Shubha Dasgupta
About Shubha Dasgupta
- Chief Executive Officer and Director of Pineapple Financial Inc. since October 16, 2015; age 44 per 2025 proxy .
- Background: Entered the mortgage industry in 2008; led Pineapple’s technology-led brokerage model and built the proprietary MyPineapple/Pineapple+ CRM/origination platform; recognized on Canadian Mortgage Professional Hot List and Mortgage Global 100; past President of CMBA Ontario board (2021) .
- Recent business performance indicators disclosed by PAPL: mortgage originations of $690.0M for the six months ended Feb 28, 2025 (+17.6% YoY); net loss improved by ~$0.38M year-over-year to $(1.17)M in the period; management noted going-concern uncertainties remain, dependent on financing and execution .
Past Roles
| Organization | Role | Years | Strategic impact |
|---|---|---|---|
| Pineapple Financial Inc. (formerly CLC Network) | Chief Executive Officer and Director | Oct 2015 – Present | Led build-out of proprietary data-driven CRM/origination platform; scaled network of >500 brokers; positioned firm as tech-enabled mortgage brokerage |
| Bedrock Financial Group | Mortgage Broker | Aug 2008 – Oct 2016 | Front-line origination experience that informed Pineapple’s platform and brokerage model |
External Roles
| Organization | Role | Years | Strategic impact |
|---|---|---|---|
| Canadian Mortgage Brokers Association (CMBA) Ontario | President (after prior board service) | 2021 | Industry leadership; network access and policy engagement in Canadian mortgage market |
| Community/non-profit initiatives | Philanthropic leader (e.g., CMI Cancer Fighters co-founder/chair) | Ongoing | Brand reputation and industry network development |
Fixed Compensation
| Metric (USD) | FY 2023 | FY 2024 |
|---|---|---|
| Base Salary | $188,256 | $177,816 |
| Bonus | $0 | $0 |
| Stock Awards | $0 | $0 |
| Option Awards | $0 | $0 |
| Non-Equity Incentive Plan | $0 | $0 |
| All Other Compensation | $11,357 | $10,669 |
| Total | $199,613 | $188,485 |
Notes: The 2025 special proxy indicates forthcoming employment agreements will keep salary/bonus “consistent with” prior compensation disclosed in the April 25, 2025 S-1, with six months salary/benefits if terminated without cause, customary covenants, and participation in a management incentive program (see Employment Terms) .
Performance Compensation
- No annual cash bonus paid for 2023 or 2024; no non-equity incentive plan compensation disclosed .
- No PSUs or performance metric-linked equity awards disclosed in 2023–2024 filings .
| Incentive Type | Metric(s) | Weighting | Target | Actual | Payout | Vesting |
|---|---|---|---|---|---|---|
| Annual bonus | Not disclosed | N/A | N/A | N/A | $0 (2023, 2024) | N/A |
| Performance stock (PSUs) | Not disclosed | N/A | N/A | N/A | N/A | N/A |
Equity Ownership & Alignment
- Share ownership snapshots show significant “skin in the game,” with changes reflecting share count changes and corporate actions.
| As-of Date (Record) | Shares Beneficially Owned | % Outstanding | Composition / Notes |
|---|---|---|---|
| Jan 17, 2025 | 998,457 | 11.34% | Includes 126,652 options @ $3.60 and 25,641 warrants @ C$2.93; held via 5032771 Ontario Inc. |
| May 23, 2025 | 998,447 | 4.97% | Same option/warrant breakdown noted for this table; total outstanding 20,092,020 |
| Sep 15, 2025 | 82,560 | 6.13% | Includes: 6,333 options @ $72.00; 1,282 warrants @ C$58.60; 12,638 RSUs (nil exercise price) exercisable as of Jul 16, 2025; 20,000 options @ $1.30; mix reflects reverse split/new grants |
Vested vs. unvested and exercisability pointers:
- Options: Legacy grant expiring June 14, 2026 (pre-reverse-split price $3.60 shown in FY2024 table); later post-split figures reflect adjusted strikes; plus a 2025 grant at $1.30 noted in Sep 2025 table .
