Timothy Regan
DROPBOXAbout Timothy Regan
Timothy Regan, CPA, is Dropbox’s Chief Financial Officer (age 48). He has served as CFO since September 2020, after joining Dropbox in 2016 as Chief Accounting Officer; prior roles include VP Finance Controller at Pandora (2011–2016), and senior positions at Dolby Laboratories and Ernst & Young. He holds a B.A. in Accounting from Georgetown (1999) and an MBA from UC Berkeley Haas (2011) . In 2024, Dropbox’s annual bonus plan recognized FX-neutral revenue of $2,545M (99% of target) and non-GAAP operating margin of 36.1% (above target), though management capped corporate funding at 100%; over the last five years, cumulative TSR rose ~68% versus 201% for the Nasdaq Computer Index peer benchmark .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Dropbox, Inc. | Chief Financial Officer | Sep 2020–present | Company-wide finance leadership; public-company CFO responsibilities |
| Dropbox, Inc. | Chief Accounting Officer | Dec 2016–Sep 2020 | Built controllership, financial reporting, and accounting operations |
| Pandora Media, Inc. | VP Finance Controller | 2011–2016 | Finance controllership for a scaled consumer tech platform |
| Dolby Laboratories; Ernst & Young | Senior finance roles | Not disclosed | Accounting/audit and finance leadership experience |
External Roles
| Organization | Role | Years | Notes |
|---|---|---|---|
| — | — | — | No public company board roles disclosed for Mr. Regan in the 2025 proxy . |
Fixed Compensation
| Metric | 2022 | 2023 | 2024 |
|---|---|---|---|
| Base Salary ($) | 518,333 | 560,000 | 560,000 |
| Target Bonus (% of Salary) | Not disclosed | Not disclosed | 85% (Target $476,000) |
| Actual Bonus Paid ($) | 270,000 | 348,000 | 623,000 |
Notes:
- CEO base salary changes are disclosed for context; Mr. Regan’s did not change in 2024 .
- Target bonus percentages for 2022–2023 are not specified; 2024 target for CFO is 85% of salary .
Performance Compensation
Annual cash incentive (2024) – Plan design and outcomes:
- Corporate metrics and weights: Revenue (67%) and Non-GAAP Operating Margin (33%) .
- Targets: Revenue $2,565M (threshold $2,488M; max $2,642M); Non-GAAP Op Margin 33.1% (threshold 29.8%; max 36.4%) .
- Results used for funding: Revenue $2,545M (99% of target); Non-GAAP Op Margin 36.1% (>target). Corporate funding was discretionarily capped at 100% due to cost savings from the October 2024 workforce reduction .
- Individual results: Mr. Regan’s bonus paid was 131% of his target, indicating a positive individual performance multiplier on top of the 100% corporate funding outcome .
| Metric | Weight | Threshold | Target | Maximum | Actual 2024 | Corporate Funding Applied |
|---|---|---|---|---|---|---|
| Revenue (FX-neutral, $M) | 67% | 2,488 | 2,565 | 2,642 | 2,545 | 100% (capped) |
| Non-GAAP Operating Margin | 33% | 29.8% | 33.1% | 36.4% | 36.1% | 100% (capped) |
| CFO Bonus Outcome | — | — | $476,000 target | — | $623,000 paid | 131% of target |
Equity awards (time-based RSUs; no options in 2024):
- 2024 grant: 207,180 RSUs (grant date 4/1/2024); grant-date fair value $5,034,474; vesting in equal quarterly installments over 4 years; as of 12/31/2024, 168,334 RSUs remained unvested from this grant (reflecting three quarterly vests during 2024) .
- Company does not grant stock options to NEOs (and has never granted SARs); equity mix emphasizes RSUs .
| Grant | Grant Date | RSUs Granted | Unvested at 12/31/2024 | Vesting Schedule | Grant-Date Fair Value ($) |
|---|---|---|---|---|---|
| CFO Annual RSU | 4/1/2024 | 207,180 | 168,334 | Equal quarterly over 4 years | 5,034,474 |
| Prior RSU (2023) | 4/1/2023 | — | 123,875 | Equal quarterly over 4 years | — |
| Prior RSU (2022) | 4/1/2022 | — | 63,074 | Equal quarterly over 4 years | — |
| Prior RSU (2021) | 4/1/2021 | — | 10,950 | Equal quarterly over 4 years | — |
Realized vesting in 2024:
- Shares acquired on vesting: 229,480; value realized: $6,045,762 (all stock awards) .
Equity Ownership & Alignment
Ownership, guidelines, and policies:
- Beneficial ownership: 102,295 Class A shares; <1% of outstanding; no Class B holdings .
- Ownership guidelines: Executives must own 2x base salary in stock or equivalents; all NEOs have met, exceeded, or are on track to meet guidelines within five years of December 1, 2023 or appointment date .
- Hedging/pledging: Prohibited for employees, officers, and directors .
- Clawback: Nasdaq-compliant policy adopted in August 2023 covering incentive-based compensation tied to financial reporting measures upon an accounting restatement .
