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Direct Digital Holdings, Inc.·4

Jun 29, 5:10 PM ET

Pillai Anu 4

4 · Direct Digital Holdings, Inc. · Filed Jun 29, 2026

Research Summary

AI-generated summary of this filing

Updated

Direct Digital (DRCT) CTO Anu Pillai Exercises RSUs, Receives Award

What Happened

  • Anu Pillai, Chief Technology Officer of Direct Digital Holdings (DRCT), reported multiple restricted-stock unit (RSU) conversions/vestings, related tax-withholding share dispositions, and a new RSU award. Key items: vest/convert events on Jan 24, Mar 20 and Apr 1, 2026 and a grant recorded on Mar 24, 2026 for 4,375 shares (reported as acquired at $0.00). Several shares were withheld to satisfy tax liabilities (small cash values reported).

Key Details

  • Transaction types: M = exercise/conversion of derivative (RSU vesting/conversion); F = withholding to pay taxes; A = grant/award.
  • Dates and reported movements:
    • 2026-01-24: 102 RSUs vested/converted (derivative); 36 shares withheld for taxes at $16.48 per share (proceeds reported = $593).
    • 2026-03-20: 10 RSUs vested/converted; 5 shares withheld at $3.32 (proceeds = $17).
    • 2026-03-24: Grant/award of 4,375 RSUs recorded as acquired at $0.00.
    • 2026-04-01: 33 RSUs vested/converted; 12 shares withheld at $3.34 (proceeds = $40).
    • Some derivative conversions are reported with $0.00 as the price (typical for RSU-to-share conversions).
  • Shares owned after the reported transactions: the filing does not list a total beneficial ownership amount; reported figures have been adjusted to reflect a 55-for-1 reverse split (Jan 2026) and a subsequent 4-for-1 reverse split (Apr 2026).
  • Footnotes of note:
    • F4: the listed disposals (F) represent shares withheld to satisfy tax liabilities on RSU vesting.
    • F5/F6/F8: the RSU grants and vesting schedules were previously reported in larger pre-split amounts; current counts adjusted for the reverse splits.
  • Timeliness: This Form 4 discloses delinquent transactions that were not timely reported due to an administrative oversight.

Context

  • These were not open-market sales or purchases but internal equity compensation events: RSUs vesting/convertions and a grant. The small “disposals” are tax-withholding shares, not market sales signaling a change in sentiment.
  • For retail investors: such filings are routine for executives receiving compensation; purchases are generally more informative about personal conviction than routine vesting or tax withholding.

Insider Transaction Report

Form 4
Period: 2026-01-24
Direct Digital Holdings, Inc.DRCT
Pillai Anu
Chief Technology Officer
Transactions
  • Exercise/Conversion

    Class A Common Stock, par value $0.001 per share

    [F1][F2]
    2026-01-24+102→ 199 total
  • Tax Payment

    Class A Common Stock, par value $0.001 per share

    [F3][F4]
    2026-01-24$16.48/sh−36$593→ 163 total
  • Exercise/Conversion

    Class A Common Stock, par value $0.001 per share

    [F3][F2]
    2026-03-20+10→ 173 total
  • Tax Payment

    Class A Common Stock, par value $0.001 per share

    [F3][F4]
    2026-03-20$3.32/sh−5$17→ 168 total
  • Exercise/Conversion

    Class A Common Stock, par value $0.001 per share

    [F3][F2]
    2026-04-01+33→ 201 total
  • Tax Payment

    Class A Common Stock, par value $0.001 per share

    [F3][F4]
    2026-04-01$3.34/sh−12$40→ 189 total
  • Exercise/Conversion

    Restricted Stock Units

    [F2][F5]
    2026-01-24−102→ 0 total
    → Class A Common Stock, par value $0.001 per share (102 underlying)
  • Exercise/Conversion

    Restricted Stock Units

    [F2][F6]
    2026-03-20−10→ 0 total
    → Class A Common Stock, par value $0.001 per share (10 underlying)
  • Award

    Employee Stock Options (right to buy)

    [F3][F7]
    2026-03-24+4,375→ 4,375 total
    Exercise: $3.32Exp: 2036-03-24→ Class A Common Stock, par value $0.001 per share (4,375 underlying)
  • Exercise/Conversion

    Restricted Stock Units

    [F2][F8]
    2026-04-01−33→ 68 total
    → Class A Common Stock, par value $0.001 per share (33 underlying)
Footnotes (8)
  • [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.
Signature
/s/ Mark Walker, attorney-in-fact for Anu Pillai|2026-06-29

Documents

1 file
  • 4
    wk-form4_1782767399.xmlPrimary

    FORM 4