CTLP CANTALOUPE, INC. Insider Trading

CFO Scott Matthew sells 62,830 shares of CTLP for $667.9K, reducing holdings 54.2%

Stewart Scott Matthew, Chief Financial Officer of CANTALOUPE, INC., sold 62,830 shares at $10.63 on 2025-09-18, reducing his holdings from 115,839 shares to 53,009 shares—a 54.2% reduction in his position. At the transaction price of $10.63, the stock was near its 52-week range and only 5.1% below the 52-week high of $11.15, suggesting the sale occurred at a relatively favorable price point relative to recent historical levels. The company posted net income of $-919,000.00 in the latest quarter while generating $80,853,000.00 in revenue with annual growth of 12.6%, indicating operational profitability challenges despite top-line growth. A substantial insider stake reduction of this magnitude by the CFO warrants monitoring of the company's near-term financial performance and whether this reflects confidence constraints or capital reallocation decisions.

CTO Singal Gaurav sold 200,000 shares of CTLP at $10.63, reducing stake by 83.1% to 40.5K shares

Chief Technology Officer Singal Gaurav executed a substantial reduction in his CANTALOUPE, INC. holdings, selling 200,000 shares at $10.63 on 2025-09-18 for a total value of $2,126,000.00, leaving him with 40.5K shares post-transaction. This represents a -83.1% reduction relative to his pre-transaction holdings of 240.5K shares. The sale price of $10.63 sits -4.7% from the 52-week high of $11.15, within the 52-week range of $6.33–$11.15. The company's recent fundamentals show strong profitability—$49.2M net income on $75.4M quarterly revenue with +12.6% annual revenue growth and a P/E of 6.95—suggesting operational health, but the magnitude of the CTO's stake reduction (from 240.5K to 40.5K shares) warrants investor attention to understand the rationale behind such a material portfolio adjustment.

Director Lisa P. Baird bought 6,000 CTLP shares at $7.42 on 2024-09-27; stock now at $7.87 (+13.7% in 30d)

Baird purchased 6,000 shares for $44,520.00 at $7.42, increasing her holdings from 91,319 to 97,319 shares (+6.6% position growth). The stock has appreciated +13.7% over 30 days and +20.3% over 90 days since the trade, currently trading near its 52-week high of $7.87. Across her prior open-market buy at CTLP in February 2024, the insider's cross-ticker track record shows a 100% 90-day win rate with an average 90-day return of +1.9%, and her February purchase was similarly well-timed (90d return +1.9%). The company's fundamentals show $67.9M revenue in the latest quarter, $4.7M net income, +10.2% annual revenue growth, and a P/E of 23.85. The timing of this purchase—with the stock now at its 52-week high—and the consistent pattern of her prior buy completing with positive returns warrant close attention to her conviction level and any forward-looking statements about company trajectory.

Director Bergeron Douglas purchased 284,000 shares at blended average $7.40 across 3 transactions, increasing stake to 462,319 shares (+159.3%)

Bergeron Douglas, a Director at Cantaloupe Inc., executed 3 separate purchases totaling 284,000 shares for $2,100,834.84 between September 26 and September 30, 2024. The blended average purchase price of $7.40 is aligned with the current market price of $7.40 and sits within the 52-week range of $5.79–$7.83. The purchases more than doubled his holding from 178,319 shares to 462,319 shares, representing a 159.3% increase in his equity stake. The company is currently valued at $540.1M market cap with trailing P/E of 22.42 and reported latest-quarter revenue of $67.9M with net income of $4.7M, indicating profitability and a 10.2% year-over-year revenue growth rate.

CEO Venkatesan Ravi bought 8,000 shares of CTLP at $6.30 on 2024-09-13, bringing holdings to 136.7K shares.

Venkatesan Ravi, the Chief Executive Officer, purchased 8,000 shares at $6.30 on 2024-09-13, increasing his holdings by 6.2% to 136.7K shares. The transaction occurred at a price 0.8% below the current market price of $6.35 and notably 18.9% below the 52-week high of $7.83, reflecting the stock's recent weakness (-8.8% over 30 days, -6.5% over 90 days). Reviewing his prior open-market history at CANTALOUPE, Ravi's two previous purchases at this ticker (February 2024 and September 2023) both achieved positive 90-day returns of +4.5% and +18.5% respectively, establishing a 100% win rate on those transactions. The company shows solid operational health with annual revenue growth of 10.2%, quarterly revenue of $67.9M, and positive net income of $4.7M, though the current P/E of 19.24 reflects elevated valuation at a time when the stock is near its 52-week lows.