PBI PITNEY BOWES INC /DE/ Insider Trading

CEO Kurt James Wolf sold 522,141 shares for $8,878,441.94 (blended avg $17.00) via 10b5-1 plan; post-transaction holdings 217,930 shares (-70.6%).

Kurt James Wolf, President & CEO of Pitney Bowes Inc, executed 6 separate sales totaling 522,141 shares for $8,878,441.94 across July 2–7, 2026, reducing his holdings by 70.6% from 740,071 to 217,930 shares. This transaction is part of a pre-arranged 10b5-1 trading plan adopted on 2025-11-10, meaning the sales were scheduled rather than discretionary timing decisions. The stock currently trades at $17.04, within 6.6% of its 52-week high of $18.25, and the company shows modest fundamentals with a P/E of 13.74 and annual revenue decline of 6.6%. While Wolf's cross-ticker track record shows prior sells averaged +57.7% returns over 90 days, his five most recent same-ticker transactions at PBI (from June 10–12) have no measurable outcomes yet, limiting inference about this series' outcome. The 10b5-1 structure removes timing as an analytical variable; investors should monitor whether the substantial reduction in CEO ownership signals a permanent directional shift or reflects portfolio rebalancing under a pre-set schedule.

CEO Kurt James Wolf sold 814.8K shares across 6 sales on 2026-06-10/12 for $13,964,971.38; pre-arranged 10b5-1 plan.

Kurt James Wolf, President & CEO of Pitney Bowes, executed 6 separate sales totaling 814,817 shares for $13,964,971.38 at blended average price $17.14 across June 10–12, 2026. This transaction was conducted under a pre-arranged 10b5-1 trading plan adopted on 2025-11-10, making it scheduled rather than discretionary. The sales reduced his holdings from 1,079,739 shares to 264,922 shares, a reduction of 75.5% of his pre-transaction position. The stock currently trades at $17.32, slightly below the 52-week high of $17.59, and has appreciated 12.9% over 30 days and 70.8% over 90 days. His cross-ticker track record shows 20 prior sells with an average 90-day return of +54.8%, though prior same-ticker outcomes are not yet measurable for most recent sales at this ticker. The company's fundamentals show a revenue decline of 6.6% year-over-year alongside P/E of 13.97, warranting attention to whether broader operational headwinds influenced the plan's timing or structure.

PBI CEO Kurt James Wolf sold 243,938 shares for $3,823,484.22 on 2026-05-27 via pre-arranged 10b5-1 plan; retains 338,256 shares.

Kurt James Wolf executed two separate sales totaling 243,938 shares at $15.67 on 2026-05-27 for $3,823,484.22, reducing his holdings by 41.9%. This transaction is part of a pre-arranged 10b5-1 trading plan adopted on 2025-11-10, meaning it is scheduled rather than discretionary. The sales occurred near the upper end of the 52-week range ($8.95–$16.56); current price is $15.84. At the same ticker, Wolf's prior five sales show mixed near-term outcomes, with 30-day and 90-day returns ranging from -2.8% to +5.4%. Investors should note the magnitude of the reduction—243.9K shares—but the scheduled nature of the plan removes any inference about timing or strategic judgment tied to current valuations.

CEO Wolf sold 40,476 shares at $15.62 under pre-arranged 10b5-1 plan; retains 360,210 shares post-sale.

Kurt James Wolf, President & CEO of Pitney Bowes, executed 2 separate sales totaling 40,476 shares for $632,316.08 at $15.62 per share on 2026-05-22. This transaction was part of a pre-arranged 10b5-1 trading plan adopted on 2025-11-10, meaning the sales were scheduled rather than discretionary decisions. Wolf retains 360,210 shares post-transaction, representing a 10.1% reduction in holdings. The current stock price of $15.51 is 6.3% below the 52-week high of $16.56, and the company reports negative annual revenue growth of -6.6% with a P/E of 12.51. Prior trades by Wolf at PBI show mixed near-term performance, with sales on 2026-05-08 returning -2.8% over 30 days and the most recent prior sale on 2026-05-06 returning +5.4%.

Pitney Bowes President & CEO Kurt James executes $29.5M stock sale across three days; stock up sharply recently but prior exits poorly timed.

Kurt James, the President and CEO of Pitney Bowes, sold nearly 2 million shares across three consecutive trading days in early May, totaling nearly $29.5 million in proceeds. This is a substantial exit representing roughly 9.5% of his holdings at the start of the transaction sequence. The timing is notable: the stock has climbed sharply over the prior three months and is trading just below its 52-week high, positioning this sale near a recent peak. However, this sale reflects a consistent pattern for James—across his five prior sales in Pitney Bowes, the stock has risen noticeably in the months following each exit, meaning all of his previous exits were poorly timed from a long-term perspective. The company remains profitable with recent quarterly earnings, but revenue declined year-over-year, creating a mixed fundamental picture. James has never made an open-market purchase in the three-year filing window, making this an exclusively selling insider, which combined with the poor timing of his prior exits suggests caution rather than conviction about the company's near-term direction.

