Oberndorf Exits Entire Stake in monday.com
monday.com shares rose by 10.02% and reached a 20-day high amid mixed market performance.
The fund controlled by William Oberndorf sold all 73,705 shares of monday.com in Q1 2026, valued at $7.07 million, marking a complete exit. This transaction resulted in a net position value drop of $10.88 million, reflecting not only the impact of the share sale but also price movements, indicating pressure on the fund in the current market environment. The sale occurred amid a broad sell-off, suggesting a loss of confidence in the company while simultaneously seeking other investment opportunities.
This exit may raise concerns among investors regarding monday.com's competitive position in the SaaS sector, especially given its significant underperformance compared to the S&P 500.
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- Significant Revenue Growth: In 2025, monday.com achieved a 26% year-on-year revenue increase in the EMEA region, reflecting strong performance and sustained customer demand, which further solidifies its position in the global market.
- Leadership Change: Ben Barnett has been appointed as General Manager for EMEA, tasked with driving the company's go-to-market strategy and key partnerships, which is expected to accelerate monday.com's expansion in the AI work platform space and enhance customer experience and market competitiveness.
- Regional Expansion: monday.com has expanded its EMEA headquarters in London to 80,000 square feet, now housing over 370 employees, while also adding offices in Paris and Munich, demonstrating the company's commitment and investment in the region.
- Product Transformation: The company has completed its most significant product overhaul in history, transitioning from a work management solution to a unified AI work platform, aimed at enhancing work efficiency through automation and intelligence to meet the growing demands of customers.
- Full Exit: The fund controlled by William Oberndorf sold all 73,705 shares of monday.com in Q1 2026, valued at $7.07 million, marking a complete exit, with monday.com now representing 0% of the fund's reportable AUM.
- AUM Decline: This transaction resulted in a net position value drop of $10.88 million, reflecting not only the impact of the share sale but also price movements, indicating pressure on the fund in the current market environment.
- Poor Market Performance: As of May 13, 2026, monday.com shares were priced at $67.70, down 76.7% over the past year, significantly underperforming the S&P 500 by 103.16 percentage points, suggesting a weakening competitive position in the SaaS sector.
- Investor Confidence Erosion: Oberndorf's fund completely liquidated its stake in monday.com amid a broad sell-off, indicating a loss of confidence in the company while simultaneously seeking other investment opportunities, as evidenced by a 52% increase in its stake in Veeva Systems.
- Leadership Transition: Drew Houston, the founder and CEO of Dropbox, is transitioning to an executive chairman role while sharing CEO duties with Ashraf Alkarmi, who is being promoted from product chief, indicating a significant shift in leadership aimed at enhancing innovation and market responsiveness.
- Stable User Base: Dropbox boasts over 18 million paying users, maintaining a strong market position among media and design professionals despite fierce competition from Google and Apple, demonstrating the enduring appeal of its services.
- Stagnant Revenue Growth: Although Dropbox surpassed $2 billion in annual revenue in 2021, its revenue has remained flat over the past two years, reflecting challenges in a competitive landscape and the rapid evolution of the AI sector.
- AI Opportunities: Dropbox is leveraging AI technology to enhance user experience with the launch of its AI-powered Dash feature, which aids users in efficiently searching and interacting with documents, and analysts believe this could attract value investors despite pressures from emerging technologies.
- Leadership Transition: Drew Houston, founder and CEO of Dropbox, is stepping down to become executive chairman, with Ashraf Alkarmi promoted to co-CEO, indicating a significant shift in leadership that may influence the company's strategic direction moving forward.
- Market Performance Decline: Dropbox's current market cap is just over $6 billion, down by half from its peak on the first day of trading in 2018, reflecting the challenges the company faces in the highly competitive cloud storage market, particularly against giants like Google and Apple.
- Stable User Base: Despite competition, Dropbox boasts over 18 million paying users and remains popular among media professionals and designers, demonstrating its sustained appeal in specific market segments.
- AI Opportunities and Challenges: Dropbox is leveraging AI technology to enhance user experience with its AI-powered Dash feature, and while overall revenue has remained flat over the past two years, analysts believe the AI opportunity could attract value investors' interest.
- Share Sale Overview: ShawSpring exited 253,959 shares of monday.com last quarter, with an estimated trade value of $24.37 million, reflecting a diminished confidence in the company as this transaction represented 9.1% of its assets under management.
- Position Value Decline: The quarter-end position value for ShawSpring in monday.com decreased by $37.47 million, a change driven not only by the share sale but also by price fluctuations, indicating a prevailing pessimism in the market regarding the company's prospects.
- Company Performance Highlights: Despite the significant drop in stock price, monday.com reported a 24% year-over-year revenue increase to $351.3 million in Q1, with GAAP operating income doubling to $19.8 million, suggesting strong fundamentals and the new AI Work Platform as a key growth driver.
- Repurchase Plan Implementation: monday.com authorized a stock repurchase plan of approximately $553 million during the quarter, demonstrating management's confidence in the company's future growth, even as it navigates intense competition in the work management and AI software sectors.
- Position Liquidation: On May 14, 2026, ShawSpring Partners disclosed in an SEC filing that it sold its entire position of 253,959 shares in monday.com, with an estimated transaction value of $24.37 million, indicating a lack of confidence in the stock's future performance.
- Market Value Decline: This transaction resulted in a $37.47 million decrease in monday.com's quarter-end position value, reflecting a staggering 73% drop in share price over the past year, significantly underperforming the S&P 500's 28% gain.
- Performance Highlights: Despite the sharp decline in stock price, monday.com reported a 24% year-over-year revenue increase to $351.3 million in Q1, with GAAP operating income doubling to $19.8 million, demonstrating strong underlying business fundamentals.
- Customer Growth: The number of customers generating over $100,000 in annual recurring revenue surged by 39%, while those contributing over $500,000 jumped 74%, indicating healthy market demand, alongside management's authorization of a $553 million share repurchase program.