- RSUs: 12,638 RSUs were “exercisable/issuable as of July 16, 2025” (nil exercise price) .
- Pledging/hedging: No pledging or hedging disclosures identified for Dasgupta; holdings primarily via 5032771 Ontario Inc. .
Insider selling pressure signals:
- RSUs vesting/issuable Jul 16, 2025 (12,638) and option grants may create potential supply if sold, but filings do not disclose sales activity; only positions and terms .
Stock ownership guidelines:
- No director/executive ownership guideline disclosures identified in reviewed filings.
Employment Terms
| Term | Key Provisions |
|---|---|
| Employment Agreement (to be entered prior to Escrow Deadline per SPA Amendment) | Salary/bonus consistent with prior S-1 disclosure; reimbursement of reasonable out-of-pocket expenses; customary benefits/PTO; six months salary and benefits if terminated without cause; customary IP/confidentiality and non‑solicitation covenants; eligibility for management incentive program (Exhibit A to SPA Amendment) . |
| Change-of-Control | Not specified in reviewed disclosures . |
| Clawback | Not specified in reviewed disclosures. |
| Non-compete | Not specified; “customary covenants” include IP and non‑solicit . |
Board Governance
- Board service: CEO and Director since Oct 16, 2015 .
- Board structure (2025 AGM slate): Shubha Dasgupta (CEO/Director), Kendall Marin (President/COO/Director), Drew Green (Chair), Paul Baron (Director), Tasis Giannoukakis (Director) .
- Independence: Board determined Baron, Giannoukakis, and Green are independent; Dasgupta is non-independent executive .
- Committees and roles:
- Audit Committee: Drew Green (Chair), Paul Baron, Tasis Giannoukakis (all independent) .
- Compensation Committee: Drew Green, Paul Baron, Tasis Giannoukakis (independent; empowered to select independent advisors) .
- Nominating & Corporate Governance: Drew Green, Paul Baron, Tasis Giannoukakis .
- Dual-role implications: CEO is not Chair (Chair is an independent director), and all key committees are independent—mitigating typical CEO/Chair concentration risks; CEO is not listed as serving on committees .
- Meeting attendance rate/Lead Independent Director/executive sessions: Not disclosed in reviewed proxies.
Director Compensation
- Policy: “To date, we have not compensated our directors for their service,” with exceptions: Drew Green receives $7,887/month; Kia Besharat (brother of then-director Nima Besharat) previously received $3,943/month until Feb 2022 .
- Implication for Dasgupta: No additional director retainer beyond executive compensation noted .
Performance & Track Record
- Business indicators: Mortgage originations $690.0M in 6M ended Feb 28, 2025 (+17.6% YoY); net loss improved to $(1.17)M from $(1.54)M YoY .
- Company-level headwinds: Going-concern risks disclosed in S-1; need for financing; listing/compliance risks highlighted earlier in 2025 (NYSE American suspension notice May 14, 2025; appeal planned) .
- Awards/recognition: Mortgage Global 100; Canadian Mortgage Professional Hot List; industry leadership roles .
Related Party Transactions
- No related party transactions disclosed involving Dasgupta personally in reviewed filings. A director-affiliated advisory agreement (Centurion One Capital Corp.; CEO is director Nima Besharat) was disclosed; not attributable to Dasgupta .
Compensation Committee Analysis
- Composition: All independent (Green, Baron, Giannoukakis) with authority to engage independent consultants .
- Consultant conflicts/peer groups/target percentiles: Not disclosed in reviewed filings.
- Program design observations from disclosures: 2023–2024 NEO pay largely fixed salary with de minimis “other” comp; no disclosed annual bonus or performance-equity metrics; SPA Amendment introduces a management incentive program prospectively .
