Form 4: Pineapple Financial COO Boosts Stake with Significant Share Purchases

Kendall Leo Marin, Chief Operating Officer, Director, and 10% Owner of Pineapple Financial Inc., has increased his direct beneficial ownership of common shares through multiple open market purchases in July 2025.

Summary

• Kendall Leo Marin, serving as COO, Director, and a 10% Owner of Pineapple Financial Inc. (PAPL), reported multiple acquisitions of the company's common shares.
• Transactions occurred on July 8, 2025, and July 10, 2025, totaling 10,100 common shares acquired.
• The purchase prices for these shares ranged from $0.09 to $0.10 per share.
• Following these reported transactions, Mr. Marin directly beneficially owns 2,291,923 common shares.
• The reported transactions were executed pursuant to a Rule 10b5-1(c) plan, indicating a pre-arranged trading strategy.
• Mr. Marin's total beneficial ownership excludes 126,652 stock options and 25,651 warrants.
• The stock options were granted on November 3, 2023, under the 2022 Omnibus Equity Incentive Compensation Plan, exercisable at $3.60 per share, with 25% vesting on the grant date and the remainder vesting in equal installments every six months over two years.

Sentiment

Score: 7

Explanation: The sentiment is positive due to significant insider buying by a key executive, signaling confidence. However, the low share price of the purchases could indicate a low current valuation, tempering the overall positive outlook.

Positives

• The Chief Operating Officer, Director, and 10% Owner increasing his direct stake in Pineapple Financial Inc. signals strong insider confidence in the company's future prospects.
• The purchases were made under a Rule 10b5-1(c) plan, which indicates a pre-planned and systematic approach to equity acquisition, often viewed favorably as it mitigates concerns about opportunistic trading.

Negatives

• The relatively low purchase price range of $0.09 to $0.10 per share for the common stock could suggest a low current market valuation for Pineapple Financial Inc.

Future Outlook

The stock options granted to Kendall Marin on November 3, 2023, are set to vest over a two-year period, with 25% having vested on the grant date and the remaining unvested options vesting in equal installments every six months thereafter, indicating future equity vesting events. The reported transactions were conducted under a Rule 10b5-1(c) plan, which outlines pre-arranged future equity transactions.

Industry Context

This insider transaction report reflects a specific executive's investment activity within Pineapple Financial Inc. and does not provide broader industry trends or competitive analysis.

Corporate Governance

Related Party Transactions

• Kendall Leo Marin, an insider (COO, Director, and 10% Owner) of Pineapple Financial Inc., purchased 10,100 common shares of the company from the open market on July 8 and July 10, 2025.

Stakeholder Impact

• Shareholders may view the increased insider ownership as a positive indicator of management's belief in the company's value and future prospects, potentially boosting investor confidence.

Next Steps

• Continued vesting of Kendall Marin's stock options in equal installments every six months, following the initial 25% vesting on November 3, 2023.

Key Dates

Recommendation

Keywords

Pineapple Financial Inc., PAPL, Kendall Marin, insider trading, Form 4, beneficial ownership, stock purchase, COO, director, 10% owner, Rule 10b5-1