David Obstler
DatadogAbout David Obstler
David Obstler is Chief Financial Officer of Datadog (since November 2018) with 30+ years across software, fintech, and capital markets. He holds an MBA from Harvard Business School and a BA from Yale University . As CFO in 2024, Datadog delivered revenue of $2.68B (+26% y/y) with 25% non-GAAP operating margin, while GAAP EPS was $0.52; TSR (value of $100) ended 2024 at $378 vs $321 in 2023, reflecting strong multi-year execution despite 2022 volatility . His pay-for-performance is tied to net new ARR (annual cash bonus) and annual revenue with a non-GAAP operating income gate (PSUs), aligning incentives to growth and profitability .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Braze, Inc. | Director | May 2021–Present | Public software board experience; cross-pollination in scaled SaaS go-to-market and finance |
| TravelClick, Inc. | Chief Financial Officer | Sep 2014–Oct 2018 | Led finance at hospitality tech through scale-up and sale phase |
| OpenLink Financial LLC | Chief Financial Officer | Nov 2012–Jul 2014 | Drove financial operations at financial services software provider |
| MSCI Inc. | Chief Financial Officer | Jun 2010–Sep 2012 | Public company CFO; index/data and investment software |
| Risk Metrics Group, Inc. | Chief Financial Officer | Jan 2005–Jun 2010 | CFO through growth in risk/ESG governance services |
| J.P. Morgan; Lehman Brothers; Goldman Sachs | Investment Banking roles | Earlier career | Capital markets, advisory foundation for operating CFO roles |
External Roles
| Organization | Role | Years | Notes |
|---|---|---|---|
| Braze, Inc. | Director | May 2021–Present | Public company board; committees not specified here |
Fixed Compensation
| Metric | 2022 | 2023 | 2024 |
|---|---|---|---|
| Base Salary ($) | 395,833 | 400,000 | 420,833 (annual rate raised to $425,000 effective Mar 1, 2024) |
| Target Bonus ($) | — | 375,000 | 400,000 |
| Actual Bonus Paid ($) | 306,873 | 335,546 | 371,295 |
| Bonus Payout (% of Target) | — | 89% | 93% |
Notes:
- 2024 target bonus set at 94% of base salary ($400,000) with 200% cap; payout driven by net new ARR with decelerators if non-GAAP operating income missed .
- 2024 bonus funded at ~93% on 93% net new ARR target attainment and meeting the non-GAAP operating income target .
Performance Compensation
Annual Cash Bonus Plan (Company-wide CFO plan)
| Item | 2023 | 2024 |
|---|---|---|
| Metric | Net new ARR; decelerators if non-GAAP operating income below target | Net new ARR; decelerators if non-GAAP operating income below target |
| Achievement vs Target | ~89% net new ARR; non-GAAP operating income target achieved | ~93% net new ARR; non-GAAP operating income target achieved |
| Payout vs Target | 89% | 93% |
| Bonus ($) | $335,546 | $371,295 |
Long-term Equity (PSUs/RSUs; 50%/50% target mix)
| Item | 2023 Grants/Results | 2024 Grants/Results |
|---|---|---|
| Target PSUs Granted (#) | 65,255 (granted 4/25/2023) | 60,582 (granted 5/29/2024) |
| Target RSUs Granted (#) | 65,255 (granted 4/25/2023) | 60,582 (granted 5/29/2024) |
| PSU Performance Metric | Annual revenue with non-GAAP operating income gate; 92–200% payout curve | Annual revenue with non-GAAP operating income gate; 88–200% payout curve |
| Revenue Achievement | 99% of target; gate achieved | 100.5% of target; gate achieved |
| PSU Payout (% Target) | 92% | 115% |
| PSUs Earned (#) | 60,189 | 69,859 |
| Grant-Date Fair Value ($) | $8,181,672 total (PSUs+RSUs) | $14,743,236 total (PSUs+RSUs) |
Vesting Schedules (Service-based after performance certification for PSUs)
| Award Year | Instrument | Initial Vest Date | Cadence |
|---|---|---|---|
| 2023 | RSUs | Mar 1, 2024 | 25% at initial date; then 12 equal quarterly installments each Jun 1, Sep 1, Dec 1, Mar 1 |
| 2023 | Earned PSUs (92%) | Mar 1, 2024 | 25% at initial date; then 12 equal quarterly installments each Jun 1, Sep 1, Dec 1, Mar 1 |
| 2024 | RSUs | Mar 1, 2025 | 25% at initial date; then 12 equal quarterly installments each Jun 1, Sep 1, Dec 1, Mar 1 |
| 2024 | Earned PSUs (115%) | Mar 1, 2025 | 25% at initial date; then 12 equal quarterly installments each Jun 1, Sep 1, Dec 1, Mar 1 |
Equity Ownership & Alignment
Beneficial Ownership (as of March 15, 2025)
| Component | Shares |
|---|---|
| Class A common (direct) | 159,550 |
| Class B common (direct) | 15,603 |
| Class B common (Obstler Children 2019 Trust) | 92,397 |
| Options exercisable within 60 days (Class B) | 107,500 |
| Ownership as % of total voting power | <1% (denoted “*” in company table) |
Policy alignment:
- Company prohibits hedging, short sales, purchasing on margin, and pledging of company stock; covers directors, officers, employees .
