Dylan Smith
BOXAbout Dylan Smith
Dylan Smith, 39, is Box’s co‑founder and Chief Financial Officer (since April 2005), leading investor relations and all aspects of financial operations; he holds a B.A. in Economics from Duke University . Under Box’s FY2025 performance, revenue reached $1.090 billion (+5% YoY) and non‑GAAP operating income was $303.6 million (28% margin), metrics that directly drive executive pay outcomes . Over the SEC pay‑versus‑performance window, a $100 investment in Box grew to $222 by FY2025, evidencing multi‑year TSR expansion during his tenure .
Past Roles
| Organization | Role | Years | Strategic impact |
|---|---|---|---|
| Box, Inc. | Co‑founder; Chief Financial Officer | 2005–present | Leads investor relations and finance; helped drive non‑GAAP operating margin from 25% (FY2024) to 28% (FY2025) ; supported capital allocation including open‑market repurchases of 7.6M (FY2025), 6.6M (FY2024), and 10.2M (FY2023) shares . |
Fixed Compensation
Multi‑year summary compensation (Dylan Smith):
| Metric ($) | FY2023 | FY2024 | FY2025 |
|---|---|---|---|
| Salary | 411,250 | 386,042 | 382,500 |
| Stock Awards | 4,827,900 | 4,344,450 | 4,451,200 |
| Non‑Equity Incentive Plan Compensation | 213,312 | 112,160 | 217,346 |
| All Other Compensation | 452 | 619 | 650 |
| Total Compensation | 5,452,914 | 4,843,271 | 5,051,696 |
FY2025 fixed and annual bonus details:
| Item | Value |
|---|---|
| Base salary | $382,500 |
| Target bonus % | 55% of base salary (unchanged vs. FY2024) |
| Target bonus ($) | $210,375 |
| Actual incentive payout | $220,789 (50% cash, 50% fully‑vested RSUs) |
Performance Compensation
FY2025 Executive Bonus Plan outcomes:
| Metric | Weight | Target | Result | Achievement | Payout % | Weighted contribution |
|---|---|---|---|---|---|---|
| Revenue (USD mm) | 50% | $1,082.50 | $1,090.13 | 100.70% | 102.11% | 51.06% |
| Non‑GAAP Operating Income (USD mm) | 50% | $292.28 | $303.65 | 103.89% | 107.78% | 53.89% |
| Total payout | — | — | — | — | — | 104.95% |
FY2025 equity awards (Dylan Smith):
| Grant date | Award type | Shares/Target | Key performance metric(s) | Actual earned | Vesting schedule |
|---|---|---|---|---|---|
| 2024‑04‑03 | RSUs | 80,000 | — | — | 1/16 on 2024‑06‑20, then quarterly thereafter, subject to service |
| 2024‑04‑03 | PSUs | 80,000 target | FY2025 Revenue (50%); FY2025 Non‑GAAP Op Inc (50%) | 85,304 earned (106.63% of target) | 1/3 on 2025‑04‑02; 1/3 on 2026‑04‑02; 1/3 on 2027‑04‑02, subject to service |
Outstanding stock options (as of 2025‑01‑31):
| Grant date | Exercisable | Exercise price | Expiration |
|---|---|---|---|
| 2015‑06‑18 | 34,000 | $17.52 | 2025‑06‑18 |
| 2017‑04‑09 | 450,000 | $16.68 | 2027‑04‑09 |
| 2019‑04‑03 | 300,000 | $20.12 | 2029‑04‑03 |
| Approx. in‑the‑money value at $33.39 close (2025‑01‑31) | — | — | ~$12.0M (34,000×(33.39–17.52) + 450,000×(33.39–16.68) + 300,000×(33.39–20.12)) using $33.39 close |
Additional realized activity (FY2025): 260,000 options exercised ($3,602,600 value realized) and 169,055 stock awards vested ($4,913,140 value realized) .
Equity Ownership & Alignment
| Item | Detail |
|---|---|
| Beneficial ownership (Class A) | 2,047,136 shares; 1.4% of Class A outstanding |
| Breakdown within 60 days of 2025‑04‑16 | 784,000 options exercisable; 3,571 RSUs vesting within 60 days |
| Stock ownership guideline | 2× base salary for NEOs other than CEO |
| Compliance status | NEOs met, exceeded, or on track as of 2025‑04‑16 |
| Hedging/pledging | Prohibited for officers; no pledging allowed |
| 10b5‑1 plan | Active 10b5‑1 trading plan in place for Dylan Smith as of proxy date |
| Clawback policy | NYSE‑compliant clawback adopted Sep 2023; applies to Section 16 officers |
Selected unvested positions at FY2025 year‑end (market value at $33.39 close):
- RSUs across multiple grants remained unvested; per‑grant counts and market values disclosed (e.g., 65,000 RSUs at $2,170,350) .
- PSUs granted in FY2025 were initially shown as 80,000 target with $2,671,200 notional; subsequently determined at 85,304 earned and subject to time‑based vesting (1/3 per year starting 2025‑04‑02) .
Employment Terms
Change‑in‑control and severance protections (double‑trigger CIC, “change in control period” = 3 months before to 12 months after a CIC) :
- Involuntary termination without cause outside CIC period: lump sum 6 months base salary and 6 months paid COBRA (base salary $382,500) .
- Involuntary termination without cause or resignation for good reason during CIC period: lump sum 12 months base salary, 100% target bonus (target $210,375), 12 months paid COBRA, and 100% acceleration of unvested equity .
- 280G “best‑net” cutback (no tax gross‑ups) .
Investment Implications
- Alignment and governance: Large in‑the‑money option position and multi‑year PSUs/RSUs concentrate Smith’s upside on operating execution and TSR; prohibitions on hedging/pledging, robust clawback, and ownership guidelines strengthen alignment .
- Pay‑for‑performance momentum: FY2025 bonus paid at 104.95% of target on revenue and non‑GAAP operating income beats; FY2025 PSUs for NEOs (incl. Smith) earned at 106.63% of target, indicating attainable but demanding targets tied to growth and profitability .
- Vesting and potential selling pressure: Quarterly RSU vesting plus PSU installments on 2026‑04‑02 and 2027‑04‑02, alongside expiring deep ITM options (2025/2027/2029), can create periodic liquidity events; Smith exercised 260,000 options in FY2025 and operates under an active 10b5‑1 plan, which may smooth transactions over time .
- Retention under strategic scenarios: Double‑trigger CIC terms (cash + 100% target bonus + full equity acceleration) provide retention during M&A processes while mitigating abrupt talent loss; the magnitude of accelerated equity underscores the importance of continuity in a transaction .