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BOX BOX INC Insider Trading

Latest: CFO Sold $592K of Shares · May 2026

Multiple insiders have been active at BOX INC (BOX): 4 distinct insiders account for 0 buy filings and 10 sell filings as of May 2026. Its highest-significance filing in the last 90 days: CFO Smith Dylan C sold $592K, transaction dated May 2026.

10 filings analyzed · Latest 2026-05-11

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Buys
0
Sells
10
Insiders
4
Direction
Net selling

BOX INC leadership

CEO
Aaron Levie — CHIEF EXECUTIVE OFFICER
CFO
Dylan Smith — CHIEF FINANCIAL OFFICER
General Counsel
David Leeb — Chief Legal Officer and Corporate Secretary
Chair
Bethany Mayer — Chair

Historically, stocks have lagged the S&P 500 by a median ~3% over the 90 days after a medium insider sell (n ≈ 4,738, 2024-2026). Past results don't predict the future. How we measure this ↗

May 2026
2026-05-11 10b5-1 Plan
medium
Chief Financial Officer
23,720 shares
$592,094
@ $24.96
Significance 4

CFO Smith Dylan C sold ~23,700 shares for $592K, adding to five straight years of steady dispositions at this company.

Dylan Smith, BOX's Chief Financial Officer, sold nearly 24,000 shares across two transactions on the same day, marking his 35th open-market sale in the trailing 36-month window. This is not an anomaly—Smith has sold exclusively at BOX for the past five years with no offsetting open-market purchases. His prior four sales at this company saw the stock decline in the months that followed, though his most recent sale in early January was followed by a modest near-term dip before a rebound, making his timing mixed when viewed across different horizons. The stock currently trades well below its 52-week high, down significantly from recent peaks, yet Smith continues to reduce his stake. BOX remains profitable with solid revenue growth, suggesting this disposition is driven by portfolio management rather than operational distress, but the unbroken sell-only pattern over multiple years merits scrutiny of whether the CFO holds conviction in the company's direction or is simply executing a systematic divestment plan.

April 2026
2026-04-08
medium
VP Chief Acct Ofr & Controller
24,500 shares
$584,300
@ $23.85
Significance 5

VP Chief Acct Officer Berkovitch sells 24.5K BOX shares at $23.85; holds 95.5K post-sale as stock down -39.9% from 52-week high

Berkovitch, VP Chief Accounting Officer and Controller, executed a sale of 24,500 shares on 2026-04-08 for $584,300.50, reducing his holdings from 120,016 to 95,516 shares—a -20.4% reduction in his position. The transaction occurred at $23.85 per share while the stock trades at $23.18 today, down -39.9% from its 52-week high of $38.55 and -21.6% over the past 90 days. As the senior accounting executive, any material position reduction warrants attention for potential underlying concerns, though the fundamental picture shows modest growth (annual revenue growth +8.0%, P/E of 32.65) alongside a $12.1M net income on $301.1M revenue. Investors should monitor whether this single officer's disposition foreshadows broader sentiment shifts, particularly given the sharp 52-week drawdown.

January 2026
2026-01-12 10b5-1 Plan
low
Chief Financial Officer
17,000 shares
$502,656
@ $29.57
Significance 3

CFO Dylan C Smith sold 17,000 BOX shares at $29.57 under pre-arranged 10b5-1 plan adopted 2025-05-29

Dylan C Smith, Chief Financial Officer of BOX INC, sold 17,000 shares on 2026-01-09 for a total value of $502,656.00, reducing his holdings from 1,345,195 shares to 1,328,195 shares. The sale was executed under a pre-arranged 10b5-1 trading plan adopted on 2025-05-29, meaning this was a scheduled transaction rather than a discretionary trade decision. The 1.3% reduction in his personal holdings is consistent with a programmatic divestiture schedule and does not reflect an ad-hoc market decision by the CFO.

December 2025
2025-12-12 10b5-1 Plan
medium
Chief Financial Officer
17,000 shares
$526,422
@ $30.97
Significance 5

BOX CFO Smith Dylan C sold 17,000 shares at $30.97 on 2025-12-10, retaining 1.42M shares; stock down 21.8% from 52-week high.

Smith Dylan C, as CFO, executed an open-market sale of 17,000 shares valued at $526,422.00, reducing his holdings by 1.2%. The sale occurred at $30.97, but BOX has declined to $30.13 (current) and sits -21.8% from the 52-week high of $38.55. His cross-ticker track record shows a 100.00% well-timed rate across 3 prior sells with an average 90-day return of -4.7%, indicating a pattern of selling ahead of declines. At BOX specifically, his prior sale on 2025-09-10 resulted in a -4.7% 90-day return, also well-timed. The current sale follows two prior sales at BOX within the last two months (2025-11-10 and 2025-10-10, both showing negative 30-day returns), suggesting a persistent pattern of liquidation during a downtrend. Box's fundamentals remain solid (P/E 18.95, $301.1M quarterly revenue, +5.0% annual growth), so the signal appears driven by the CFO's demonstrated selling behavior in deteriorating price conditions rather than fundamental deterioration.

