DBX DROPBOX, INC. Insider Trading

Co-CEO Ashraf Alkarmi sold 22,700 DBX shares at $27.86 on 2026-06-02 for $632,496.91; retains 1,080,746 shares post-sale.

Alkarmi's sale of 22,700 shares (-2.1% of pre-transaction holdings) reduced his position to 1,080,746 shares, representing a modest liquidation that does not suggest abandonment of the company. The transaction price of $27.86 is slightly above the current price of $27.59 and within the 52-week range of $21.70–$32.40; the current price sits 14.8% below the 52-week high, reflecting recent price weakness. Given the company's solid net income of $114,500,000.00 on revenue of $629,500,000.00 and a reasonable P/E of 14.60, the fundamentals do not immediately signal distress, though annual revenue growth of -1.1% reflects modest contraction. The sale scale and retained insider holdings suggest routine portfolio management rather than a large-scale departure or liquidation pattern.

CEO Houston Andrew sells 30.3K DBX shares at $27.50 via scheduled 10b5-1 plan; reduces holdings to zero.

Houston Andrew, Dropbox's Chief Executive Officer, executed a scheduled sale of 30,332 shares at $27.50 on 2026-05-18 via a pre-arranged 10b5-1 trading plan adopted on 2025-03-12, reducing his holdings to zero from 30.3K shares. The transaction was automatic and non-discretionary per the 10b5-1 framework, so it reflects a predetermined schedule rather than a tactical market timing decision. His cross-ticker track record shows 20 prior open-market sells with an average 90-day return of -4.8%, while his same-ticker history at DBX across 5 prior sales presents mixed outcomes: one recent sale on 2026-04-01 was followed by a 90-day gain of +17.2%, while three others faced 90-day losses ranging from -2.8% to -19.8%. The complete exit of all CEO holdings warrants disclosure attention, though the scheduled nature of the sale limits inference about current conviction.

CEO Houston Andrew sold all 37,498 DBX shares at $25.96 under 10b5-1 plan; current price $27.98.

Houston Andrew, Chief Executive Officer, sold all 37,498 shares of DROPBOX, INC. at $25.96 on 2026-05-14 under a pre-arranged 10b5-1 trading plan adopted on 2025-03-12, reducing his holdings to zero. The sale was scheduled rather than discretionary. At his prior trades at DBX, the 30-day and 90-day post-sale returns ranged from -11.2% to +17.2%, showing mixed outcomes; this particular transaction occurred near the 52-week high ($32.40), with current price at $27.98 representing -13.6% from that peak. The company reports net income of $114.5M on revenue of $629.5M for the latest quarter, with annual revenue growth of -1.1%.

CEO Houston Andrew sold 111.2K DBX shares ($2.5M) on 2026-04-01; stock down 10.6% in 30 days post-sale.

Houston Andrew, CEO of Dropbox, sold 111.2K shares at $22.89 on 2026-04-01 for total value of $2,544,600.86. The stock has declined 10.6% over the subsequent 30 days and is currently trading at $23.40, down 27.3% from its 52-week high of $32.17. His cross-ticker track record shows a 90-day well-timed rate of 68.75% across 20 prior sales, though at this same ticker DBX his measurable sell outcomes are mixed: the most recent prior 90-day outcome (2026-01-02 sale) registered a -15.2% return post-sale. The sale represents conversion of derivative securities (Form 4 Table II), not a complete portfolio exit. Fundamentals show net income of $123.8M against revenue of $634.4M with annual growth of -1.1%, and the stock trades at a 12.38 P/E multiple.

CEO Houston Andrew sold 109.5K DBX shares at $24.94 on 2026-03-02, totaling $2.7M; derivative conversion transaction.

Houston Andrew, CEO of Dropbox, sold 109,498 shares at $24.94 on 2026-03-02 in a derivative-conversion transaction. This sale represents conversion of derivative securities rather than a liquidation of his total position—Form 4 Table II (not yet populated in this database) contains his actual derivative holdings. In context of his same-ticker history, Andrew has executed five prior sales at DBX since January 2026, with 30-day outcomes ranging from -11.2% to +2.0%, indicating consistent equity reductions over recent weeks. His cross-ticker track record shows 20 prior sells with a 90-day well-timed rate of 66.67%, but measurable outcomes at this ticker are not yet available at the 90-day horizon. The stock is currently at $26.17, down 18.6% from its 52-week high of $32.17, and has gained 2.0% over the past 30 days. Dropbox fundamentals show stable profitability (net income $123.8M on revenue $634.4M latest quarter) and a moderate P/E of 13.85, though annual revenue declined 1.1% year-over-year.

CEO Houston Andrew sold 164,502 shares of DBX at $25.66 under pre-arranged 10b5-1 plan on 2026-02-02.