Unvested vs. vested equity at 12/31/2024 (CFO):
| Category | Shares/Units | Market/Value Basis |
|---|---|---|
| Unvested RSUs (all grants) | 366,233 (10,950 + 63,074 + 123,875 + 168,334) | $11,001,639 total market value, at $30.04/share |
| Options (Exercisable/Unexercisable) | 0 / 0 | No options disclosed |
| Shares vested in 2024 | 229,480 | Value realized: $6,045,762 |
Employment Terms
At-will employment and restrictive covenants:
- Executives are at-will; agreements include covenants prohibiting competition during employment, non-solicitation post-employment, and confidentiality protocols; specific durations not disclosed in proxy .
Severance protections:
- Outside Change-in-Control (CIC): 0.5x annual base salary; up to 6 months COBRA; for Mr. Regan, 3 months’ accelerated vesting of unvested time-based RSUs (subject to release and other conditions) .
- CIC (double-trigger within 3 months before or 12 months after CIC): 1.0x base salary; 1.0x target annual bonus; up to 12 months COBRA; 100% acceleration of all outstanding equity awards (performance awards deemed at target unless otherwise specified), subject to release and other conditions . No excise tax gross-ups; “better-after-tax” cutback applies if 280G would otherwise apply .
Potential payments (as of 12/31/2024 valuation):
| Scenario | Base Salary ($) | Target Bonus ($) | Equity Acceleration ($) | Benefits ($) | Total ($) |
|---|---|---|---|---|---|
| Involuntary termination (outside CIC) | 280,000 | — | 1,510,351 | 15,777 | 1,806,128 |
| Qualifying termination (within CIC period) | 560,000 | 476,000 | 11,001,639 | 31,553 | 12,069,193 |
Other practices:
- No guaranteed bonuses; no executive retirement plans or non-qualified deferred comp for executives; no tax gross-ups on perquisites or excise tax gross-ups in CIC; perquisites are limited (security program disclosed only for CEO) .
Performance & Track Record
Business trends (company-level):
| KPI | 2023 | 2024 |
|---|---|---|
| Revenue ($M) | 2,548.2 | 2,501.6 |
| Paying Users (M) | 18.12 | 18.22 |
| ARPU ($) | 140.23 | 139.38 |
| Non-GAAP Operating Margin (%) | 36.4% | 32.8% |
| Free Cash Flow ($M) | 871.6 | 759.4 |
Plan performance (for 2024 bonus funding calculations):
- FX-neutral annual revenue: $2,545M (99% of $2,565M target) .
- Non-GAAP operating margin: 36.1% (above 33.1% target); corporate funding cap applied at 100% .
Capital markets performance and shareholder feedback:
- Five-year cumulative TSR: Company +68% (ending value $167.73 on $100 initial) vs Nasdaq Computer Index +201% (ending value $301.44) .
- Say-on-Pay approval in 2024 proxy cycle: 98.3% support, signaling strong shareholder endorsement of executive pay practices .
Compensation Committee, Peer Group, and Benchmarking
- Compensation philosophy emphasizes pay-for-performance with a significant RSU component; no stock options granted to NEOs in 2024; clawback and robust ownership guidelines in place .
- 2024 peer group (used as a market reference, not strict benchmarking) included: Affirm, AppLovin, Box, DocuSign, Dolby, Elastic, Etsy, F5, GoDaddy, HubSpot, Informatica, Nutanix, Okta, Paycom, Pinterest, Pure Storage, RingCentral, Roku, Splunk, Teradata, Zoom Communications; updates added Elastic, Informatica, Zoom and removed Citrix and Zendesk .
- Target percentile for pay positioning is not specified; committee uses peer data as a guide alongside company performance and role scope .
Equity Ownership & Alignment Details (Supplemental)
| Item | Status |
|---|---|
| Beneficial ownership (CFO) | 102,295 Class A shares; <1%; no Class B |
| Ownership guidelines | Executives: 2x salary; on track or met for all NEOs |
| Hedging/Pledging | Prohibited |
| Clawback | Nasdaq-compliant policy adopted Aug 2023 |
Investment Implications
- Incentive alignment: CFO’s 2024 bonus tied to revenue (67%) and non-GAAP operating margin (33%), with 131% payout of target; quarterly-vesting RSUs dominate long-term compensation, aligning realized value with stock performance and creating ongoing retention via unvested awards ($11.0M unvested value at YE’24) .
- Retention and change-in-control: Modest baseline severance (0.5x salary) but strong double-trigger CIC protection (1x salary + 1x target bonus + 100% equity acceleration) reduces departure risk through a sale and aligns incentives during strategic transactions .
- Governance safeguards: Prohibitions on hedging/pledging, robust ownership guidelines, and a clawback policy mitigate misalignment and reputational risks; Say-on-Pay support (98.3%) indicates shareholder approval of pay design .
- Operating levers: 2024 FX-neutral revenue achievement (99% of target) and above-target non-GAAP margin (capped for funding) reflect disciplined cost management; however, year-over-year headwinds included lower reported revenue, ARPU, margin, and free cash flow, and multi-year TSR underperformance relative to the Nasdaq Computer Index, underscoring execution risk on growth and monetization initiatives .