person was granted 18,650 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent vested on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units vested on June 10, 2025.

Read SEC document
June 10, 2025 Filed Jun 12, 2025 20:23 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock, par value $0.001 per share 2,152 $0.56 $1,205.12
Disclosure

SEC source: 0001880613-25-000031 · wk-form4_1749759807.xml · nonDerivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,704

F2 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units for 6,218 shares.

Read SEC document
June 10, 2025 Filed Jun 12, 2025 20:23 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock, par value $0.001 per share 6,218 Not disclosed Not disclosed
Disclosure

SEC source: 0001880613-25-000031 · wk-form4_1749759807.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 23,856

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

Read SEC document
April 01, 2025 Filed Apr 4, 2025 21:48 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantEmployee Stock Options (right to buy) · Derivative 22,500 $0.00 Strike: $0.64 $0.00
Disclosure

SEC source: 0001628280-25-016871 · wk-form4_1743803313.xml · derivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,500

Underlying: Class A Common Stock, par value $0.001 per share · 22,500 shares

Expires 2035-04-01

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on April 1, 2026.

Read SEC document
April 01, 2025 Filed Apr 4, 2025 21:48 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantRestricted Stock Units · Derivative 22,500 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-016871 · wk-form4_1743803313.xml · derivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,500

Underlying: Class A Common Stock, par value $0.001 per share · 22,500 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F2 · derivative.expiration_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

Read SEC document
March 20, 2025 Filed Mar 27, 2025 23:55 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 2,105 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-015295 · wk-form4_1743119752.xml · derivative · entry 3

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,105

Underlying: Class A Common Stock, par value $0.001 per share · 2,105 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F4 · derivative.exercise_date: On March 20, 2023, the reporting person was granted 6,315 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on March 20, 2024, an additional 33% of the restricted stock units vested on March 20, 2025, and the remaining balance of 34% of the restricted stock units will vest on March 20, 2026. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F4 · derivative.expiration_date: On March 20, 2023, the reporting person was granted 6,315 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on March 20, 2024, an additional 33% of the restricted stock units vested on March 20, 2025, and the remaining balance of 34% of the restricted stock units will vest on March 20, 2026. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

Read SEC document
March 20, 2025 Filed Mar 27, 2025 23:55 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock, par value $0.001 per share 729 $0.79 $575.91
Disclosure

SEC source: 0001628280-25-015295 · wk-form4_1743119752.xml · nonDerivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,638

F3 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units for 2,105 shares.

Read SEC document
March 20, 2025 Filed Mar 27, 2025 23:55 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock, par value $0.001 per share 2,105 Not disclosed Not disclosed
Disclosure

SEC source: 0001628280-25-015295 · wk-form4_1743119752.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,367

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · balance_after: Due to administrative error, the number of non-derivative securities beneficially owned by the Reporting Person was incorrectly reported as 14,829 instead of 16,262 on a Form 4 filed on June 14, 2024. This column reflects the corrected balance, as effected by the transactions reported on this Form 4.

Read SEC document
January 24, 2025 Filed Jan 28, 2025 21:33 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantEmployee Stock Options (right to buy) · Derivative 22,500 $0.00 Strike: $1.38 $0.00
Disclosure

SEC source: 0001628280-25-002798 · wk-form4_1738100006.xml · derivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,500

Underlying: Class A Common Stock, par value $0.001 per share · 22,500 shares

Expires 2035-01-24

F3 · derivative.exercise_date: This option will vest one year from the date of grant conditioned on continued employment as of the vesting date.

Read SEC document
January 24, 2025 Filed Jan 28, 2025 21:33 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantRestricted Stock Units · Derivative 22,500 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-002798 · wk-form4_1738100006.xml · derivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,500

Underlying: Class A Common Stock, par value $0.001 per share · 22,500 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: Grant of restricted stock units under the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan. The restricted stock units will vest one year from the date of grant conditioned on continued employment as of the vesting date.

F2 · derivative.expiration_date: Grant of restricted stock units under the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan. The restricted stock units will vest one year from the date of grant conditioned on continued employment as of the vesting date.