Houston Andrew, Chief Executive Officer, sold 164,502 shares of DROPBOX, INC. (DBX) at $25.66 for a total value of $4,221,088.42 on 2026-02-02 pursuant to a pre-arranged 10b5-1 trading plan adopted on 2025-03-12. This transaction is scheduled under the plan, not discretionary. The filing reflects a conversion of derivative securities; the insider's full position includes derivative holdings tracked in Form 4 Table II, which is not yet populated in this database, so the Table I post-transaction figure of 0 shares does not represent the insider's complete equity stake. The sale of 164,502 shares represents a specific execution under an established trading schedule rather than a discretionary portfolio decision.

DBX CEO Houston Andrew sold 60,000 shares for $1,651,456.40 in two transactions on Jan 9 & 12 at blended average $27.52

Chief Executive Officer Houston Andrew executed 2 separate sales totaling 60,000 shares for $1,651,456.40 at a blended average price of $27.52, reducing his holdings from 60,000 shares to 0 shares post-transaction. The sales occurred at prices ($27.54 and $27.51) above the current market price of $26.75, though the stock is down 5.5% over the past 30 days and 7.6% over 90 days. Notably, this filing contains a derivative-conversion transaction—the insider's actual position includes Form 4 Table II derivative securities not yet populated in our database, so the zero post-transaction Table I shares should not be interpreted as a complete position exit. Across his cross-ticker track record, the insider has achieved a 56.25% well-timed sell rate with an average 90-day return of -0.8% after sales; at DBX specifically, 1 of 1 measurable prior 90-day outcomes was well-timed, though recent same-ticker sales show mixed timing (30-day returns of -5.9% and -6.3% on recent December and November transactions).

CEO Houston Andrew sells 92,668 shares ($2.5M) via pre-arranged 10b5-1 plan on 2026-01-02

Houston Andrew, CEO of Dropbox Inc., executed 2 separate sales totaling 92,668 shares for $2,493,371.28 at blended average price of $26.91 on 2026-01-02. This transaction was executed under a pre-arranged 10b5-1 trading plan adopted on 2025-03-12, representing a scheduled disposition rather than a discretionary decision. The filing indicates derivative-conversion activity, meaning the CEO's actual equity position extends beyond the Table I shares shown in this filing; the shares sold represent a conversion of derivative securities, not necessarily a complete reduction of economic exposure. Investors should review the derivative holdings section when available to assess the insider's full economic position post-transaction.

CEO Houston Andrew sold 92,000 DBX shares at $29.53 (now $29.94) on 2025-12-01; holds derivatives only post-transaction.

On 2025-12-01, CEO Houston Andrew sold 92,000 shares of Dropbox for $2.7M at $29.53 per share. The shares are now trading at $29.94, a modest +0.8% gain over 30 days. Notably, this transaction was a derivative-conversion event, meaning the insider's true equity position continues through Table II derivative holdings (not yet visible in the structured data); the zero common-share holdings post-sale does not represent a full exit. At the broader level, Andrew's cross-ticker sell history shows 20 prior open-market sales averaging +3.2% returns over 30 days and +3.6% over 90 days, with 37.50% of those sales well-timed (i.e., followed by declines). At Dropbox specifically, the five prior sales show mixed 30-day outcomes (-4.0%, -2.1%, -1.6%, +4.7%, and outcomes pending on recent sales), with zero of one measurable sales well-timed at the 90-day horizon. The company's fundamentals show Revenue of $634.4M and Net income of $123.8M (latest quarter) with modest annual growth of +1.9% and a P/E of 21.08.

CEO Houston Andrew sold 101.2K shares of DBX at $30.23 (now $29.47); derivative-conversion trade, not full exit.

Houston Andrew, CEO of Dropbox, sold 101,167 shares at $30.23 on 2025-11-14, generating $3.1M in proceeds. This is a derivative-conversion transaction and does not represent a complete position exit; the insider's actual holdings in derivative securities (Form 4 Table II) are not yet populated in the database. Across his cross-ticker open-market history, Andrew's 20 prior sells averaged +3.2% 30-day and +4.7% 90-day returns, with a 37.50% well-timed rate, but at DBX specifically his prior 5 trades show mixed outcomes—including a -4.0% and -2.1% 30-day return on two sales just six weeks prior (2025-10-01). Stock fundamentals remain solid (revenue $634.4M, net income $123.8M, P/E 20.75), and the current price of $29.47 sits within the 52-week range and only 11.4% below the 52-week high, with modest positive momentum (30-day +1.2%, 90-day +3.7%). The trade warrants close observation of subsequent derivative-table disclosures and broader executive activity at DBX.