Investment Advisor Builds Massive Position in Upwork Stock with $6.8 Million Buy

On February 17, 2026, Ancient Art, L.P. disclosed a purchase of 372,147 shares of Upwork (UPWK +3.20%), an estimated $6.83 million trade based on quarterly average pricing.

What Happened

According to an SEC filing dated February 17, 2026, Ancient Art, L.P. increased its position in Upwork by 372,147 shares. The estimated transaction value was $6.83 million, based on the quarterly average share price from October 1 to December 31, 2025. The fund’s quarter-end Upwork position value increased by $12.71 million, reflecting both the share addition and stock price changes during the period.

What Else to Know

The buy lifted Upwork to 20.81% of Ancient Art, L.P.’s 13F assets under management as of December 31, 2025.

Top holdings after the filing:

• NASDAQ:IBKR: $105.70 million (23.9% of AUM)
• NASDAQ:UPWK: $91.98 million (20.8% of AUM)
• NASDAQ:SATS: $61.57 million (13.9% of AUM)
• NYSE:ALLY: $59.26 million (13.4% of AUM)
• NYSE:STLA: $38.11 million (8.6% of AUM)

As of February 17, 2026, shares were priced at $12.76, down 24.4% over the past year, underperforming the S&P 500 by 32.9 percentage points.

Company Overview

Company Snapshot

• Provides an online work marketplace connecting businesses with independent professionals and agencies across categories such as software development, design, marketing, and customer service.
• Generates revenue primarily through service fees charged to freelancers and clients for platform usage, as well as value-added offerings like Upwork Plus, Enterprise, Payroll, and managed services.
• Serves a global client base ranging from small businesses to large enterprises seeking flexible, remote talent solutions.

Upwork is a leading digital talent marketplace, facilitating remote work engagements between businesses and skilled professionals worldwide. The company leverages technology to streamline talent sourcing, contracting, and payment processes, positioning itself as a critical infrastructure provider for the evolving workforce. Upwork’s scalable platform and diversified service offerings underpin its competitive advantage in the online staffing industry.

What This Transaction Means for Investors

Ancient Art, a Texas-based investment advisor, recently disclosed the acquisition of more than 370,000 shares of Upwork, valued at around $6.8 million. Here’s what investors need to know about the transaction and Upwork stock.

First, we should note that Upwork’s stock has been on a rollercoaster ride. The company’s stock advanced by around 22% during calendar year 2025, enjoying a solid rally that saw it outperform the S&P 500. However, since New Year’s day, the stock has struggled. Year-to-date, shares have fallen by 35%.

What’s behind this volatility? In short, much of it comes down to artificial intelligence (AI). One could argue that Upwork is a company that both benefits from the rise of AI and is also pressured by it. To take the former first, Upwork is seeing a sizable uptick in AI-related work on its platform. This helps drive revenue and earnings higher, and it is clearly a strong catalyst for the stock. However, AI could also automate some other freelance tasks — tasks which have traditionally made up a substantial portion of Upwork’s marketplace. These AI substitution fears have gained traction in recent weeks, as disappointing revenue guidance from Upwork has led to the stock’s recent slide.

Therefore, this transaction comes at an interesting time for Upwork. Bulls and bears each have a case for why Upwork stock will either rebound or not. Given the size of its recent purchase, which makes Upwork its second-largest position, Ancient Art has faith that the company will bounce back. Retail investors who are skeptical of the AI substitution thesis may want to give Upwork stock a closer look.