Charles Youakim
About Charles Youakim
Charles “Charlie” Youakim, age 48, is Sezzle’s co-founder, Executive Chairman, and Chief Executive Officer. He holds a Mechanical Engineering degree and an MBA from the University of Minnesota (Carlson) and has led Sezzle since 2016, after founding payments company Passport Labs in 2010 . Under his leadership, Sezzle delivered 2024 revenue growth of 70% and net income of $78.5 million, generated $40 million in operating cash flow, and executed $20 million in buybacks; the company also guided to over 55% pre-tax income growth for 2025 and announced a $50 million repurchase program . In Q3 2025 year-to-date, revenue grew to $320.4 million and net income to $90.4 million, with GMV up 65.2% year-to-date and 58.7% in Q3, reflecting scaling subscription products and On-Demand .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Sezzle Inc. | Co-Founder; Executive Chairman & CEO; Director | 2016–present | Architected BNPL product suite; led profitable growth and capital returns |
| Passport Labs, Inc. | Founder | Founded 2010 | Built payments software for transportation; introduced wallets/white-label systems (ParkChicago, ParkBoston, Toronto Green P) |
| Early career (engineering/software) | Engineer & Software Developer | Not disclosed | Technical foundation underpinning fintech product execution |
External Roles
| Organization | Role | Years | Notes |
|---|---|---|---|
| None disclosed | — | — | The proxy states Mr. Youakim does not currently hold other directorships |
Fixed Compensation
| Metric | 2023 | 2024 |
|---|---|---|
| Base Salary ($) | $514,423 | $536,510 |
| Bonus ($) | $0 | $0 |
| Stock Awards ($) | $1,168,691 | $463,920 (unrestricted stock under PSIP) |
| Option Awards ($) | $0 | $682,642 |
| Non-Equity Incentive (PSIP cash) ($) | $260,000 | $540,750 |
| All Other Compensation ($) | $325 | $291 |
| Total Compensation ($) | $1,943,439 | $2,224,113 |
Performance Compensation
Profit-Sharing Incentive Plan (PSIP)
| Year | Metric | Target Structure | Actual/Payout | Equity Portion | Vesting |
|---|---|---|---|---|---|
| 2023 | Adjusted pre-tax income | 0–100% payout range set at year start | Company payout at 50% of goal; Mr. Youakim cash $260,000 | None disclosed | N/A |
| 2024 | Adjusted net income | Pool = 10% of adjusted net income; individual payouts discretionary | Mr. Youakim cash $540,750 | $463,920 unrestricted stock issued Mar 20, 2025 | Unrestricted stock (no ongoing vest) |
Long-Term Incentive Plan (LTIP) – RSUs and Options
| Grant Type | Grant/Quantity | Exercise Price | Expiration | Vesting Schedule | Notes |
|---|---|---|---|---|---|
| RSUs (2023 LTIP) | 177,636 unearned RSUs outstanding at 12/31/2024 | N/A | N/A | 25% vest 1/1/2024; remaining quarterly thereafter | Value reference uses $42.63 12/31/2024 close |
| Options (2024 LTIP) | 64,818 unearned options | $11.38 | 4/1/2034 | 25% vest 4/1/2025; remaining quarterly thereafter | Issued 4/1/2024 |
| Options (2019/2020 historic) | 78,954 exercisable options | $5.32 | 7/27/2029 | 25% after 1 year, then monthly over 36 months | Historic grant schedule |
Equity Ownership & Alignment
| Item | Data |
|---|---|
| Total beneficial ownership | 14,766,249 shares; 43.48% of outstanding |
| Composition | Includes 14,671,089 shares held directly/through controlled entities/family trusts; options to purchase 95,160 shares |
| Pledged shares (RED FLAG) | 10,323,600 shares pledged as collateral for personal indebtedness |
| Pledging details | Schedule 13D/A discloses a $10 million Oppenheimer margin loan with 1,720,600 shares pledged (Aug 22, 2024), subject to margin/foreclosure rights |
| Company policy on hedging/pledging | Prohibits hedging, short sales, margin accounts; pledging permitted only with Audit & Risk Committee approval and capacity to repay without pledged stock; committee monitors pledges |
Outstanding Equity Awards at FY 2024 Year-End (Status)
| Category | Quantity | Terms |
|---|---|---|
| Exercisable options | 78,954 | $5.32 strike; expire 7/27/2029; historical time-based vest |
| Unexercisable options | 64,818 | $11.38 strike; expire 4/1/2034; service-based vest 25% on 4/1/2025, then quarterly |
| Unearned RSUs | 177,636 | Service-based vest 25% on 1/1/2024, then quarterly; value reference uses $42.63 close |
Employment Terms
| Provision | Details |
|---|---|
| Employment agreement | Dated June 1, 2019 |
| Base salary (set by agreement; adjusted by committee) | 2024 increased to $540,750 per proxy narrative |
| Notice period (company or executive termination other than cause) | 12 months’ advance written notice (or payment in lieu equal to regular compensation during notice period) |
| Change-of-control | If terminated in connection with or within 3 years after a change of control, all stock options immediately vest and become exercisable |
| Restrictive covenants | Proprietary information and inventions; non-compete and non-solicit of service providers, customers/prospects, and suppliers during employment and for 1 year post-termination |
| Clawback | Awards subject to forfeiture/disgorgement for misconduct, financial misstatement, non-compliance, or as required by law/listing standards |
Board Governance
- Roles: Executive Chairman and CEO; Director since 2016 .
