DUOL Duolingo, Inc. Insider Trading

Director Shelton James H purchased 5,000 DUOL shares at $99.76 on 2026-03-03, increasing holdings 107.9%; stock now -82.2% from 52-week high.

Director Shelton James H purchased 5,000 shares of Duolingo at $99.76 on 2026-03-03, doubling his position from 4,632 shares to 9,632 shares. The transaction occurs within a steep drawdown: the stock trades at $96.17, down -27.1% in 30 days and -49.0% in 90 days, standing -82.2% below its 52-week high of $540.68. At the same ticker, his 5 prior trades (all sales) posted positive 90-day returns averaging between 24.3% and 59.2%, with none well-timed on the downside—a pattern of selling before rallies rather than before declines. The company maintains strong fundamentals: $271.7M quarterly revenue, $292.2M net income, 38.7% annual revenue growth, and a historically low P/E of 2.25, though whether this valuation reflects genuine opportunity or structural concerns requires deeper examination. The buy occurs amid substantial price weakness after extended losses, without indicators from prior cross-ticker activity that this director has successfully timed market troughs.

CFO Skaruppa sells 5,856 DUOL shares for $658,304.07 across 5 transactions; stock down 79.1% from 52-week high.

Matthew Skaruppa, CFO of Duolingo, executed 5 separate sales totaling 5,856 shares for $658,304.07 between February 17–18, 2026, at prices ranging from $110.06 to $115.29, reducing his holdings by 15.6% to 31,631 shares. The timing is noteworthy: prior to this filing, his 5 same-ticker sells at DUOL were all well-timed at the 90-day mark (each showing 90-day returns between -35.3% and -36.6%), and the stock has since declined 79.1% from its 52-week high of $540.68, trading at $112.94 currently and down 23.1% over the past 30 days. Despite strong fundamentals—revenue growth of 40.8%, net income of $292.2M, and a low P/E of 4.87—the sharp valuation reset and the CFO's consistent pattern of well-timed sales suggest insider awareness of deteriorating market conditions or mean-reversion pressures at these price levels.

CTO Hacker Severin sells 10,000 DUOL shares for $1.7M via 8 transactions; stock down 47.1% in 30 days

Hacker Severin, Chief Technology Officer and Co-Founder, executed 8 separate sales on 2025-11-19 totaling 10,000 shares for $1,727,441.09, reducing his position from 10,072 shares to 72 shares post-transaction. The blended average sale price of $172.74 contrasts sharply against the current price of $168.01 and a 52-week high of $540.68, indicating the stock has declined 68.9% from its peak and 47.1% over the past 30 days. Severin's cross-ticker track record shows 20 prior sells averaging -44.5% return over 30 days, though his prior same-ticker activity at DUOL (5 recent sales on 2025-11-04) does not yet have measurable outcomes. The filing contains a derivative-conversion component, meaning his actual residual position extends beyond the 72 shares reflected in Table I.

CFO Skaruppa sells 5,858 shares for $1.0M across 6 transactions; stock down 44.2% in 30 days, 49.5% in 90 days from $540.68 peak

Matthew Skaruppa (CFO) executed 6 separate sales totaling 5,858 shares for $1,035,724.76 across November 17–18, 2025, at prices ranging from $174.04 to $177.95, leaving him with 37,487 shares post-transaction (a 13.5% reduction from 43,345 shares). The timing is notable: the stock has fallen 67.7% from its 52-week high of $540.68 to the current $174.48, with particularly sharp declines over the 30-day (-44.2%) and 90-day (-49.5%) windows preceding this filing. This sell occurred as the company posts strong fundamentals—40.8% annual revenue growth, profitability of $292.2M net income on $271.7M quarterly revenue, and a P/E of 7.52—suggesting the selloff is driven by market dynamics rather than company performance. Skaruppa's cross-ticker track record shows 80% well-timed sells (20 prior transactions) with an average 90-day return of -26.4%, but his same-ticker history at DUOL (5 prior sells in August 2025) had mixed 30-day outcomes and no measurable 90-day results, offering limited precedent for assessing this round's execution.

CTO Hacker Severin sells 10,000 shares ($2.6M) at $263.13 avg; stock now -64.2% from 52-week high

On 2025-11-04, Hacker Severin, Chief Tech Officer and Co-Founder of Duolingo, filed a Form 4 reporting 10 separate sales totaling 10,000 shares for $2,631,299.19 at prices ranging from $257.92 to $266.12, with a blended average of $263.13. This represents a sale of 99.3% of his pre-transaction holdings, leaving only 72 shares post-trade. The timing is material: the stock is currently trading at $193.74, down 64.2% from its 52-week high of $540.68 and down 39.4% over the preceding 30 days. His cross-ticker historical track record shows an average 30-day return of -18.8% following prior sales, and he executed five prior sales at DUOL on 2025-10-20 (outcomes not yet measurable). The large concentrated sale by a co-founder and CTO at elevated prices, followed by a sharp reversal in stock price, raises questions about information asymmetry and timing, particularly given the recent prior sales at this same ticker and the company's strong fundamentals (annual revenue growth of 40.8%, P/E of 8.35).

