Jonathan Vassil
ToastAbout Jonathan Vassil
Jonathan Vassil is Chief Revenue Officer (CRO) of Toast, serving in the role since January 2022 after leading Toast’s Sales and Onboarding organizations from August 2017 to January 2022. He is 48, holds a B.S. in Behavioral Sciences from the University of Maryland and an MBA from the University of Virginia’s Darden School of Business, and brings deep experience in SMB sales, operations, and marketplace development . Toast’s 2024 performance context included 34% year-over-year growth in non-GAAP subscription and financial technology solutions gross profit (RGP) to $1,417M, GAAP net income of $19M (first-time profitability), and Adjusted EBITDA of $373M, alongside record net adds of 28,000 locations to ~134,000 total—key metrics used to fund executive bonuses tied to RGP and Adjusted EBITDA .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Toast, Inc. | Chief Revenue Officer | Jan 2022–present | Leads revenue organization; background in SMB sales/operations/marketplace development |
| Toast, Inc. | Head of Sales & Onboarding | Aug 2017–Jan 2022 | Led customer acquisition and onboarding functions |
| GolfNow (Comcast) | Senior leadership roles | Not disclosed | Growth and marketplace development experience |
| OrderUp | Senior leadership roles | Not disclosed | SMB sales/operations expertise |
| Groupon, Inc. | Senior leadership roles | Not disclosed | SMB sales/operations expertise |
External Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Several early-stage startup companies | Board member | Not disclosed | Board service at early-stage startups |
Fixed Compensation
| Year | Base Salary ($) | Target Bonus % | Target Bonus ($) | Actual Bonus Paid ($) | Notes |
|---|---|---|---|---|---|
| 2024 | 391,221 | 100% | 391,221 | 521,420 | Base increased from $380,500 to $394,769 on Apr 1, 2024 |
Performance Compensation
Annual STI Bonus Mechanics (2024)
| Metric | Weighting | Target | Actual | Funding Contribution |
|---|---|---|---|---|
| RGP | 70% | 100% funding at target | Between target and maximum; 140% achievement | 98% |
| Adjusted EBITDA | 30% | 100% funding at target | Target exceeded; 125% achievement | 38% |
| Total Funding | 100% | — | — | 136% |
| Individual MBO Multiplier (Vassil) | — | — | 98% | Final payout = 136% × 98% = $521,420 |
Toast does not disclose specific numeric targets for RGP and Adjusted EBITDA due to competitive sensitivity; targets are set at rigorous, objective levels .
Annual LTI Awards (2024 grants approved)
| Component | Grant Date | Shares/Options (#) | Exercise Price ($/sh) | Grant Date Fair Value ($) | Vesting | Expiration |
|---|---|---|---|---|---|---|
| Stock Options | 3/11/2024 | 146,602 | 24.65 | 2,137,501 | Vests in 16 equal quarterly installments over 4 years from 4/1/2024 | 3/11/2034 |
| RSUs | 3/11/2024 | 79,783 | — | 1,966,651 | Vests in 16 equal quarterly installments over 4 years from 4/1/2024 | — |
Toast’s 2024 LTI mix for executives was 60% options and 40% RSUs; Vassil’s approved grant value was $3,562,500 (options $2,137,500; RSUs $1,425,000). Options have a 10-year term and are granted at the closing price on grant date .
