Matthew Calkins
APPIANAbout Matthew Calkins
Matthew Calkins, 52, is Appian’s Founder, Chief Executive Officer, President, and Chairman of the Board, roles he has held since August 1999; he previously served as a director of MicroStrategy from November 2004 to April 2014 and holds a B.A. in Economics from Dartmouth College . Appian’s FY2024 results under his leadership show subscriptions revenue up 19% to $490.6M, total revenue $617.0M, with adjusted EBITDA turning positive to $20.3M from a $(44.8)M loss in FY2023 and GAAP net loss improving to $(92.3)M from $(111.4)M . Over 2020–2024, the pay-versus-performance table reports the value of a fixed $100 investment in APPN at $424.21 (2020), $170.66 (2021), $85.21 (2022), $98.56 (2023), and $86.31 (2024), alongside net losses each year, indicating volatile TSR and improving operating profile in 2024 .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Appian | CEO, President, Chairman | Since Aug 1999 | Founder-led execution; dual role centralizes strategy and oversight |
| Appian | Founder | Since 1999 | Long-term product vision; process-focused platform growth |
External Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| MicroStrategy, Inc. | Director | Nov 2004–Apr 2014 | Public board experience; enterprise software governance expertise |
Fixed Compensation
| Metric | FY 2022 | FY 2023 | FY 2024 |
|---|---|---|---|
| Base Salary ($) | $915,625 | $1,000,000 | $1,000,000 |
| Bonus/Retention ($) | — | — | — |
| Non-Equity Incentive Paid ($) | $99,000 | $150,000 | $150,000 |
| Option/Stock Awards Grant-Date Fair Value ($) | $18,823,638 (options) | — | — |
| All Other Compensation ($) | $12,380 | $13,566 | $276 |
| Total Compensation ($) | $19,850,643 | $1,163,566 | $1,150,276 |
Performance Compensation
| Instrument/Plan | Metric | Weighting | Target | Actual/Payout | Vesting Terms |
|---|---|---|---|---|---|
| Senior Executive Cash Incentive Bonus Plan (FY2024) | Total software ACV growth; executive alignment with corporate strategy | Not disclosed | Not disclosed | $150,000 for Calkins; discretionary by executive committee | Cash bonus paid post-year; no vesting schedule |
| 2022 CEO Option Grant | Stock price thresholds ($175, $200, $225, $250 average closing price over 365 days) | N/A (price-trigger) | Thresholds as specified | Not disclosed whether thresholds met; unexercisable 700,000 options as of 12/31/2024 | Vests 25% at each threshold before June 7, 2030; option expires June 7, 2032; exercise price $50.63 |
| Insider Trading Policy | Hedging/short sales banned; pledging not prohibited | N/A | N/A | N/A | N/A |
Equity Ownership & Alignment
| Category | Detail | Amount | Notes |
|---|---|---|---|
| Total Beneficial Ownership | Shares | 28,994,207 | 39.1% of shares outstanding assuming Class B conversion |
| Voting Control | Status | Controls >50% of voting power | Controlled company under Nasdaq rules |
| Breakdown – Direct | Class A common | 1,778,327 | Directly held |
| Breakdown – Wallingford, LLC | Class B common | 6,941,070 | Managing member |
| Breakdown – Calkins Family LLC | Class B common | 20,274,710 | Managing member |
| Options – 2017 grant | Exercisable | 100 at $12.00, exp. 4/25/2027 | Legacy options |
| Options – 2022 grant | Unexercisable | 700,000 at $50.63, exp. 6/7/2032 | Price-threshold vesting |
| Shares Pledged (RED FLAG) | Pledged collateral | 1,778,327 Class A (direct); 2,883,333 Class B (Wallingford); 1,600,000 Class B (Calkins Family LLC) | Pledging permitted under policy; increases forced-sale risk |
| Ownership Guidelines | Requirement | No executive ownership requirements; pledging not prohibited | Alignment relies on large founder stake |
| 2024 Exercises | Options exercised | 1,444,183 shares; value realized $33,866,092 | Indicates significant exercise activity in 2024 |
Employment Terms
| Term | CEO Provision | Notes |
|---|---|---|
| Employment Agreement | Standard at-will; non-compete/confidentiality/IP | No severance or change-in-control payments for CEO |
| Change-in-Control (CIC) | No automatic vesting under plans; no single-trigger CIC payments | Equity plan forfeiture applies to unvested RSUs on termination |
| Clawback | Executive incentive comp recoupment upon restatement (3-year lookback) | Nasdaq Rule 10D-1 compliant |
| Tax Gross-ups | No Section 280G gross-ups | Shareholder-friendly feature |
Board Governance
- Structure: CEO serves as Chairman; company cites unified leadership benefits; four of nine directors are independent; Appian qualifies as a “controlled company” due to Calkins’ voting control .
