Direct Digital (DRCT) CTO gains options, nets shares after RSU vesting

Filing Impact

(Neutral)

Filing Sentiment

(Neutral)

Form Type

Rhea-AI Filing Summary

Direct Digital Holdings Chief Technology Officer Anu Pillai reported routine equity compensation activity, mainly RSU vesting and a new stock option grant. On January 24, 2026, March 20, 2026, and April 1, 2026, restricted stock units converted into a total of 145 shares of Class A common stock, with 53 shares withheld to cover tax liabilities rather than sold on the market.

Separately, on March 24, 2026, Pillai received 4,375 employee stock options with a $3.32 exercise price, scheduled to vest in three equal annual installments beginning on March 24, 2027 and expiring on March 24, 2036. After the latest reported transaction, Pillai directly holds 201 shares of Class A common stock. All share and option amounts were adjusted to reflect a 55-to-1 reverse stock split on January 12, 2026 and a 4-to-1 reverse stock split on April 27, 2026.

Insider Trade Summary

145 shares exercised/converted

Mixed 10 txns

Insider Pillai Anu

Role Chief Technology Officer

Type	Security	Shares	Price	Value
Exercise	Restricted Stock Units	33	$0.00	--
Exercise	Class A Common Stock, par value $0.001 per share	33	$0.00	--
Tax Withholding	Class A Common Stock, par value $0.001 per share	12	$3.34	$40.08
Grant/Award	Employee Stock Options (right to buy)	4,375	$0.00	--
Exercise	Restricted Stock Units	10	$0.00	--
Exercise	Class A Common Stock, par value $0.001 per share	10	$0.00	--
Tax Withholding	Class A Common Stock, par value $0.001 per share	5	$3.32	$16.60
Exercise	Restricted Stock Units	102	$0.00	--
Exercise	Class A Common Stock, par value $0.001 per share	102	$0.00	--
Tax Withholding	Class A Common Stock, par value $0.001 per share	36	$16.48	$593.28

Holdings After Transaction: Restricted Stock Units — 68 shares (Direct, null); Class A Common Stock, par value $0.001 per share — 201 shares (Direct, null); Employee Stock Options (right to buy) — 4,375 shares (Direct, null)

Footnotes (1)

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. 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. The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split. Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction 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. 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. This option is scheduled to vest in three equal annual installments beginning on March 24, 2027. 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.

Key Figures

RSUs converted: 145 shares Shares withheld for taxes: 53 shares Post-transaction holdings: 201 shares +4 more

7 metrics

RSUs converted 145 shares Restricted stock units converting into Class A common on Jan 24, Mar 20, and Apr 1, 2026

Shares withheld for taxes 53 shares Tax-withholding dispositions at $16.48, $3.32, and $3.34 per share on 2026 dates

Post-transaction holdings 201 shares Direct Class A common stock held after April 1, 2026 transaction

New stock options granted 4,375 options Employee stock options granted Mar 24, 2026 with future vesting

Option exercise price $3.32 per share Conversion or exercise price for employee stock options granted Mar 24, 2026

Option expiration March 24, 2036 Expiration date for 4,375 employee stock options

Reverse stock splits 55-to-1 and 4-to-1 Reverse stock splits on Jan 12, 2026 and Apr 27, 2026 adjusting all share data

Key Terms

Restricted stock units, reverse stock split, Employee Stock Options (right to buy), tax liabilities, +1 more

5 terms

Restricted stock units financial

"Restricted stock units convert into shares of the Company's Class A Common Stock"

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

reverse stock split financial

"effected a 55-to-1 reverse stock split and subsequently a 4-to-1 reverse stock split"

A reverse stock split is when a company reduces the number of its shares outstanding, making each share more valuable. For example, if you own 100 shares worth $1 each, a 1-for-10 reverse split would turn your 100 shares into 10 shares worth $10 each. Companies often do this to boost their stock price and appear more stable to investors.

Employee Stock Options (right to buy) financial

"Employee Stock Options (right to buy) with a conversion or exercise price of 3.3200"

tax liabilities financial

"Represents shares withheld to satisfy tax liabilities associated with the reported vesting"

Change in Control financial

"vesting will be accelerated upon certain termination events and upon a "Change in Control""

A "change in control" occurs when the ownership or management of a company shifts significantly, such as through a merger, acquisition, or sale of a large part of its assets. This change can impact how the company is run and may influence its future direction. For investors, it matters because it can affect the company's stability, strategy, and value, often signaling potential changes in investment risk or opportunity.

