Direct Digital Holdings's three largest insider shareholders as of September 29, 2026 are W Keith Smith (President, 8.31K shares), Mark D Walker (Chairman And Ceo, 7.86K shares), Mark D Walker (Chairman And Ceo, 2.50K shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Mark D Walker | Chairman And Ceo | 0 | 10,360 | 10,360 | 37.8% | 03 Sep, 2026 |
| 2 | W Keith Smith | President | 1,399 | 8,309 | 9,709 | 35.4% | 17 Nov, 2025 |
| 3 | Antoinette Renee Leatherberry | Director | 2,368 | 0 | 2,368 | 8.6% | 13 Jun, 2025 |
| 4 | Richard Cohen | Director | 2,294 | 0 | 2,294 | 8.4% | 13 Jun, 2025 |
| 5 | Mistelle Locke | Director | 1,284 | 0 | 1,284 | 4.7% | 13 Jun, 2025 |
| 6 | Anu Pillai | Chief Technology Officer | 664 | 0 | 664 | 2.4% | 12 Jun, 2025 |
| 7 | Maria Vilchez Lowrey | Chief Growth Officer | 556 | 0 | 556 | 2.0% | 27 Mar, 2025 |
| 8 | Diana P Diaz | Chief Financial Officer | 153 | 0 | 153 | 0.6% | 18 Oct, 2024 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 01 Sep, 2026 | Mark D Walker | Chairman And Ceo | Disposed S | 1,636 | $2.06 | $3.37K | 8,364 | Indirect |
| 02 Sep, 2026 | Mark D Walker | Chairman And Ceo | Disposed S | 500 | $1.90 | $950 | 7,864 | Indirect |
| 27 Aug, 2026 | Mark D Walker | Chairman And Ceo | Acquired C | 10,000 | — | — | 10,000 | Indirect |
| 27 Aug, 2026 | Mark D Walker | Chairman And Ceo | Disposed C | 10,000 | $0.00 | $0 | 11,279 | Indirect |
| 04 Dec, 2025 | Mark D Walker | Chairman And Ceo | Acquired C | 300,000 | — | — | 5,454 | Indirect |
| 04 Dec, 2025 | Digital Management, Llc Direct | TenPercentOwner | Acquired C | 300,000 | — | — | 5,454 | Direct |
| 04 Dec, 2025 | Digital Management, Llc Direct | TenPercentOwner | Disposed J | 300,000 | $0.00 | $0 | 0 | Direct |
| 04 Dec, 2025 | Mark D Walker | Chairman And Ceo | Disposed C | 300,000 | $0.00 | $0 | 85,110 | Indirect |
| 04 Dec, 2025 | Digital Management, Llc Direct | TenPercentOwner | Disposed C | 300,000 | $0.00 | $0 | 168,629 | Direct |
| 13 Nov, 2025 | W Keith Smith | President | Disposed S | 71,242 | $20.35 | $1.45Mn | 10,127 | Indirect |
| 13 Nov, 2025 | Mark D Walker | Chairman And Ceo | Disposed S | 27,492 | $20.35 | $559.52K | 4,454 | Indirect |
| 14 Nov, 2025 | Mark D Walker | Chairman And Ceo | Disposed S | 245,008 | $11.55 | $2.83Mn | 0 | Indirect |
| 14 Nov, 2025 | W Keith Smith | President | Disposed S | 100,000 | $11.55 | $1.16Mn | 8,309 | Indirect |
| 11 Sep, 2025 | W Keith Smith | President | Acquired C | 600,000 | — | — | 11,422 | Indirect |
| 11 Sep, 2025 | Digital Management, Llc Direct | TenPercentOwner | Acquired C | 872,500 | — | — | 15,862 | Direct |
| 11 Sep, 2025 | Mark D Walker | Chairman And Ceo | Acquired C | 272,500 | — | — | 4,954 | Indirect |
| 11 Sep, 2025 | Digital Management, Llc Direct | TenPercentOwner | Disposed J | 872,500 | $0.00 | $0 | 0 | Direct |
| 11 Sep, 2025 | Digital Management, Llc Direct | TenPercentOwner | Disposed C | 872,500 | $0.00 | $0 | 174,083 | Direct |
| 11 Sep, 2025 | Mark D Walker | Chairman And Ceo | Disposed C | 272,500 | $0.00 | $0 | 90,564 | Indirect |
| 11 Sep, 2025 | W Keith Smith | President | Disposed C | 600,000 | $0.00 | $0 | 83,519 | Indirect |