Equity Ownership & Alignment
Beneficial Ownership (as of Mar 31, 2025)
| Category | Amount | % of Shares Outstanding | Notes |
|---|---|---|---|
| Total Beneficial Ownership (Class A) | 1,073,006 | <1% | — |
| Directly Held Shares (Class A) | 48,388 | — | — |
| Options Exercisable within 60 Days (Class A) | 1,011,950 | — | Immediately exercisable |
| RSUs Releasable within 60 Days (Class A) | 12,668 | — | — |
Outstanding Equity Awards (Year-End 2024)
| Grant Date | Type | Exercisable (#) | Unexercisable (#) | Exercise Price ($) | Expiration | Unvested RSUs (#) | RSU Market Value ($) |
|---|---|---|---|---|---|---|---|
| 6/24/2019 | Options | 198,996 | — | 2.07 | 6/24/2029 | — | — |
| 4/21/2020 | Options | 454,755 | — | 2.21 | 4/21/2030 | — | — |
| 3/15/2022 | Options | 175,517 | 79,781 | 17.38 | 3/15/2032 | 14,671 | 534,758 |
| 3/10/2023 | Options | 85,590 | 142,651 | 17.33 | 3/10/2033 | 47,479 | 1,730,610 |
| 3/11/2024 | Options | 18,325 | 128,277 | 24.65 | 3/11/2034 | 69,811 | 2,544,611 |
2024 Realized Equity Values (Liquidity pressure indicator)
| Options Exercised (#) | Value Realized on Exercise ($) | RSUs Vested (#) | Value Realized on Vesting ($) |
|---|---|---|---|
| 550,000 | 14,634,776 | 40,701 | 1,017,792 |
Alignment Policies
- Anti-hedging and anti-pledging: Hedging, pledging, and margin use of Toast shares are prohibited under the Stock Trading Policy .
- Stock ownership guidelines: Executive officers (other than CEO/founders) must reach, by Dec 31, 2027, the lesser of 15,000 shares or an amount equivalent to 2x base salary; only directly/beneficially owned and vested DSUs count .
- 10b5-1 plans: Executives are required to pre-plan stock sales via 10b5-1 plans .
- No single-trigger vesting: Equity awards only vest upon qualifying termination following a change in control when awards are assumed/continued/substituted .
Employment Terms
| Scenario | Cash Severance ($) | Health Care Benefits ($) | Equity Acceleration ($) | Notes |
|---|---|---|---|---|
| Termination without Cause or for Good Reason – Not in Connection with CIC | 785,990 | 16,437 | 6,299,612 | Per Severance Policy; CIC period is 3 months prior to and 12 months following a CIC |
| Termination without Cause or for Good Reason – In Connection with CIC | 1,570,207 | 24,655 | 12,284,558 | Double-trigger vesting applies when awards are assumed |
Additional governance:
- Clawback policy: Adopted Oct 2, 2023; recovers incentive-based compensation granted/earned/vested on financial reporting measures during the three years preceding a restatement, subject to limited exceptions .
- No 280G excise tax gross-ups; no discounting or repricing of underwater options .
Compensation Peer Group (Benchmarking)
- Peer group used for 2024 decisions (selected Aug 2023): Affirm, AppLovin, BILL, Datadog, DoorDash, Dynatrace, Etsy, HubSpot, MongoDB, Paycom, Paylocity, Procore, PTC, Shift4 Payments, Smartsheet, The Trade Desk, Twilio, Unity, ZoomInfo .
- Committee references 25th/50th/75th percentiles; does not set pay solely to a specific percentile .
- Peer group reevaluated July 2024 with no changes; used for 2025 decisions .
Investment Implications
- Pay-for-performance alignment: STI tied to RGP (70%) and Adjusted EBITDA (30%) with rigorous targets; 2024 payout at 133% of target for Vassil after 136% funding and 98% MBO multiplier—direct linkage to profitable growth and efficiency .
- Retention vs dilution: 2024 LTI mix remains performance-levered (60% options, 40% RSUs) with quarterly vesting over four years, balancing retention and shareholder alignment; options only deliver value above $24.65 strike .
- Selling pressure watch: 2024 exercises of 550,000 options (value realized ~$14.6M) and RSU vesting indicate material realized liquidity; however, 10b5-1 plan requirements and anti-pledging/hedging policies mitigate opportunistic or misaligned trading risk .
- Change-of-control economics: Double-trigger design and substantial equity acceleration in CIC ($12.3M) imply meaningful retention/transition compensation but avoid single-trigger acceleration and 280G gross-ups—generally shareholder-friendly governance .
- Ownership alignment: Beneficial ownership includes significant immediately exercisable options and 48,388 directly held shares; stock ownership guidelines enforce a minimum ownership ramp by 2027 to strengthen alignment .