Skaruppa Matthew

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.

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.

DUOL CFO sells 10,937 shares for $3.5M on 2025-08-26; 4 of 4 prior sales at this ticker well-timed at 90-day mark

Matthew Skaruppa, CFO of Duolingo, executed 10 separate sales totaling 10,937 shares for $3,471,321.56 on 2025-08-26, reducing his holdings by 20.1% from 54,282 to 43,345 shares at a blended average price of $317.39. The stock currently trades at $322.78, down 40.3% from its 52-week high of $540.68 and down 37.9% over the past 90 days. Prior trading history at this ticker shows a strong timing pattern: all 4 measurable prior sales (2025-05-16 and 2025-08-15) resulted in negative 90-day returns ranging from -37.3% to -37.8%, with the insider's well-timed rate at 100% on this ticker. Given that the stock has declined 37.9% in the 90 days following this transaction window, the sale aligns with the insider's demonstrated ability to sell before declines at DUOL specifically.

CFO Matthew Skaruppa sold 2,797 shares of DUOL at $329.03 on 2025-08-15; stock now down 31.7% from 52-week high; 5 of 5 prior DUOL sales by Skaruppa were well-timed at the 90-day mark.

Skaruppa sold 2,797 shares at $329.03, reducing his holdings by -5.0%, while DUOL has declined 29.8% over 90 days and now sits 31.7% below its 52-week high of $540.68. His timing track record at this ticker is noteworthy: all 5 prior sales at DUOL were well-timed at the 90-day mark, with negative 90-day returns ranging from -37.3% to -37.9%, indicating he has consistently sold ahead of downturns. This filing does not reveal transaction-specific timing context (no FLAGS indicating scheduled 10b5-1 trading or other constraints), so the pattern of prior well-timed sells at DUOL remains a material observation for investors assessing whether this sale may signal further deterioration ahead. The company's fundamentals remain strong—$252.3M quarterly revenue with +40.8% annual growth and $44.8M net income—but the stock's recent sharp decline and the insider's demonstrated ability to exit ahead of weakness warrant monitoring.

CFO Skaruppa sold 3,573 shares at $528.35 avg for $1.9M on 2025-05-16, reducing holdings by 5.8%.

CFO Matthew Skaruppa executed 6 separate sales totaling 3,573 shares for $1,887,802.29 at a blended average price of $528.35, reducing his post-transaction holdings to 58,223 shares. This represents a 5.8% reduction from his pre-transaction holdings of 61,796 shares. The transaction occurred near the 52-week high of $540.68 and the stock now trades at $520.23, suggesting the sales occurred at elevated valuation levels. Notably, Skaruppa's prior sells at Duol all showed negative 30-day returns (ranging from -28.3% to -28.8% for the February 2025 batch), indicating his prior exit timing at this ticker has consistently preceded price declines. His cross-ticker track record across 20 prior sells shows an average 30-day return of +3.5% and 0% well-timed rate, reflecting that his sales have generally been followed by stock appreciation rather than decline.

CFO Skaruppa sells 3,304 DUOL shares for $1.8M at $531.71; stock near 52-week highs, down 2.2% from peak.

Matthew Skaruppa, CFO of Duolingo, sold 3,304 shares for $1,756,769.84 at $531.71 on 2025-05-15, reducing his stake from 65,100 to 61,796 shares (-5.1%). The sale occurred near the 52-week high of $540.68, with the stock currently at $529.05 and up 62.1% over the prior 30 days and 22.3% over 90 days. Across his cross-ticker open-market history, Skaruppa's prior 20 sells averaged -0.7% 30-day returns and +5.3% 90-day returns, with a well-timed rate of 0.00%, suggesting his historical sales have not preceded declines. Duolingo's fundamentals show strong momentum: +40.8% annual revenue growth, $230.7M latest-quarter revenue, and $35.1M net income, though the P/E ratio of 91.06 reflects elevated valuation expectations.

