John T. (Jack) McDonald
Upland SoftwareAbout John T. (Jack) McDonald
Founder and Chief Executive Officer of Upland since July 2010; also Chair of the Board. Age 61 as of the 2025 annual meeting; education includes B.A. in Economics from Fordham University and J.D. from Fordham Law School . Performance context: Adjusted EBITDA was $55.6M in 2024 (vs. $64.4M in 2023, $97.1M in 2022), while the value of a $100 investment in UPLD was $12.2 at YE 2024 (peer index $301.4); cumulative TSR from 12/31/2020 to 12/31/2024 was approximately -88% vs peer group +201% . Upland’s annual incentives emphasize Adjusted EBITDA and margin, and the company eliminated its M&A bonus plan in August 2024 to focus on organic growth and EBITDA .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Upland Software, Inc. | CEO; Chair | 2010–present | Founder; public SaaS operator |
| Perficient, Inc. (Nasdaq: PRFT) | CEO | 1999–2009 | Led public IT consulting firm |
| Perficient, Inc. | Chairman | 2001–2010 | Governance/oversight of public company |
| Skadden, Arps, Slate, Meagher & Flom LLP | Attorney (M&A, Corporate Finance) | 1987–1993 | Transactional expertise |
External Roles
| Organization | Role | Years | Notes |
|---|---|---|---|
| BigCommerce Holdings, Inc. (Nasdaq: BIGC) | Director; Compensation Committee member | Aug 2019–Jul 2022 | Public company board service |
| Greater Austin Chamber of Commerce | Chairman | Not specified | Civic leadership |
| Various private companies and non-profits | Director | Not specified | Broader network roles |
Fixed Compensation
| Metric | 2023 | 2024 |
|---|---|---|
| Base Salary ($) | 325,000 | 500,000 |
| Target Annual Bonus (% of Base) | 200% | 200% |
| Perquisites ($) | 15,546 | 37,330 (admin assistant and parking) |
Performance Compensation
- Annual bonus plan metrics: primary threshold Adjusted EBITDA; secondary threshold Adjusted EBITDA margin. 2024 thresholds: $55.0M EBITDA and 20.0% margin; actual: $55.6M and 20.3%; bonus pool generated $1.1M for all eligible employees .
- McDonald’s 2024 bonus outcome: Target $1,000,000; Actual $163,684 (≈16% of target) .
| 2024 Corporate Bonus Plan (Company-level) | Target | Actual |
|---|---|---|
| Adjusted EBITDA ($M) | 55.0 | 55.6 |
| Adjusted EBITDA Margin (%) | 20.0% | 20.3% |
| Bonus Pool Generated ($M) | — | 1.1 |
| 2024 Annual Bonus (McDonald) | Target ($) | Actual ($) |
|---|---|---|
| Corporate Bonus | 1,000,000 | 163,684 |
- Equity awards granted in 2024: RSUs 250,000; PSUs (target) 250,000; PSU max 750,000 .
- PSU vesting/performance: 2024 PSU vested at maximum performance with 750,000 shares acquired; value realized $3,519,063 based on closing price at vest date .
- PSU design (outstanding as of 12/31/2024): absolute TSR hurdles measured from 2/28/2023 to 12/31/2025 with payout from 0% below 5% TSR to 200% at 20% TSR; reference price $5.89; vesting upon 30-day closing price hurdles; remaining units vest based on YE price using linear interpolation .
| 2024 Equity Grants (McDonald) | Type | Target/Granted (#) | Max/Threshold (#) | Vesting |
|---|---|---|---|---|
| RSU | Granted | 250,000 | — | 12 equal quarterly installments from 3/16/2024 to 12/16/2026 |
| PSU | Target | 250,000 | Threshold 125,000; Max 750,000 | Absolute TSR hurdles; performance window 2/28/2023–12/31/2025; 30-day price hurdles; YE interpolation |
Equity Ownership & Alignment
| Ownership Detail | Amount | Notes |
|---|---|---|
| Beneficially owned common shares | 2,436,593 | 8.6% of common stock outstanding as of 4/14/2025 |
| Combined voting power | 2,436,593 | 6.8% combined voting power |
| Unvested RSUs (not included above) | 416,665 | As of record date; excluded from beneficial totals |
| Unvested PSUs (target, not included above) | 350,000 | As of record date; excluded from beneficial totals |
| Options | None | No outstanding options for NEOs in 2024 |
| Shares held via retirement custodian | 263,738 | Included in beneficial ownership |
| Trust for children | 125,000 | Not included in McDonald’s beneficial ownership; trustee Bryn Mawr Trust |
| Ownership guideline | 6× base salary (CEO) | Expected to be in compliance by end of 7-year period |
| Hedging/pledging policy | Prohibited | No short sales, margin accounts, pledging, or derivatives |
Vesting Schedules (Selected Outstanding Awards at 12/31/2024)
| Grant | Unvested Units (#) | Vesting Schedule |
|---|---|---|
| RSU grant (100,000) | 24,999 | 12 equal quarterly installments 12/16/2022–9/16/2025 |
| RSU grant (100,000) | 33,332 | 12 equal quarterly installments 3/16/2023–12/16/2025 |
| RSU grant (250,000) | 166,667 | 12 equal quarterly installments 3/16/2024–12/16/2026 |
| PSU (2013–2025 window) | 100,000 (threshold presentation) | Absolute TSR hurdles; linear interpolation at YE 2025 |
Note: Insider trading requires pre-clearance and trading blackout compliance; executives may use Rule 10b5-1 plans; hedging/pledging is prohibited, reducing leverage risk .