November 2025
2025-11-13 10b5-1 Plan
low
Chief Financial Officer
17,000 shares
$533,154
@ $31.36
Significance 4

CFO Smith Dylan C sold 17,000 BOX shares at $31.36 on 2025-11-10 for $533,154.00

Smith Dylan C, the CFO, sold 17,000 shares representing a -1.2% reduction of his 1,454,013 pre-transaction holdings. The stock currently trades at $31.99, down 2.0% over the past 30 days and -17.0% from its 52-week high of $38.55, indicating a period of relative weakness. Reviewing his same-ticker history at BOX, his prior sale on 2025-10-10 was followed by a -5.1% 30-day return, while the 2025-09-10 sale saw a +0.3% 30-day return; neither outcome is yet measurable at the 90-day mark. Across his broader cross-ticker track record, two prior sells averaged a -2.4% 30-day return. The company's fundamentals show a P/E of 20.25 with annual revenue growth of +5.0% and quarterly revenue of $293,999,000.00, reflecting a moderately growing business on a reasonable valuation multiple. This represents a routine portfolio transaction in the context of holdings totaling 1.44M shares; the modest position reduction does not signal a material reassessment of the CFO's commitment to the company.

October 2025
2025-10-14 10b5-1 Plan
low
Chief Financial Officer
17,000 shares
$561,833
@ $33.05
Significance 4

CFO Smith Dylan C sold 17,000 BOX shares at $33.05; retains 1.45M shares post-transaction.

Smith Dylan C, Chief Financial Officer of Box Inc, sold 17,000 shares at $33.05 on 2025-10-10, reducing his holdings from 1.47M to 1.45M shares—a 1.2% reduction in his position. The sale occurred when the stock was trading at $33.05, which is -15.3% below the 52-week high of $38.55, and the current price of $32.65 remains near the transaction level. The CFO retains a substantial 1.45M share position, indicating ongoing material stake in the company. His cross-ticker track record shows only 1 prior open-market sell with a 30-day average return of +0.3%; at Box specifically, he has one measurable prior sale (2025-09-10) with a 30-day return of +0.3%. Fundamentals show Box reported quarterly revenue of $294.0M with annual growth of +5.0%, net income of $13.4M, and a P/E of 20.66 against a market cap of $4.7B—metrics that do not indicate distress.

September 2025
2025-09-11 10b5-1 Plan
low
Chief Financial Officer
51,000 shares
$1,674,432
@ $32.83
Significance 4

BOX CFO Dylan Smith sells 51,000 shares at $32.83 for $1.7M; retains 1.48M shares post-sale

Smith Dylan C, as CFO, sold 51,000 shares at $32.83 on 2025-09-10, a sale representing -3.3% of his pre-transaction holdings and reducing his position to 1,480,732 shares. The sale occurred at a price below the current market price of $33.00 and below the 52-week high of $38.55, reflecting modest downward distance from recent trading. BOX trades at a P/E of 20.89 with quarterly revenue of $293,999,000.00 and net income of $13,445,000.00; the company posted 5.0% annual revenue growth. The sale is a discrete, moderate-volume transaction that occurs within the context of the CFO maintaining a substantial remaining stake, providing limited directional signal about management sentiment.

July 2025
2025-07-14 10b5-1 Plan
low
Chief Executive Officer
15,000 shares
$500,220
@ $33.35
Significance 3

BOX CEO Aaron Levie sells 15,000 shares ($500.2K) at $33.35; retains 2.95M shares post-transaction.

CEO Aaron Levie sold 15,000 shares (15.0K shares) of BOX at $33.35 on 2025-07-10 for $500,220.00 ($500.2K), representing a -0.5% reduction in his 2.97M share position. At the current price of $32.55, the stock is trading 15.6% below its 52-week high of $38.55 and has declined 8.5% over the past 30 days, though it is up 8.7% over 90 days. With BOX trading at a P/E of 19.97 and the company posting modest revenue growth of 5.0% year-over-year on $276.3M quarterly revenue, this small-scale sale by the CEO does not represent a material reduction in his insider position and provides limited directional signal given the transaction's modest scale relative to his remaining holdings.

June 2025
2025-06-02
high
37,499 shares
$1,377,826
@ $36.74
Significance 7

Director Daniel Levin sells entire 37,499-share BOX position for $1.4M, completing 100% liquidation after pattern of well-timed exits

Daniel Levin completely exited his BOX position on 2025-05-29, selling all 37,499 shares at $36.74 for $1,377,825.76—eliminating his entire stake. This full liquidation follows a documented pattern: his prior 5 trades at BOX (all sales between March and December 2024) were each well-timed, with 100% achieving negative 90-day returns after the sale date. His cross-ticker track record across all open-market activity shows an even stronger 100.00% well-timed rate on 5 prior sells with an average 90-day return of -6.1%. The current price of $38.11 sits at the 52-week high (+0.0% from peak), suggesting the director completed this exit at a historically elevated level and before any visible downturn has materialized. The complete elimination of holdings—combined with the insider's consistent historical success in exiting BOX positions before subsequent declines—merits careful attention to forward catalysts.

December 2024
2024-12-12
high
187,498 shares
$6,138,116
@ $32.74
Significance 7

Director Daniel J Levin liquidates entire BOX position: 187,498 shares across 3 sales (Dec 10-12) for $6,138,116.41, exiting 100% of holdings.

Director Levin executed 3 separate sales over 3 trading days (December 10–12, 2024), disposing of his complete 187,498-share stake at an average price of $32.74. This represents a complete liquidation of his position at BOX, with the current price now at $33.02. Notably, Levin's prior two sales at BOX (March 2024) both achieved 90-day negative returns of -10.2% and -9.9%, a pattern consistent with his cross-ticker track record showing a 100.00% well-timed sell rate across 2 prior open-market sales. The full exit of his shareholding, combined with his demonstrated history of selling ahead of subsequent stock declines at this ticker, warrants close attention to whether this signals a material shift in company prospects or senior leadership confidence.

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