CFO Matthew Skaruppa sells 3,591 shares at avg $433.01; holds 56,391 post-sale amid 43.7% YoY revenue growth

Matthew Skaruppa, CFO of Duolingo, executed 6 separate sales totaling 3,591 shares for $1,554,953.63 on 2025-02-19 at a blended average price of $433.01, reducing his holdings by -6.0% to 56,391 shares. The current stock price of $385.35 now sits -12.7% from the 52-week high of $441.39 where the CFO was selling, yet the stock has appreciated +14.7% over the prior 30 days and +9.5% over 90 days. Duolingo's fundamentals remain robust with revenue of $192,594,000.00 in the latest quarter, net income of $23,360,000.00, and annual revenue growth of +43.7%, though the stock trades at an elevated P/E of 73.96. His prior same-ticker sales on 2025-01-13 and 2025-02-18 showed 30-day returns ranging +27.1% to +29.5%, indicating the stock rallied significantly after those sales. The disposition of this sale cannot yet be assessed on longer timelines, but the rapid succession of three sales within a month during strong price momentum warrants observation alongside the company's premium valuation.

CFO Matthew Skaruppa sold 3,284 DUOL shares at $435.28 on 2025-02-18, reducing holdings by 5.2% to 60.0K shares

Matthew Skaruppa, Chief Financial Officer of Duolingo, executed an open-market sale of 3,284 shares at $435.28, near the stock's 52-week high of $441.39. The transaction reduced his holdings from 63.3K to 60.0K shares, a 5.2% reduction. At the transaction price, DUOL was trading at a P/E of 80.96 against a market cap of $7.0B supported by $192.6M in latest-quarter revenue and $23.4M in net income. Skaruppa's cross-ticker track record shows 20 prior open-market sales with an average 90-day return of +20.8%, suggesting his historical sells have often preceded price appreciation rather than declines. However, his five prior trades at DUOL itself (all sales on 2025-02-19, one day after this filing date) lack measurable outcomes. The sale occurs in a stock that is +25.0% over the past 30 days and +19.8% over 90 days, and which is currently -4.4% from its 52-week high.

CFO Matthew Skaruppa sold 4,464 shares of DUOL for $1,399,697.76 in 8 separate transactions on 2025-01-13

CFO Matthew Skaruppa executed 8 separate sales totaling 4,464 shares for $1,399,697.76 at prices ranging from $307.48 to $316.59, reducing his holdings by 6.6% to 63,266 shares post-transaction. The sales occurred as DUOL trades at $312.52, down 7.6% over 30 days and down 16.2% from its 52-week high of $373.03, despite the company's strong fundamentals including +43.7% annual revenue growth and $192.6M quarterly revenue. Notably, Skaruppa executed similar sales just 11 days prior on 2025-01-02 (4 transactions documented in SAME-TICKER HISTORY with outcomes not yet measurable), signaling a pattern of discretionary selling activity within a compressed timeframe. His cross-ticker track record shows 20 prior sells with an average 30-day return of -5.9%, and none of those prior sales achieved well-timed outcomes at the 90-day mark, though this stock's recent price momentum provides limited context for assessing outcome patterns yet.

CFO Skaruppa sells 5,000 DUOL shares for $1.6M across 6 transactions on 2025-01-02 at $321.46–$328.53

Matthew Skaruppa, CFO of Duolingo, executed 6 separate sales totaling 5,000 shares for $1,622,407.91 on 2025-01-02, reducing his holdings from 72.7K to 67.7K shares (-6.9%). The blended average price of $324.48 sits between the 52-week range of $158.85–$373.03, and current price is $340.06 (8.8% above the transaction prices). His cross-ticker track record shows 20 prior sells with an average 30-day return of -3.1%, though outcome tracking at Duolingo specifically is not yet measurable on the 5 most recent trades at this ticker, all from 2024-12-16. Against the company's strong growth (revenue +43.7% annually, P/E of 65.27, market cap $5.7B), a mid-sized reduction in a senior executive's stake warrants standard investor monitoring but does not present anomalous timing or scale relative to his position size.