Upwork’s second quarter was marked by ongoing challenges tied to the accelerating adoption of artificial intelligence (AI) and changing patterns in client acquisition. Management emphasized that increased AI automation, especially for lower-complexity work, and headwinds from shifting Google Search dynamics weighed on active client numbers. CEO Hayden Brown described the environment as “a transition of work broadly,” noting the impact of rapid AI-related automation and a deterioration in search-driven customer acquisition. Upwork’s efforts to pivot toward higher-value, more complex projects and to strengthen its enterprise and AI-related offerings were highlighted as key responses to these pressures.

Upwork (UPWK) Q2 CY2026 Highlights:

• Revenue: $191.7 million vs analyst estimates of $190 million (1.7% year-on-year decline, 0.9% beat)
• Adjusted EPS: $0.41 vs analyst estimates of $0.34 (19.7% beat)
• Adjusted EBITDA: $64.05 million vs analyst estimates of $57.61 million (33.4% margin, 11.2% beat)
• The company dropped its revenue guidance for the full year to $740 million at the midpoint from $775 million, a 4.5% decrease
• Management lowered its full-year Adjusted EPS guidance to $1.40 at the midpoint, a 7.9% decrease
• EBITDA guidance for the full year is $230 million at the midpoint, below analyst estimates of $254.4 million
• Operating Margin: 14.7%, down from 16.7% in the same quarter last year
• Market Capitalization: $1.06 billion

While we enjoy listening to the management’s commentary, our favorite part of earnings calls is the analyst questions. Those are unscripted and can often highlight topics that management teams would rather avoid or topics where the answer is complicated. Here is what has caught our attention.

Our Top 5 Analyst Questions From Upwork’s Q2 Earnings Call

• Ronald Josey (Citi): Asked about the visibility on operating challenges and the impact of SEO changes. CEO Hayden Brown explained that the environment remains volatile as AI automation and search headwinds persist, but highlighted ongoing marketing and product pivots to address these issues.
• Eric Sheridan (Goldman Sachs): Queried about the expected duration of the AI-driven transition and the evolution of the active client base. Brown stated it is difficult to predict the timeline but emphasized Upwork’s focus on serving higher-value, AI-driven work across all client segments.
• Bernard McTernan (Needham & Company): Questioned the slowdown in AI category growth and the drivers of the take rate. Brown noted the undercounting of AI work due to changing client behavior and highlighted dynamic pricing and monetization initiatives as contributors to take rate expansion.
• Sang-Jin Byun (Jefferies): Inquired about the progress of the Lifted enterprise migration and pipeline health. Brown pointed to positive feedback, successful migrations, and the closing of significant enterprise contracts as evidence of traction.
• Matthew Condon (Citizens JMP): Sought clarity on enterprise exposure to AI and the effectiveness of new acquisition channels. Brown described diversification across work types and increased spend in underpenetrated paid channels like international SEM, Meta, and connected TV.

Catalysts in Upcoming Quarters

In the coming quarters, the StockStory team will be monitoring (1) the pace and effectiveness of paid acquisition investments to offset search-related headwinds, (2) client adoption and monetization of new AI-integrated features like the MCP server, and (3) the ongoing success of Lifted and Business Plus in driving higher-value, recurring enterprise engagement. The evolution of AI-related work and stabilization in marketing channels will also be central to tracking Upwork’s progress.

Upwork currently trades at $8.55, down from $9.83 just before the earnings. At this price, is it a buy or sell? See for yourself in our full research report (it’s free).