Drew Green
About Drew Green
Drew Green (age 49) is an independent director and Chairman of the Board at Pineapple Financial Inc. (PAPL), serving since May 6, 2019 . He is an award‑winning CEO and entrepreneur known for scaling INDOCHINO between 2015–2024, securing over $100M in strategic capital and broad commercial partnerships; he is also a board member at York University, his alma mater .
Past Roles
| Organization | Role | Tenure | Committees/Impact |
|---|---|---|---|
| INDOCHINO | Chief Executive Officer | 2015–2024 | Led rapid expansion, raised $100M+ from Madrona, Highland, Dayang, Mitsui, Postmedia; built alliances with major leagues and media partners . |
| EMERGE Commerce | Chairman, major shareholder | Not disclosed | Leads the company that acquired the multi‑merchant marketplace he founded . |
| FloNetwork (acquired by DoubleClick) | Leadership role | Not disclosed | Prior leadership experience pre‑acquisition . |
| DoubleClick (acquired by Google) | Leadership role | Not disclosed | Prior leadership experience pre‑acquisition . |
| SHOP.COM (acquired by Market America) | Leadership role | Not disclosed | Prior leadership experience pre‑acquisition . |
External Roles
| Organization | Role | Public/Private | Notes |
|---|---|---|---|
| American Aires Inc. | Director and Chairman | Public (OSC jurisdiction) | Company was under a cease trade order (May 6, 2022) for filing deficiencies; revoked Mar 10, 2023 (resolved) . |
| EMERGE Commerce | Chairman | Public (TSXV) | Leads as Chairman and major shareholder . |
| York University | Board member | Non‑profit/Academic | Serves on the board; provides scholarships . |
Board Governance
- Independence: The Board determined that Drew Green is independent under NYSE American rules .
- Committees and roles:
- Audit Committee: Chair (members: Paul Baron, Drew Green (Chair), Tasis Giannoukakis) .
- Compensation Committee: Member (with Paul Baron, Tasis Giannoukakis) .
- Nominating & Corporate Governance Committee: Member (with Paul Baron, Tasis Giannoukakis) .
- Board leadership: Chairman of the Board .
- Tenure: Director since May 6, 2019 .
- Attendance/engagement: Meeting attendance rates not disclosed in the filings reviewed.
Governance signals:
- Audit Committee chairing by an independent director with stated financial literacy across members .
- Concentration of committee roles (member of all three key committees) can be a workload/oversight concentration risk .
- Entered into a voting agreement to support 2025 special meeting proposals (share issuance and transfer restriction removal), covering 34,615 “subject shares,” indicating active engagement with capital strategy .
Fixed Compensation
| Component | Amount/Terms | Notes |
|---|---|---|
| Board fee (cash) | $7,887 per month | Paid under an agreement for board fees to Drew Green . |
| Committee chair/member fees | Not disclosed | — |
| Meeting fees | Not disclosed | — |
Performance Compensation
| Award Type | Grant/Status | Quantity/Strike | Vesting/Terms |
|---|---|---|---|
| RSUs | Granted and exercisable as of July 16, 2025 | 11,092 RSUs (nil exercise price) | Vested/exercisable as of 2025‑07‑16 . |
| Stock options | Granted | 10,000 options @ $1.30 | Options reported as immediately vesting on Form 4; grant aligns with July 16, 2025 awards . |
| Stock options (legacy) | Outstanding | 5,107 options @ $72.00 | Legacy options outstanding (post reverse split) . |
| Warrants (legacy) | Outstanding | 1,282 warrants @ C$58.60 | Legacy warrants outstanding (post reverse split) . |
Performance metric framework: No disclosure of director performance metrics (e.g., TSR, EBITDA, ESG) tied to equity/fees for directors was found in the reviewed filings.
Other Directorships & Interlocks
| Company | Role | Committee Roles | Interlock/Conflict Notes |
|---|---|---|---|
| American Aires Inc. | Director & Chairman | Not disclosed | Historical regulatory issue (cease trade order; revoked), a governance risk marker at another issuer . |
| EMERGE Commerce (TSXV) | Chairman | Not disclosed | External leadership role; time/overboarding considerations not addressed in PAPL filings . |
Expertise & Qualifications
- Capital formation and scaling: Led INDOCHINO’s growth with $100M+ in strategic capital and major brand alliances .
- Public company board leadership: Chair roles at multiple public companies; broad entrepreneurship background .
- Financial oversight: Chairs PAPL’s Audit Committee; all members assert financial statement literacy per charter disclosures .
- Academic/community engagement: Board member at York University; scholarship programs in his name .
Equity Ownership
As of the September 15, 2025 record date (latest proxy):
| Item | Amount/Terms | Notes |
|---|---|---|
| Beneficial ownership – Common Shares | 62,096 | 4.61% of 1,345,941 shares outstanding . |
| RSUs (vested/exercisable 7/16/2025) | 11,092 | Nil exercise price; exercisable as of 7/16/2025 . |
| Options (legacy) | 5,107 @ $72.00 | Outstanding options . |
| Options (new) | 10,000 @ $1.30 | Outstanding options . |
| Warrants (legacy) | 1,282 @ C$58.60 | Outstanding warrants . |
Historical reference (January 17, 2025): 820,097 shares (9.31%) including 102,138 options @ $3.60 and 25,651 warrants @ C$2.93 (pre subsequent corporate actions), illustrating dilution/structural changes over 2025 .
Insider Trades
| Date | Security | Transaction | Terms/Notes |
|---|---|---|---|
| 2025‑07‑16 | RSUs | Grant | 11,092 RSUs; exercisable as of grant date . |
| 2025‑07‑16 | Stock options | Grant | 10,000 options @ $1.30; options reported as vesting immediately (Form 4) . |
Governance Assessment
-
Strengths
- Independent board leader with deep capital markets and operating experience; chairs the Audit Committee and serves on all three key committees, suggesting high engagement and oversight capacity .
- Clear skin‑in‑the‑game via common shares and vested equity awards; entered a voting agreement to support a pivotal capital transaction, signaling alignment with the company’s financing strategy .
-
Watch items / potential red flags
- Unique board cash fee arrangement ($7,887/month) while serving on the Compensation Committee raises independence optics; no explicit recusal disclosed for compensation decisions involving his fees .
- Heavy committee concentration (on all three key committees) may reduce segregation of duties and increase key‑person dependence in governance .
- External commitments include chair roles at other public companies; one external issuer (American Aires) had a cease trade order (since revoked), which is a governance risk marker in his track record .
- Support for large share issuance and removal of transfer restrictions to execute a $100M crypto‑token treasury strategy (INJ) introduces dilution and market‑price risks; while strategic, investor alignment depends on risk tolerance for digital asset exposure .
-
Related‑party and conflicts
- No related‑party transactions disclosed for Green beyond board fees; however, his seat on the Compensation Committee while receiving unique board fees represents a perceived conflict risk if not managed via recusal or independent review .
- The company maintains a related‑person transaction policy overseen by the Audit Committee (which Green chairs), underscoring the need for careful governance process when matters involve directors .
Overall, Green brings strong capital markets/operator credentials and is highly engaged in PAPL’s governance, but investors should monitor compensation governance (unique fees/committee membership), committee workload concentration, and external commitments given prior regulatory issues at an outside issuer .