Employment Terms
| Term | Details |
|---|---|
| Employment agreement | Original 3/28/2017; amended 3/13/2019, 11/12/2020, 1/30/2024; at-will |
| Base salary | Increased to $500,000 on 1/30/2024 |
| Target bonus | 200% of base salary; Board approval required |
| Equity acceleration (single trigger) | If terminated without cause or resigns for good reason, all unvested equity vests in full; PSUs vest at target; service as director/consultant counts as continued service for vesting |
| Severance | Earned but unpaid bonus; 12 months base salary; 12 months COBRA reimbursement upon termination without cause or good reason |
| Double trigger CIC | Other NEOs receive double-trigger equity acceleration; McDonald already has single-trigger acceleration independent of CIC |
Estimated Potential Payments (as-of 12/31/2024 scenario)
| Scenario | Severance ($) | Equity Acceleration – with CIC ($) | Equity Acceleration – without CIC ($) | Death/Disability Equity ($) |
|---|---|---|---|---|
| Termination without cause / good reason (McDonald) | 1,526,365 | 1,410,491 | 1,410,491 | 1,410,491 |
Definitions for “Cause,” “Good Reason,” and “Change in Control” provided in proxy; include material duty reductions, salary/benefit cuts, or relocation, subject to notice and cure; CIC includes 50%+ voting power acquisition, asset sale, or board turnover, with exceptions .
Board Governance
- Roles: McDonald serves as CEO and Chair; the Board appoints a Lead Independent Director (David D. May) to provide independent oversight and preside executive sessions .
- Independence: 4 of 6 directors deemed independent (Chung, Courter, May, Walsh); Mattox not independent; CEO/Chair combined role is not independent .
- Committees: McDonald serves on no Board committees; Audit (Courter chair), Compensation (May chair), Nominating & Governance (Walsh chair) comprised of independent directors .
- Board meetings: 4 meetings in 2024; 100% attendance by all directors; all directors attended 2024 annual meeting .
- Director pay: Employee director McDonald receives no director compensation .
Compensation & Incentive Design Details
- Executive pay mix: Emphasis on at-risk compensation through RSUs/PSUs and performance-based cash; governance includes clawback policy adopted Oct 2023 compliant with SEC Rule 10D-1 and extended to 3 prior fiscal years .
- Peer group for benchmarking (2024): BIGC, CRNC, CCSI, EGIO, KLTR, LPSN, MITK, MODN, ONTF, PRCH, RMNI, SNCR, YEXT; Korn Ferry retained; NFP used earlier in 2024; no fixed percentile targeting .
- Bonus rigor: 2024 payouts under Corporate Bonus Plan were ~16% of target for participating NEOs; CRO/CSO commissions varied by quota attainment (caps at 125%) .
Performance & Track Record
| Metric | 2022 | 2023 | 2024 |
|---|---|---|---|
| Adjusted EBITDA ($M) | 97.1 | 64.4 | 55.6 |
| Net Loss ($M) | (68.4) | (179.9) | (112.7) |
| Value of $100 Investment (TSR) | 20.0 | 11.9 | 12.2 |
- Strategic shift: Elimination of M&A bonus plan (Aug 23, 2024) to focus on organic growth and Adjusted EBITDA .
- 2024 equity realized: PSU vested at maximum for McDonald (750,000 shares; $3,519,063 value); RSU vesting value realized $534,238 .
Equity Ownership & Trading Pressure Signals
- Quarterly RSU vesting through 12/16/2026 creates recurring supply events; insider trading policy blocks sales during closed windows and requires pre-clearance and prohibits hedging/pledging, reducing opportunistic or leveraged selling risk .
- Large beneficial ownership (8.6% of common; 6.8% combined voting power) indicates meaningful alignment; unvested RSUs (416,665) and PSUs (target 350,000) represent continued equity-linked incentives .
Investment Implications
- Alignment: Significant equity exposure, strict anti-hedging/pledging policy, and 6× salary ownership guideline support alignment; recurring RSU vesting could add technical supply near quarterly vest dates .
- Retention and optionality: Single-trigger full acceleration of equity upon termination without cause or for good reason, plus service counted for vesting, increases executive “walkaway” optionality; severance equals 12 months salary plus COBRA reimbursement, modest in cash but generous in equity acceleration (PSUs vest at target) .
- Pay-for-performance: Bonus plan tied to EBITDA/margin funded only on overperformance; 2024 payouts at ~16% of target highlight rigor; however, PSU maximum vesting in 2024 generated significant realized value despite multi-year TSR underperformance versus peers, warranting scrutiny of TSR goal calibration and vest timing/outcomes .
- Governance: Dual CEO/Chair role mitigated by Lead Independent Director and fully independent committees; no related-party transactions disclosed in 2024, and 100% board/committee attendance, supporting governance quality even amid performance challenges .