BILL BILL Holdings, Inc. Insider Trading

CPO Michael Cieri sells 32,875 shares for $1.2M at BILL via pre-arranged 10b5-1 plan; retains 997 shares plus 154,770 RSUs.

Michael Cieri, Chief Product Officer, executed 3 separate sales totaling 32,875 shares for $1,204,663.34 on 2026-05-29 under a pre-arranged 10b5-1 trading plan adopted on 2025-12-02, reducing his non-derivative holdings from 33,872 shares to 997 shares. The sales occurred at prices ranging from $35.68 to $37.10, with a blended average of $36.64, while the stock currently trades at $33.18—down 42.0% from its 52-week high of $57.21. The transaction is scheduled under a 10b5-1 plan rather than discretionary, limiting inference about timing or conviction. Notably, Cieri retains 154,770 restricted stock units, meaning his overall equity exposure at BILL remains material despite the substantial reduction in non-derivative holdings.

Director Brian Jacobs buys 25,000 BILL shares across 2 trades for $1,338,396.50; +548.4% increase in holdings amid cluster buying pattern.

Director Brian Jacobs purchased 25,000 shares of BILL Holdings in 2 separate transactions on 2024-08-27 and 2024-08-28 at blended average price of $53.54, bringing his total holdings from 4,559 shares to 29,559 shares. This represents a substantial 548.4% increase in his personal stake at a price point $1.23 above the current market price of $52.31, indicating the purchases occurred before recent stock decline. The transactions occur within a cluster pattern where 2 other insiders also bought within the past 14 days, which may signal broader internal conviction about the company's prospects. Against this context, BILL trades 55.7% below its 52-week high of $118.20, though the company reports strong fundamentals including $323,028,000.00 quarterly revenue with +21.9% annual growth and $31,809,000.00 quarterly net income.

CFO Rettig buys 21,124 shares at $49.40 average; stock down 57.9% from 52-week high, holdings up 35.6%

John R. Rettig, CFO of BILL Holdings, executed 3 separate purchases totaling 21,124 shares for $1,043,481.36 on 2024-08-26, raising his holdings from 59,350 to 80,474 shares (+35.6%). The blended transaction price was $49.40, occurring while the stock trades at $49.77 (current), down 57.9% from its 52-week high of $118.20 and down 5.8% over the prior 30 days. At the fundamental level, the company reported $323.0M in latest-quarter revenue (+21.9% annual growth) and $31.8M net income, but full-year results were unprofitable. The timing of this buy coincides with depressed valuation relative to recent history, though his prior 5 trades at BILL were all sells (100% of prior same-ticker history), each well-timed at the 90-day mark. This buy represents a notable reversal from that historical pattern and a material increase in personal exposure at a price level substantially below recent highs.

CEO Lacerte bought 42,248 shares at $49.60 avg for $2.1M, growing stake 29.8%; stock -57.9% from 52-week high

Lacerte Rene A., CEO of BILL Holdings, executed 4 separate open-market purchases totaling 42,248 shares (42.2K shares) for $2,095,349.16 ($2.1M) on 2024-08-26 at a blended average price of $49.60, increasing his holdings by 29.8% from 142,001 to 184,249 shares. The timing coincides with material stock weakness: BILL has declined 57.9% from its 52-week high of $118.20, trading at $49.77 (near the purchase price). His prior trading history at this ticker shows all 5 recent sales were well-timed at the 90-day mark—each preceded material declines, suggesting pattern recognition of downturns. The company's fundamentals remain operationally solid (revenue $323.0M, up 21.9% year-over-year, with $31.8M net income in the latest quarter), yet full-year results turned negative, and the valuation (P/E 37.14, market cap $5.3B) reflects investor skepticism. This large open-market accumulation by the CEO at depressed levels, combined with his demonstrated ability to navigate prior cycles at this ticker, warrants investor scrutiny of his intent and confidence signal at current valuations.