Anu Pillai

About Anu Pillai

Anu Pillai is Chief Technology Officer (CTO) of Direct Digital Holdings (DRCT), appointed in March 2021. She brings extensive experience in product development, large-scale IT implementations, program management, software development, system architecture, and cybersecurity, and holds a B.S. in Computer Science and Engineering from Bharathiar University (India) . Pillai was 55 as of the 2025 proxy and 54 as of the 2024 proxy, and has led technology and digital initiatives spanning the U.S., China, Mexico, and India . During her tenure, DRCT faced a May 2024 sell-side volume disruption and reported a net loss of $10.1 million for the six months ended June 30, 2025 with going concern uncertainty; the board sought to increase authorized Class A shares and expand equity capacity to support financing flexibility .

Past Roles

External Roles

No public company directorships or committee roles were disclosed for Pillai in the latest DRCT proxy statements .

Fixed Compensation

Not disclosed. DRCT, as a smaller reporting company, discloses compensation detail for named executive officers (NEOs) only (CEO, President, CFO), and Pillai is not listed as an NEO in 2024 or 2025 proxies .

Performance Compensation

Not disclosed for Pillai. The company describes an annual incentive program (for NEOs) with target bonuses and payout curves tied to revenue and EBITDA (0–150% of target), with no payouts for 2024 performance and 85% of target paid for 2023 (NEOs only) . There is no proxy disclosure confirming Pillai’s participation, targets, weightings, or outcomes .

Equity Ownership & Alignment

• Option grants to Pillai under the 2022 Omnibus Plan have increased since 2024, indicating continued equity-based incentives. DRCT’s plan prohibits repricing without shareholder approval and contains standard vesting mechanics and change-in-control protections .

• Company-wide policies include a clawback policy adopted in 2023 and a prohibition on hedging, short sales, options trading, trading on margin, or pledging of company stock by directors, executive officers, and employees, reinforcing alignment and reducing risk of forced selling .

• DRCT has materially expanded equity capacity: the board sought to increase the Omnibus Plan reserve to 7,500,000 shares in 2025 and pursued approvals to issue up to 50,000,000 Class A shares under an equity reserve facility with New Circle, which may be dilutive and affect market supply dynamics .

Equity awards summary — Pillai (options granted since plan inception):

Vesting and structural terms (company standard):

• Options generally vest in equal annual installments over three years; RSUs vest in equal annual installments over three years (award-agreement standard) .
• Option term up to 10 years (5 years if ISO to 10%+ holders); SARs/other awards per plan agreements .
• Change in control: unassumed awards generally vest; if assumed/continued and the participant is terminated without cause or resigns for good reason within 12 months post-CIC, awards vest in full (plan terms) .
• Repricing of options/SARs prohibited without shareholder approval .

Insider selling/pledging:

• No individual Form 4 activity for Pillai was identified in the filings reviewed; company policy prohibits pledging/hedging by officers, limiting leverage-related selling pressure .

Employment Terms

• No Pillai-specific employment agreement, severance, or change-of-control economics are disclosed in the 2024 or 2025 proxies; those sections cover NEO agreements (CEO/President/CFO) .
• Company-wide clawback policy applies to current/former executive officers in the event of an accounting restatement (NASDAQ/SEC-compliant) .
• Officer exculpation charter amendment was proposed in 2025, aligning liability protections for officers and directors under Delaware law (Section 102(b)(7)) .

Performance & Track Record

• Tenure: CTO since March 2021, overseeing technology roadmap and operations across Colossus SSP and other digital properties, with global team leadership and monetization focus .
• Company context during tenure:
  • A major sell-side partner paused connections in May 2024, reducing volumes; volumes resumed but below prior levels as of Sept 2025, contributing to disruption .
  • DRCT incurred a net loss of $10.1 million for the six months ended June 30, 2025; the 2024 auditor report included a going concern explanatory paragraph .
  • Financing/governance actions included proposals to increase authorized Class A shares to 760,000,000 and protective provisions and voting rights for Series A Preferred (e.g., Independent Director consent on specified actions) .
  • Nasdaq compliance: Panel confirmed equity compliance; exception granted through Jan 30, 2026 to regain bid-price compliance, with a potential reverse split under consideration .

Investment Implications

• Incentive alignment: Pillai’s equity upside appears to be primarily via options (47,465 options granted since plan inception as of March 31, 2025), aligning her incentives with long-term equity value creation; standard 3-year vesting reduces near-term cliff exposure but implies steady vesting cadence that could create periodic liquidity windows if in-the-money .
• Selling pressure/dilution: Company-wide prohibitions on hedging/pledging reduce forced-sale risk for insiders, but broader share issuance capacity (Equity Reserve Facility up to 50,000,000 shares; Omnibus Plan increased to 7,500,000 shares) may contribute to market supply and dilution, potentially pressuring near-term valuations independent of insider activity .
• Retention risk: No Pillai-specific employment/severance/change-of-control terms were disclosed, creating visibility gaps on retention economics; however, plan-level CIC protections for awards may partially mitigate departure risk around corporate events .
• Execution risk: As CTO, Pillai’s effectiveness is tied to stabilizing/rescaling sell-side volumes (Colossus SSP) and technology performance amid disruptions and financing constraints; the going concern context and lender-influenced governance changes heighten the strategic stakes of technology execution under her purview .

Key data sources: Executive biography and age (2024/2025 proxies) **[1880613_0001628280-25-020480_ddh-2025definitiveproxydef.htm:24]** **[1880613_0001628280-24-048082_ddh-def14a.htm:21]**; Pillai option grant counts (2024/2025 proxies) **[1880613_0001628280-24-048082_ddh-def14a.htm:46]** **[1880613_0001628280-25-020480_ddh-2025definitiveproxydef.htm:49]**; plan vesting/terms, CIC, repricing (2025 proxy) **[1880613_0001628280-25-020480_ddh-2025definitiveproxydef.htm:28]** **[1880613_0001628280-25-020480_ddh-2025definitiveproxydef.htm:44]** **[1880613_0001628280-25-020480_ddh-2025definitiveproxydef.htm:45]**; clawback and insider trading policies (2025 proxy) **[1880613_0001628280-25-020480_ddh-2025definitiveproxydef.htm:29]** **[1880613_0001628280-25-020480_ddh-2025definitiveproxydef.htm:20]**; equity plan/share issuance capacity (2025 proxy; 2025 special meeting proxy) **[1880613_0001628280-25-020480_ddh-2025definitiveproxydef.htm:41]** **[1880613_0001880613-25-000112_drct-2025specialmeetingpro.htm:14]** **[1880613_0001880613-25-000112_drct-2025specialmeetingpro.htm:15]**; disruption/loss/governance context (2025 special meeting proxy; 8‑K) **[1880613_0001880613-25-000112_drct-2025specialmeetingpro.htm:9]** **[1880613_0001880613-25-000112_drct-2025specialmeetingpro.htm:11]** **[1880613_0001880613-25-000123_a31-directdigitalholdingsi.htm:7]** **[1880613_0001880613-25-000123_drct-20251014.htm:6]** **[1880613_0001880613-25-000123_a102-amend9xsideletterrega.htm:1]**; Nasdaq compliance status (8‑K) **[1880613_0001880613-25-000136_drct-20251107.htm:2]**.