- Clawback policy compliant with SEC/Nasdaq rules: recoup erroneously-awarded incentive compensation after an accounting restatement over prior 3 fiscal years .
Outstanding Equity Awards (Unvested) at Dec 31, 2024
| Award Type | Shares Unvested |
|---|---|
| RSUs (2021 grant) | 4,996 |
| PSUs earned prior (2022 cycle; service vesting ongoing) | 17,360 |
| RSUs (2022 grant) | 14,405 |
| PSUs earned (2023 cycle; service vesting ongoing) | 33,855 |
| RSUs (2023 grant) | 36,708 |
| PSUs earned (2024 cycle; certified Feb 25, 2025; service vesting begins Mar 1, 2025) | 69,859 |
| RSUs (2024 grant) | 60,582 |
| Stock Options (exercisable) | 107,500 at $1.55 strike, exp. 9/5/2028 |
Insider Selling and Vesting Flow (Liquidity Indicators)
| Metric | 2023 | 2024 |
|---|---|---|
| Options exercised (#) | 250,000 | 200,000 |
| Value realized on option exercise ($) | 24,664,382 | 24,970,631 |
| Shares vested (RSU/PSU) (#) | 120,130 | 114,917 |
| Value realized on vesting ($) | 11,263,840 | 14,744,463 |
Interpretation:
- Quarterly vest dates (Mar 1, Jun 1, Sep 1, Dec 1) and material unvested PSU/RSU balances suggest recurring scheduled supply; policy prohibits hedging/pledging which mitigates leverage risk .
Employment Terms
| Scenario | Cash Severance | Bonus | COBRA | Equity |
|---|---|---|---|---|
| Termination without Cause or for Good Reason | Lump sum equal to 6 months base salary | 50% of annual target bonus | 6 months | No acceleration (performance awards follow plan terms) |
| CIC + (Termination without Cause or for Good Reason within 3 months prior / 12 months after CIC) | Lump sum equal to 12 months base salary | 100% of annual target bonus | 12 months | 100% vesting of outstanding unvested equity, excluding performance-based awards unless already earned/certified; earned PSUs then follow time-based acceleration |
Mr. Obstler’s offer letter includes an alternative severance if more favorable: 6 months salary paid on payroll, prorated target bonus for greater of time employed or 6 months (paid pro rata over six months), and up to 6 months COBRA, contingent on a release .
Indicative CIC economics as of 12/31/2024:
- If terminated in connection with a CIC: base $425,000; bonus $400,000; accelerated equity $23,992,088; COBRA $29,965; total ~$24,847,053 .
Performance & Track Record (Company-level under CFO tenure)
Revenue and Margin
| Metric | 2023 | 2024 |
|---|---|---|
| Revenue ($B) | 2.13 | 2.68 |
| Non-GAAP Operating Margin (%) | 23% | 25% |
Total Shareholder Return (Value of $100 at year-end)
| Year | 2020 | 2021 | 2022 | 2023 | 2024 |
|---|---|---|---|---|---|
| DDOG TSR ($) | 261 | 471 | 195 | 321 | 378 |
Other governance and compensation program signals:
- Say-on-Pay approval: ~96% in 2023 cycle; ~95% in 2024 cycle, indicating strong shareholder support for NEO pay design .
- Peer benchmarking uses high-growth SaaS/security peers (e.g., CrowdStrike, Snowflake, Zscaler, Fortinet, HubSpot, MongoDB, Cloudflare, etc.), with Compensia advising .
Compensation Structure Analysis (Signals)
- Mix: Heavy equity (50% PSUs / 50% RSUs) with one-year performance measurement and four-year service vesting; annual cash bonuses tied to net new ARR with profitability guardrails .
- Metric stringency: PSU revenue targets set at ambitious growth rates (e.g., 26% y/y in 2024); resulted in 115% payout on 100.5% achievement in 2024; 92% payout in 2023 on 99% achievement .
- No hedging/pledging; clawback in place; no excise tax gross-ups; double-trigger CIC only—generally shareholder-friendly constructs .
- Cash/equity trend: Base increased to $425k in 2024; target bonus raised to $400k (94% of base) to align with peers; equity grant value increased y/y reflecting role scope and market benchmarks .
Investment Implications
- Alignment: Obstler’s incentives are tightly linked to growth (net new ARR; annual revenue PSU metric) and profitability (non-GAAP operating income gate), supporting balanced growth and margin expansion; strong say-on-pay support de-risks pay protests .
- Supply/vesting overhang: Material unvested RSU/PSU balances and quarterly vest cadence may create predictable selling pressure around Mar/Jun/Sep/Dec, compounded by ongoing option exercises (200–250k annually in 2023–24); monitor Form 4s into vest windows .
- Retention/CIC risk: Severance is moderate (6 months base + 50% target bonus), with double-trigger CIC equity acceleration only for earned awards—adequate retention without excessive change-in-control payouts; CIC economics ~ $24.8M as of YE24 are mostly equity-driven, aligning with shareholder interests .
- Skin-in-the-game: Beneficial ownership includes Class A/B and options but totals <1% voting power; alignment is chiefly via unvested PSUs/RSUs rather than large outright holdings; pledging/hedging bans reduce misalignment risk .
- Execution track: Under Obstler in 2024, DDOG grew revenue 26% with 25% non-GAAP operating margin; TSR improved to $378 (from $321 in 2023), indicating investor confidence as growth re-accelerated with margin discipline .