Read SEC document
June 14, 2024 Filed Jun 15, 2024 01:23 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock 1,822 $2.64 $4,810.08
Disclosure

SEC source: 0001104659-24-071905 · tm2417375-5_4seq1.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,829

F1 · shares: Represents shares withheld to satisfy tax liabilities associated with the previously reported vesting of restricted stock units for 6,216 shares on June 10, 2024.

Read SEC document
June 10, 2024 Filed Jun 12, 2024 23:55 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 6,216 $0.00 $0.00
Disclosure

SEC source: 0001104659-24-070954 · tm2417141-4_4seq1.xml · derivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,218

Underlying: Class A Common Stock, par value $0.001 per share · 6,216 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: On June 10, 2022, the reporting person was granted 18,650 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent vested on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units will vest on June 10, 2025. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F2 · derivative.expiration_date: On June 10, 2022, the reporting person was granted 18,650 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent vested on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units will vest on June 10, 2025. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

Read SEC document
June 10, 2024 Filed Jun 12, 2024 23:55 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock 6,216 Not disclosed Not disclosed
Disclosure

SEC source: 0001104659-24-070954 · tm2417141-4_4seq1.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,651

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

Read SEC document
April 01, 2024 Filed Aug 27, 2024 20:31 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock 617 $15.24 $9,403.08
Disclosure

SEC source: 0001104659-24-093454 · tm2422704-3_4seq1.xml · nonDerivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,868

F3 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units for 2,105 shares.

Read SEC document
March 20, 2024 Filed Aug 27, 2024 20:31 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 2,105 $0.00 $0.00
Disclosure

SEC source: 0001104659-24-093454 · tm2422704-3_4seq1.xml · derivative · entry 3

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,210

Underlying: Class A Common Stock, par value $0.001 per share · 2,105 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F4 · derivative.exercise_date: On March 20, 2023, the reporting person was granted 6,315 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on March 20, 2024, an additional 33% of the restricted stock units will vest on March 20, 2025, and the remaining balance of 34% of the restricted stock units will vest on March 20, 2026. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F4 · derivative.expiration_date: On March 20, 2023, the reporting person was granted 6,315 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on March 20, 2024, an additional 33% of the restricted stock units will vest on March 20, 2025, and the remaining balance of 34% of the restricted stock units will vest on March 20, 2026. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

Read SEC document
March 20, 2024 Filed Aug 27, 2024 20:31 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock 2,105 Not disclosed Not disclosed
Disclosure

SEC source: 0001104659-24-093454 · tm2422704-3_4seq1.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,485

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · balance_after: Due to administrative error, the number of non-derivative securities beneficially owned by the Reporting Person was incorrectly reported as 10,435 instead of 10,380 on a Form 4 filed on March 20, 2024. This column reflects the corrected balance, as effected by the transactions reported on this Form 4.

Read SEC document
March 18, 2024 Filed Mar 20, 2024 21:57 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock 2,961 $28.87 $85,484.07
Disclosure

SEC source: 0001104659-24-036805 · tm249373-4_4seq1.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,435

Read SEC document
March 11, 2024 Filed Mar 13, 2024 21:00 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantClass A Common Stock 9,002 $0.00 $0.00
Disclosure

SEC source: 0001104659-24-033994 · tm248688-1_4seq1.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 13,396

F1 · kind: Represents an award of fully vested shares of the Class A Common Stock, par value $0.001 per share ("Class A Common Stock") of Direct Digital Holdings, Inc. (the "Issuer") granted to the Reporting Person in lieu of annual incentive cash awards earned by the Reporting Person for the fiscal year ended December 31, 2023 under the Issuer's 2022 Omnibus Incentive Plan.

Read SEC document
June 10, 2023 Filed Jun 13, 2023 22:32 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 4,587 $0.00 $0.00
Disclosure

SEC source: 0001104659-23-070910 · tm2318595-4_4seq1.xml · derivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,313

Underlying: Class A Common Stock, par value $0.001 per share · 4,587 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: On June 10, 2022, the reporting person was granted 13,900 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units will vest on June 10, 2025. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F2 · derivative.expiration_date: On June 10, 2022, the reporting person was granted 13,900 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units will vest on June 10, 2025. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

Read SEC document
June 10, 2023 Filed Jun 13, 2023 22:32 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock 4,587 $0.00 $0.00
Disclosure

SEC source: 0001104659-23-070910 · tm2318595-4_4seq1.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,587