CTO Hacker Severin sold 10,000 DUOL shares for $3.1M on 2025-10-20; 99.3% position reduction to 72 shares

Hacker Severin (Chief Tech Officer, Co-Founder) executed 15 separate sales totaling 10,000 shares for $3,147,198.32 on 2025-10-20, reducing his holdings from 10,072 shares to 72 shares—a 99.3% reduction. The sales occurred across a range of prices from $305.86 to $324.10, with a blended average of $314.72. This represents a near-complete liquidation of his open-market position, though derivative holdings in Form 4 Table II may represent additional exposure not yet populated in our database. The transaction occurred as DUOL trades 43.1% below its 52-week high of $540.68 and 90 days after recent sales on 2025-10-06 (outcomes not yet measurable). His cross-ticker track record shows 20 prior sells with an average 30-day return of +15.9%, indicating historical ability to time sales, though this metric does not extend to his same-ticker history at DUOL.

CTO Hacker Severin sold 10,000 shares (10.0K shares) for $3.2M at blended $321.63, leaving 72 shares held. Derivative conversion flagged.

Hacker Severin, Chief Technology Officer and Co-Founder, executed 11 separate sales totaling 10,000 shares for $3,216,303.32 on 2025-10-06 at prices ranging from $317.31 to $328.76. The filing contains a derivative-conversion notation, indicating the disposition involves conversion of derivative securities; the insider's full position exposure (including any remaining derivative holdings) is not fully reflected in the Table I share count of 72 shares post-transaction. This transaction reduced his direct shareholding by 99.3% relative to pre-transaction holdings of 10,072 shares. The company trades at a P/E of 45.45 with revenue growth of 40.8% year-over-year, and the stock has declined 40.8% from its 52-week high of $540.68 despite a 30-day gain of 18.0%. His cross-ticker track record across 20 prior open-market sales shows a 2.6% average 30-day return, though prior same-ticker outcomes at DUOL remain immeasurable. Investors should monitor the derivative holdings disclosure when fully populated to assess the true scope of position change.

Chief Engineering Officer Natalie Glance sells 3,283 shares at blended $312.30 on 2025-10-01 for $1.0M; stock currently $320.31.

Natalie Glance, Chief Engineering Officer at Duolingo, executed 9 separate sales totaling 3,283 shares for $1,025,265.12 on 2025-10-01 at prices ranging from $300.56 to $319.76, reducing her holdings by 2.7% to 116,171 shares. Her same-ticker history at DUOL shows 5 prior sales on 2025-07-01, all achieving negative 90-day returns (-12.5% to -19.4%), with a perfect 5-of-5 well-timed pattern at the 90-day mark. Her broader cross-ticker track record spans 20 prior sells with a 90.00% well-timed rate and -20.7% average 90-day return, indicating a persistent pattern of selling ahead of declines. The current stock price of $320.31 is 40.8% below its 52-week high and has risen 18.1% over 30 days, yet remains down 17.8% over 90 days—positioning consistent with her demonstrated pattern. The company's fundamentals remain strong: $252.3M quarterly revenue with 40.8% annual growth, $44.8M net income, and a $5.3B market cap, but the timing of this sale aligns with her established track record of sales preceding downward price movement.

CTO Hacker Severin sold 10,000 shares of DUOL for $2.9M on 2025-09-19, reducing stake from 10.1K to 72 shares.

Hacker Severin, Chief Technology Officer and Co-Founder of Duolingo, executed 5 separate sales totaling 10,000 shares for $2,889,373.13 at prices ranging from $286.77 to $290.78, leaving only 72 shares post-transaction. This represents a reduction of -99.3% vs pre-transaction holdings, though per the derivative-conversion flag, this filing reflects conversion of derivative securities and the Table I shares_after figure (72 shares) may not represent the insider's total position across derivative and equity holdings combined. The transactions occurred on 2025-09-19 when DUOL was trading near $309.34 current price; the stock has declined -26.8% over the prior 90 days and -6.8% over the trailing 30 days, trading -42.8% below its 52-week high of $540.68. Severin's cross-ticker track record spans 20 prior sells with an average 90-day return of -17.2%, while his prior sales at DUOL on 2025-09-05 (4 transactions) remain too recent to measure outcomes. The company's fundamentals show strong revenue growth of +40.8% annually and a P/E of 43.94, though the stock's recent weakness and Severin's near-complete open-market liquidation merit investor scrutiny given his founder-level influence on product and strategy.

Duolingo CTO Hacker Severin sold 10,000 shares for $2.7M in 8 transactions on 2025-09-05; retains 72 shares post-transaction.

Hacker Severin, Chief Tech Officer and Co-Founder, executed 8 separate sales totaling 10,000 shares for $2,685,461.75 at a blended average price of $268.55 on 2025-09-05. This represents a -99.3% reduction of his pre-transaction holdings, leaving him with only 72 shares. The timing is notable: Severin's prior 20 open-market sells across all tickers averaged a 30-day return of -20.4%, and DUOL shares have declined -26.2% over the past 30 days and -42.3% over 90 days from a 52-week high of $540.68. At DUOL specifically, he conducted 5 prior sells on 2025-08-19 (outcomes not yet measurable), suggesting recent sustained selling activity at the company. The company fundamentals remain relatively strong (revenue $252.3M, net income $44.8M, annual growth +40.8%, P/E 38.85), but the magnitude and concentrated timing of this near-total reduction in his position, combined with his cross-ticker sell history averaging negative 30-day returns, may warrant investor attention to any broader context around the sale.