CMPR CIMPRESS plc Insider Trading

CFO Sean Edward Quinn sold 27,989 shares ($2.9M) at $104.54 avg; holds 28,937 shares post-sale, retains 69,189 options.

Sean Edward Quinn, EVP and Chief Financial Officer of Cimpress plc, executed four separate sales on 2026-05-27 and 2026-05-28, totaling 27,989 shares for $2,925,909.42 at a blended average price of $104.54. This represents a 49.2% reduction in his non-derivative holdings (from 56,926 to 28,937 shares), yet his derivative holdings of 69,189 option shares remain intact post-transaction. His cross-ticker track record shows 6 prior sells with a 90-day well-timed rate of 100.00%, and all 5 of his prior trades at Cimpress were well-timed at the 90-day mark. The current stock price of $98.56 sits 7.1% below the 52-week high of $106.13, and the 30-day and 90-day changes of +21.0% and +34.9% respectively indicate strong recent momentum—a backdrop under which a substantial insider sale may warrant attention for directional signals.

CTO Wensveen executes complex one-day transaction: buys 10,000 shares while selling 19,251, netting position reduction at elevated price levels

Maarten Wensveen, CMPR's Chief Technology Officer, conducted a same-day mix of buying and selling that results in a net reduction of his shareholding. The sale tranches (totaling $1.79M) occurred at prices ranging from $90.73 to $94.13, while his purchase of 10,000 shares was at $46.20—a substantial price gap suggesting these may not be part of a coordinated strategy. His prior sales in late 2025 saw the stock rise in the months following, indicating those exits were poorly timed, yet he is selling again at prices well above where those prior exits occurred. The company remains profitable with growing quarterly revenues, though it trades at a stretched valuation multiple. This transaction is complex enough to warrant scrutiny: the divergent pricing between the buy and sell legs, combined with a net reduction despite the purchase component, suggests operational or personal factors rather than a straightforward conviction signal.

CFO Quinn Sean Edward buys 4,000 shares at blended $62.79 for $251,174.58 as CMPR stock trades -26.7% from 52-week high.

CFO Quinn Sean Edward executed 4 separate purchases totaling 4,000 shares for $251,174.58, raising his holdings to 36,484 shares (+12.3% increase). The purchases occurred at prices between $61.83–$63.00, at a blended average of $62.79, in a market environment where the stock trades at $61.21, down 26.7% from its 52-week high of $83.53. His prior purchase at this ticker on 2025-03-14 delivered +9.2% 90-day return, and across his full cross-ticker buy history, his average 90-day return has been +9.2% with a 100% win rate. This purchase signals CFO-level conviction in the current risk-reward at depressed valuations, though the company's elevated P/E of 43.11 and modest net income of $7.6M on $863.3M revenue warrant attention to whether current pricing reflects genuine opportunity or structural headwinds.

EVP & CTO Wensveen sold 22,830 shares at avg $68.36; post-sale stake down to 20,587 shares (-52.6%)

Wensveen Maarten, EVP & Chief Technology Officer, executed 3 separate sales totaling 22,830 shares for $1,560,605.84 on 2025-11-03, reducing his holdings by 52.6% to 20,587 shares. The transactions occurred at prices ranging from $68.24 to $70.74, a blended average of $68.36, above the current price of $64.72 but well below the 52-week high of $83.53. His prior sells at CMPR showed positive 90-day returns of +21.7% and +24.3%, indicating his past sales at this ticker preceded subsequent stock appreciation rather than declines. Current fundamentals show a P/E of 45.58 with net income of $7.6M on revenue of $863.3M, reflecting modest profitability relative to valuation. The timing relative to price trend—selling above current levels but 22.5% below the 52-week peak, during a period of recent strength (90-day return +16.6%)—provides limited directional signal about near-term conviction.

CFO Quinn Sean Edward bought 5,000 CMPR shares at $41.50 on 2025-03-14, raising stake to 20,224 shares (+32.8%).

Quinn Sean Edward, CMPR's CFO, purchased 5,000 shares at $41.50, expanding his holdings by 32.8% to 20,224 shares. The purchase occurred near the lower end of the 52-week range ($41.88–$101.04), at a point when the stock is -55.4% from its 52-week high and down 42.6% over 90 days. CMPR trades at a low P/E of 7.01 with recent quarterly revenue of $939.2M and net income of $61.1M, suggesting fundamental asset value may exceed current market perception. However, his prior trades at CMPR show a strong pattern of well-timed sells (3 of 3 measurable sales resulted in 90-day declines ranging from -18.1% to -20.4%), and his cross-ticker history confirms this pattern (100% well-timed rate on 6 prior sales). The timing and magnitude of this buy against a backdrop of recent stock weakness, combined with a CFO who has demonstrated consistent timing acumen on the sell side at this same ticker, warrants investor attention.

Director Scott J Vassalluzzo sold 316,056 shares at $79.10 for $25,000,029.60

Scott J Vassalluzzo, a Director, executed 4 separate sales totaling 316,056 shares for $25,000,029.60 on 2024-11-07. This represents a reduction of -73.1% vs pre-transaction holdings, leaving him with 116,442 shares post-transaction versus 432,498 shares prior. The magnitude and structure of these sales—four tranches at the identical blended average price of $79.10—warrant investor attention to understand the motivation and any underlying business context driving such a substantial director position reduction.

CEO Robert S Keane sells 71,019 shares of CMPR for $7.1M across 7 transactions, retains 987.2K shares

Robert S Keane, CEO and Chairman of Cimpress plc, executed 7 separate sales totaling 71,019 shares for $7,051,345.65 at a blended average price of $99.29 on August 29-30, 2024. The sale represents a 6.7% reduction in his pre-transaction holdings of 1,058,200 shares, leaving him with 987,181 shares post-transaction. At the current price of $94.85, the stock has declined 6.1% from its 52-week high of $101.04, where the CEO's transactions occurred near that peak. The company reported a net loss of $-3,978,000 in its latest quarter against revenue of $780,588,000, though annual revenue growth stands at 6.9% year-over-year. The CEO retains substantial holdings post-sale, preserving significant ongoing ownership alignment with shareholders.

CFO Quinn Sean Edward sells entire 24,093-share CMPR position (24.1K shares) for $2,372,685.31; complete exit from holdings.

Quinn Sean Edward, EVP and Chief Financial Officer of CIMPRESS plc, executed three separate sales totaling 24,093 shares for $2,372,685.31 on 2024-08-29, eliminating his entire shareholding (100.0% reduction). The sales occurred at prices ranging from $98.24 to $101.12, with a blended average of $98.48—near the current price of $98.88 and within 2.1% of the 52-week high of $101.04. This complete liquidation by the CFO is noteworthy given the company's fundamentals: revenue of $780,588,000 in the latest quarter, positive annual growth of 6.9%, and a favorable P/E of 5.54. Prior insider transactions at CMPR have not generated measurable performance outcomes, offering limited precedent for interpreting this timing relative to subsequent price movement. The full exit warrants investor attention as a shift in the officer's equity stake.