- Independence: Board has a majority of independent directors (Brehm, East, Webster). Youakim and Paradis are executive directors .
- Committee membership: Mr. Youakim is not a member of Audit & Risk, Compensation, or Nominating & Corporate Governance committees .
- Committee leadership: All three committees comprise Brehm, East (Chair), and Webster; East is designated audit committee financial expert .
- Board leadership structure: Combined Chair/CEO role deemed appropriate by Board given company stage; majority independent Board provides oversight .
- Executive sessions: Independent directors meet at least twice annually without management .
- Attendance: Board met 14 times in 2024; all directors attended at least 75% .
Director Compensation (for non-executive directors; executives typically do not receive director fees)
| Component | Amount |
|---|---|
| Annual Board retainer | $60,000 |
| Audit & Risk Chair | $15,000 |
| Compensation or Nominating Chair | $7,500 |
| Audit & Risk member | $7,500 |
| Compensation or Nominating member | $3,750 |
Compensation Committee Analysis
- Philosophy: Competitive rewards aligned with strategic objectives and sustainable value creation; merit-based; market benchmarked .
- Consultant: FW Cook engaged in 2022 for benchmarking; plan to engage again in 2025 .
- Peer group: Committee reviews/sets benchmarking peer groups; specific companies not disclosed .
- Interlocks: None; no insiders on the committee .
Say-on-Pay & Shareholder Feedback
| Proposal | For | Against | Abstain | Non-Votes |
|---|---|---|---|---|
| 2025 Advisory Vote to Approve Executive Compensation | 22,065,307 | 195,097 | 47,550 | 5,998,762 |
Related Party Transactions
- Employment of relatives: CEO’s brother-in-law (David Myos) employed; total 2024 compensation ≈ $186,000; President’s brother (Nicholas Paradis) employed; total 2024 compensation ≈ $199,000; company states compensation consistent with comparable roles/tenure .
- Review process: Audit & Risk Committee reviews/approves related-party transactions; policy requires prompt disclosure of potential conflicts .
Performance & Track Record
| Metric | 2024 | 2025 YTD (Q3) |
|---|---|---|
| Revenue growth | +70% YoY (narrative) | $320.4M vs $172.9M (+85.3%) |
| Net income | $78.5M (10x YoY increase) | $90.4M vs $53.2M |
| GMV | — | $2,782,962K vs $1,684,797K (+65.2%) YTD; Q3 $1,047,299K vs $659,889K (+58.7%) |
| Capital returns | $20M buybacks in 2024; $50M program announced early 2025 | |
| Recognition | Forbes ranked Sezzle 3rd among America’s Most Successful Mid-Cap Companies |
Risk Indicators & Red Flags
- Pledging risk: CEO has pledged a substantial number of shares (10,323,600) as collateral; company risk factors warn foreclosure sales or perceived sales by pledgees could adversely impact stock price and control; only officer/director with pledged shares is the CEO .
- Combined Chair/CEO: Dual role mitigated by majority-independent board and independent committees; still a governance consideration .
- Legal proceedings: Sezzle filed antitrust suit against Shopify; Shopify moved to dismiss; hearing scheduled Dec 8, 2025 .
- Trading arrangements: No adoption/termination of Rule 10b5-1 or non-Rule 10b5-1 plans in Q3 2025 by officers/directors .
- Historic tax gross-up: Company paid $56,037 in 2022 for legal fees (and associated tax gross-ups) related to CEO’s personal counsel in merger discussions; company considered it a business expense .
Equity Ownership Guidelines & Securities Policy
- Securities trading policy: Prohibits hedging and short-selling; pledging only with Audit & Risk Committee approval and capacity to repay without pledged shares; committee monitors pledged positions and considers market impact in approvals .
Employment & Contracts — Additional Details
- Benefits: Participates in broad-based benefits; 401(k) match reflected in “All other compensation” .
- Severance economics: Not expressed as salary+bonus multiples; economic protection is primarily the 12-month notice or payment in lieu and option vesting upon change of control if terminated in connection with the event .
Investment Implications
- Alignment vs. liquidity risk: Very high ownership (43.48%) aligns CEO with shareholders, but significant pledging (10.3M shares) introduces potential selling pressure and margin-call risk in adverse markets; the company’s policy and committee oversight partially mitigate but do not eliminate this risk .
- Pay-for-performance: PSIP tied to profitability (adjusted pre-tax/net income) with both cash and unrestricted stock elements; LTIP is predominantly service-based vesting RSUs and options, supporting retention with clear vest schedules; absence of complex TSR metrics reduces measurement opacity but may limit market-relative alignment .
- Governance: Combined Chair/CEO role with independent committees and regular executive sessions provides oversight, though independence optics remain a consideration; strong say-on-pay support in 2025 indicates investor approval of current compensation practices .
- Execution momentum: Sustained GMV, revenue, and net income growth, plus capital returns, point to operational discipline; ongoing litigation and rising credit loss provisions tied to underwriting changes should be monitored for profitability durability and risk-adjusted returns .