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Form 4 Insider Transactions: What Each Field Means →

Available on EDGAR 06/29/2026 - 05:10 PM Accepted by SEC EDGAR 06/29/2026 - 05:10 PM

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Pillai Anu

(Last)

(First)

(Middle)

1177 WEST LOOP SOUTH, SUITE 1310

(Street)

HOUSTON

TEXAS

77027

(City)

(State)

(Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Direct Digital Holdings, Inc. [ DRCT ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director	10% Owner
X	Officer (give title below)	Other (specify below)
	Chief Technology Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
01/24/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Class A Common Stock, par value $0.001 per share	01/24/2026		M		102⁽¹⁾	A	⁽²⁾	199⁽¹⁾	D
Class A Common Stock, par value $0.001 per share	01/24/2026		F		36⁽³⁾⁽⁴⁾	D	$16.48⁽³⁾	163	D
Class A Common Stock, par value $0.001 per share	03/20/2026		M		10⁽³⁾	A	⁽²⁾	173	D
Class A Common Stock, par value $0.001 per share	03/20/2026		F		5⁽³⁾⁽⁴⁾	D	$3.32⁽³⁾	168	D
Class A Common Stock, par value $0.001 per share	04/01/2026		M		33⁽³⁾	A	⁽²⁾	201	D
Class A Common Stock, par value $0.001 per share	04/01/2026		F		12⁽³⁾⁽⁴⁾	D	$3.34⁽³⁾	189	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
Restricted Stock Units	⁽²⁾	01/24/2026		M			102⁽⁵⁾	⁽⁵⁾	⁽⁵⁾	Class A Common Stock, par value $0.001 per share	102⁽⁵⁾	$0	0	D
Restricted Stock Units	⁽²⁾	03/20/2026		M			10⁽⁶⁾	⁽⁶⁾	⁽⁶⁾	Class A Common Stock, par value $0.001 per share	10⁽⁶⁾	$0	0	D
Employee Stock Options (right to buy)	$3.32⁽³⁾	03/24/2026		A		4,375⁽³⁾		⁽⁷⁾	03/24/2036	Class A Common Stock, par value $0.001 per share	4,375⁽³⁾	$0	4,375⁽³⁾	D
Restricted Stock Units	⁽²⁾	04/01/2026		M			33⁽⁸⁾	⁽⁸⁾	⁽⁸⁾	Class A Common Stock, par value $0.001 per share	33⁽⁸⁾	$0	68⁽⁸⁾	D

Explanation of Responses:

1. 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.

2. 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.

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

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

5. 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.

6. 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.

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

8. 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.

Remarks:

The Reporting Person is hereby disclosing delinquent transactions reportable on Form 4 that were not reported due to an administrative oversight.

	/s/ Mark Walker, attorney-in-fact for Anu Pillai	06/29/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

FAQ

What did Direct Digital (DRCT) CTO Anu Pillai report in this Form 4?

The filing shows RSU vesting, tax withholding, and a new option grant. Restricted stock units converted into common shares, some shares were withheld for taxes, and 4,375 employee stock options were granted as part of routine equity compensation.

How many Direct Digital (DRCT) shares does Anu Pillai hold after these transactions?

After the latest reported transaction, Pillai directly holds 201 Class A shares. This figure reflects multiple RSU vesting events, related tax-withholding dispositions, and all adjustments for the company’s reverse stock splits described in the footnotes.

What stock options were granted to Anu Pillai by Direct Digital (DRCT)?

Pillai received 4,375 employee stock options at a $3.32 exercise price. The options relate to Class A common stock, vest in three equal annual installments starting March 24, 2027, and are scheduled to expire on March 24, 2036.

How many Direct Digital (DRCT) RSUs vested for Anu Pillai and what happened to them?

A total of 145 restricted stock units converted into Class A common shares. These RSUs vested on January 24, 2026, March 20, 2026, and April 1, 2026, with 53 resulting shares withheld to satisfy tax obligations.

Were Anu Pillai’s Form 4 transactions open-market buys or sales of DRCT stock?

The reported dispositions reflect tax withholding, not open-market sales. Code F entries show shares delivered to cover tax liabilities on RSU vesting, while code M entries show derivative exercises where RSUs converted into common shares at no cash exercise price.

How did Direct Digital’s reverse stock splits affect the numbers in this Form 4?

All reported share and price figures were adjusted for two reverse stock splits. A 55-to-1 split on January 12, 2026 and a 4-to-1 split on April 27, 2026 changed previously reported RSU and option amounts to the smaller figures shown.