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

Read SEC document
June 10, 2023 Filed Aug 24, 2023 01:31 UTC Amendment Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 6,216 $0.00 $0.00
Disclosure

SEC source: 0001104659-23-094629 · tm2324608-1_4aseq1.xml · derivative · entry 3

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,434

Underlying: Class A Common Stock, par value $0.001 per share · 4,587 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F3 · derivative.exercise_date: On June 10, 2022, the reporting person was granted 18,650 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on June 10, 2023, an additional 33% will vest on June 10, 2024, and the remaining balance of 34% of the restricted stock units will vest on June 10, 2025. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F3 · derivative.expiration_date: On June 10, 2022, the reporting person was granted 18,650 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on June 10, 2023, an additional 33% will vest on June 10, 2024, and the remaining balance of 34% of the restricted stock units will vest on June 10, 2025. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

Read SEC document
June 10, 2023 Filed Aug 24, 2023 01:31 UTC Amendment Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock 1,822 $3.25 $5,921.50
Disclosure

SEC source: 0001104659-23-094629 · tm2324608-1_4aseq1.xml · nonDerivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,394

F2 · shares: Due to administrative error, the withholding of shares to satisfy the tax liability incident to the vesting of the restricted stock unit was inadvertently omitted from the original version of this report.

Read SEC document
June 10, 2023 Filed Aug 24, 2023 01:31 UTC Amendment Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock 6,216 Not disclosed Not disclosed
Disclosure

SEC source: 0001104659-23-094629 · tm2324608-1_4aseq1.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,216

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

Read SEC document
March 20, 2023 Filed Mar 22, 2023 21:01 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantEmployee Stock Options (right to buy) · Derivative 6,315 $0.00 Strike: $3.96 $0.00
Disclosure

SEC source: 0001104659-23-035651 · tm2310255-3_4seq1.xml · derivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,315

Underlying: Class A Common Stock, par value $0.001 per share · 6,315 shares

Expires 2033-03-20

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on March 20, 2024.

Read SEC document
March 20, 2023 Filed Mar 22, 2023 21:01 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantRestricted Stock Units · Derivative 6,315 $0.00 $0.00
Disclosure

SEC source: 0001104659-23-035651 · tm2310255-3_4seq1.xml · derivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,315

Underlying: Class A Common Stock, par value $0.001 per share · 6,315 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: The restricted stock units will vest in three equal annual installments, beginning on March 20, 2024. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F2 · derivative.expiration_date: The restricted stock units will vest in three equal annual installments, beginning on March 20, 2024. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

Read SEC document
June 10, 2022 Filed Jun 13, 2022 20:56 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantEmployee Stock Options (right to buy) · Derivative 13,900 $0.00 Strike: $1.62 $0.00
Disclosure

SEC source: 0001104659-22-070578 · tm2218199-1_4seq1.xml · derivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 13,900

Underlying: Class A Common Stock, par value $0.001 per share · 13,900 shares

Expires 2032-06-10

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on June 10, 2023.

Read SEC document
June 10, 2022 Filed Jun 13, 2022 20:56 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantRestricted Stock Units · Derivative 13,900 $0.00 $0.00
Disclosure

SEC source: 0001104659-22-070578 · tm2218199-1_4seq1.xml · derivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 13,900

Underlying: Class A Common Stock, par value $0.001 per share · 13,900 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F2 · derivative.expiration_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

Read SEC document
June 10, 2022 Filed Jun 21, 2022 21:00 UTC Amendment Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantEmployee Stock Options (right to buy) · Derivative 18,650 $0.00 Strike: $1.62 $0.00
Disclosure

SEC source: 0001104659-22-073022 · tm2218805-2_4aseq1.xml · derivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,650

Underlying: Class A Common Stock, par value $0.001 per share · 18,650 shares

Expires 2032-06-10

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on June 10, 2023.

Read SEC document
June 10, 2022 Filed Jun 21, 2022 21:00 UTC Amendment Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantRestricted Stock Units · Derivative 18,650 $0.00 $0.00
Disclosure

SEC source: 0001104659-22-073022 · tm2218805-2_4aseq1.xml · derivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,650

Underlying: Class A Common Stock, par value $0.001 per share · 18,650 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F2 · derivative.expiration_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

Read SEC document

Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.