Pitney Bowes CEO Wolf Kurt James sells 200,208 shares for $2.2M under 10b5-1 plan

CEO Wolf Kurt James executed 4 separate sales totaling 200,208 shares for $2,217,534.53 at blended average price of $11.08, executed on April 1-2, 2026. Post-transaction holdings decreased to 539,618 shares from 739,826 shares, representing a -27.1% reduction in his equity stake. This sale is part of a pre-arranged 10b5-1 trading plan adopted on 2025-11-10, meaning execution follows a scheduled program rather than discretionary decision-making. The magnitude of the stake reduction warrants investor attention as a material change in CEO exposure to company equity.

Director Rosenthal bought 4,000 PBI shares at $10.22; holdings +80% to 9.0K shares; P/E 3.63, annual revenue down 6.6%.

Rosenthal Brent D, a director, purchased 4,000 shares at $10.22 on 2026-03-13, increasing his holdings by 80.0% from 5,000 shares to 9,000 shares. The transaction occurs at a price significantly below the 52-week high of $12.79 (-18.9%), and the company trades at a historically low P/E of 3.63 amid declining fundamentals: annual revenue contracted 6.6% year-over-year, though the latest quarter delivered $459.7M in revenue and $52.0M in net income. His prior two buys at this ticker (both on 2025-11-25) both achieved positive 90-day returns of +3.8%, suggesting some timing capability at this specific stock, though a 2025-09-03 buy returned -20.6% at the 90-day mark. The current share price of $10.37 is only $0.15 above the transaction price, leaving minimal near-term appreciation, and his cross-ticker buy history shows an average 90-day return of -3.2% despite a 71.43% win rate. This purchase warrants monitoring to determine whether the depressed valuation and modest recent precedent of well-timed buys at PBI will extend to this transaction.

CEO Wolf Kurt James sells 150,000 PBI shares for $1,556,550 via scheduled 10b5-1 plan; retains 557,637 shares post-sale

Wolf Kurt James, President & CEO of Pitney Bowes, executed two separate sales totaling 150,000 shares at $10.38 on 2026-03-11 for $1,556,550.00 under a pre-arranged 10b5-1 trading plan adopted on 2025-11-10. This is a non-discretionary, scheduled transaction, so the timing reflects the plan's calendar, not a judgment about current market conditions. Post-sale, James retains 557,637 shares, representing a 21.2% reduction from his pre-transaction holding of 707,637 shares. As the company's top executive, his material reduction in equity stake warrants baseline investor awareness, though the mechanistic nature of 10b5-1 execution removes any inference about conviction or market timing from this particular filing.

Director Brimm buys 4,000 PBI shares at $10.78; position increased 32.0%; pattern repeats late-October buys with +0.8–0.9% 90-day returns.

Peter C Brimm, a director, purchased 4,000 shares of Pitney Bowes at $10.78 on 2026-02-27, growing his holding from 12,500 to 16,500 shares—a 32.0% increase in stake size. This mirrors his transaction pattern: two prior open-market buys at the same ticker on 2025-10-31 generated +0.8% and +0.9% returns over 90 days, both well-timed at the 90-day mark. His cross-ticker track record shows a 100% 90-day win rate across 2 prior buys despite a -2.9% average 30-day return, suggesting patience in his buying approach. Against current fundamentals (P/E 3.69, -6.6% annual revenue growth), the stock trades at $10.56—17.4% below its 52-week high—but no scheduled plan or corporate catalyst context is evident, so this transaction reflects a discretionary choice to accumulate further at a depressed price relative to recent highs.

Wolf Kurt James (CEO) sold 150,000 shares at $10.30 via pre-arranged 10b5-1 plan

Wolf Kurt James, President & CEO of Pitney Bowes Inc, executed 2 separate sales totaling 150,000 shares for $1,545,750.00 on 2026-02-23, reducing his holdings from 721,137 shares to 571,137 shares. The transaction was conducted at $10.30 per share under a 10b5-1 trading plan adopted on 2025-11-10, meaning the sale was scheduled in advance rather than discretionary. This represents a reduction of approximately 20.8% of his pre-transaction holdings. Since the transaction is pre-arranged and not discretionary, no timing inference or conviction signal can be drawn from the execution date.