- Board activity: Met four times in 2024; each director attended ≥75% of meetings; six of seven directors attended the 2024 annual meeting .
- Committees:
- Audit (Chair: Shirley Edwards; members: Edwards, Kilberg, Biddle; all independent; Edwards is an “audit committee financial expert”) .
- Compensation (Chair: Kilberg; members: Kilberg, Hartman, McCarthy; McCarthy not independent due to prior compensated roles) .
- Nominating & Governance (Chair: Kilberg; members: Kilberg, McCarthy; Kilberg independent) .
Director Compensation (Context for dual-role implications)
| Item | Amount/Structure | FY2024 Detail |
|---|---|---|
| Annual non-employee director retainer | $250,000 (50% cash, 50% fully-vested stock; paid quarterly) | Example payouts: $125,071 cash + $124,929 stock for full-year directors |
| CEO/Executive Directors | No additional director pay for Calkins/Kramer | Dual-role reduces incremental cash to insiders; governance trade-offs remain |
Say-on-Pay & Compensation Committee Practices
- 2024 say-on-pay approval >95% of votes cast, signaling broad investor support for NEO compensation .
- Committee does not use a peer group; CEO advises on other NEOs but not his own pay; significant discretion in bonuses and equity grant timing .
Performance & Track Record
| Indicator | FY2020 | FY2021 | FY2022 | FY2023 | FY2024 |
|---|---|---|---|---|---|
| Value of $100 investment (APPN) | $424.21 | $170.66 | $85.21 | $98.56 | $86.31 |
| Net Income ($) | $(33,476,840) | $(88,640,479) | $(150,920,305) | $(111,440,577) | $(92,262,091) |
| Adjusted EBITDA ($) | — | — | — | $(44,840,000) | $20,257,000 |
| FY2024 business highlights | Subscriptions revenue $490.6M (+19% YoY); total revenue $617.0M; cloud subscription retention 116% | — |
Compensation Structure Analysis
- Shift in mix: No CEO equity grants in 2023–2024; large performance stock option awarded in 2022 with multi-threshold price vesting, emphasizing long-term stock price outcomes over annual RSUs .
- At-risk pay: CEO cash bonus modest at $150,000 in 2023 and 2024, determined on discretion tied to ACV growth and strategic alignment; lack of disclosed quantitative targets/weights reduces pay-for-performance transparency .
- Governance features: No option repricing; no single-trigger CIC; clawback policy in place; no ownership requirements and pledging allowed, diluting alignment safeguards .
Risk Indicators & Red Flags
- Pledging: Significant pledged share collateral by Calkins and affiliated entities (Class A and Class B), creating potential forced-sale risk in adverse market conditions .
- Controlled company with CEO as Chairman: Reduced independence requirements can heighten governance risk; four of nine directors are independent .
- Discretionary bonuses: Bonus payouts determined by executive committee without disclosed quantitative targets/weights .
- Insider activity: 2024 option exercises totaled 1,444,183 shares with $33.9M value realized; may imply liquidity needs or portfolio rebalancing, though the proxy does not state subsequent sales .
Equity Ownership & Vesting Detail (CEO Instruments)
| Instrument | Quantity | Price/Terms | Vesting/Expiration |
|---|---|---|---|
| Options (2017) | 100 | $12.00 | Exercisable; expire 4/25/2027 |
| Options (2022) | 700,000 | $50.63 | Vests 25% at each of $175/$200/$225/$250 average closing price for 365 days or qualifying corporate transaction ≥ thresholds before 6/7/2030; expire 6/7/2032 |
| Class A | 1,778,327 | N/A | Owned; pledged entirely |
| Class B (Wallingford) | 6,941,070 | 10 votes/share | 2,883,333 pledged |
| Class B (Calkins Family LLC) | 20,274,710 | 10 votes/share | 1,600,000 pledged |
Investment Implications
- Alignment vs risk: Founder’s large stake and multi-threshold price-based option grant tie long-term incentives to share price performance, but absence of ownership requirements and extensive pledging increase governance and forced-sale risks that can elevate stock volatility during drawdowns .
- Governance structure: Controlled company status and CEO/Chairman dual role reduce formal independence requirements; while board committees include independent chairs (Audit, Nominating), compensation discretion and limited disclosure on quantitative metrics lessen pay-for-performance rigor .
- Execution signals: FY2024 revenue growth and adjusted EBITDA improvement demonstrate operating momentum; if price thresholds are met, substantial option vesting could occur before 2030, potentially influencing insider exercise patterns and supply/demand dynamics around threshold proximity .
- Shareholder sentiment: >95% say-on-pay approval in 2024 suggests current compensation approach has investor support despite governance trade-offs; continued transparency on performance metrics could sustain this support .