Vesting Schedules and Equity Instruments Detail
| Instrument | Quantity | Strike/Terms | Vesting/Status | Expiration |
|---|---|---|---|---|
| Stock options (legacy) | 126,652 | $3.60 | Outstanding per FY2024 year-end table | Jun 14, 2026 |
| RSUs | 12,638 | Nil exercise price | Became issuable/exercisable as of Jul 16, 2025 | Not stated |
| Stock options (post-split adjusted) | 6,333 | $72.00 | Outstanding | Not stated |
| Warrants (post-split adjusted) | 1,282 | C$58.60 | Outstanding | Not stated |
| Stock options (newer grant) | 20,000 | $1.30 | Outstanding | Not stated |
Note: Post-split figures reflect corporate actions in 2025; filings present both pre- and post-split instruments at different times. Always refer to the as-of date/filing context for comparability .
Equity Ownership & Alignment – Additional Notes
- Beneficial ownership through 5032771 Ontario Inc. (entity controlled by Dasgupta) .
- No pledging/hedging policy disclosures identified; no stock ownership guideline disclosures identified in reviewed materials.
Employment Contracts, Severance, and Change-of-Control Economics
- Severance: Six months salary and benefits upon termination without cause (per SPA Amendment framework for new agreements) .
- Change-of-control: Not specified.
- Clawbacks/tax gross-ups/deferred comp/pension/SERP: Not disclosed in reviewed materials .
- Non-solicit/IP/confidentiality: Customary covenants included .
Say-on-Pay & Shareholder Feedback
- No advisory say-on-pay votes disclosed in the 2025 annual meeting proxy (agenda limited to director elections and auditor ratification) .
Other Directorships & Interlocks
- Public company board roles for Dasgupta: None disclosed.
- Non-profit/industry boards: CMBA Ontario President; other community roles noted .
- Interlocks/conflicts: Not disclosed for Dasgupta.
Risk Indicators & Red Flags
- Company-level: Going-concern disclosure; reliance on external financing; NYSE American listing compliance issues identified in May 2025 (suspension notice; appeal pending); potential dilution from securities programs (EPA/S-1 offerings) .
- Executive/legal: No legal proceedings cited for Dasgupta; Section 16 compliance noted as timely for insiders .
- Compensation design: 2023–2024 showed no disclosed performance-based pay elements; prospective management incentive plan may alter pay mix .
Investment Implications
- Pay-for-performance alignment: Historical compensation indicates predominantly fixed cash with no disclosed annual incentive metrics; prospective “management incentive program” may add at-risk components, but specifics are not yet disclosed—limiting current visibility into performance alignment .
- Retention risk: Six-month severance is modest; absence of disclosed CoC protections or long-dated performance equity may present retention considerations in volatile market conditions; however, meaningful share/option/RSU holdings indicate alignment and potential retention tether via equity .
- Trading signals/overhang: RSUs that became issuable in July 2025 and option tranches could contribute to periodic selling pressure if monetized; broader company capital plans (EPA, unit/warrant offerings) introduce dilution overhang and price volatility .
- Governance quality: Separation of CEO and Chair and fully independent key committees mitigate dual-role concerns; majority-independent board structure supports oversight .
- Company execution backdrop: While originations improved and losses narrowed in 1H FY2025, going-concern language and listing risks underscore macro/capital-structure headwinds—factors to consider when inferring incentives and potential dilution pathways tied to capital raises .
Sources
- 2025 Special DEF 14A (Sep 29, 2025): ownership table; RSUs/options/warrants detail; employment agreement terms .
- 2025 DEF 14A (Feb 21, 2025): biographies; compensation tables; outstanding equity awards; board/committee composition; independence; related party policy .
- 2025 DEF 14A (May 27, 2025): ownership table; share count context .
- 2025 S-1 (Apr 25, 2025): going concern; capital programs; offering structure; business and performance metrics .
- 8-K (Feb 27, 2025): executive signature, general context .