Upwork Inc. (UPWK): A Bull Case Theory 

We came across a bullish thesis on Upwork Inc. on High Growth Investing’s Substack by Stefan Waldhauser. In this article, we will summarize the bulls’ thesis on UPWK. Upwork Inc.’s share was trading at $19.74 as of November 28th. UPWK’s trailing and forward P/E were 11.34 and 14.01 respectively according to Yahoo Finance.

Upwork Inc., together with its subsidiaries, operates a work marketplace that connects businesses with various independent professionals and agencies in the United States, India, the Philippines, and internationally. UPWK long observed from the sidelines, is re-emerging as a compelling platform investment after two challenging years marked by stagnating volumes and a “growth at all costs” strategy.

The marketplace has regained momentum, with monetization improving and cash flow turning decisively positive since 2023–24. Q3 2025 marked a major inflection point, delivering record revenue of ~$202 million, nearly $60 million in adjusted EBITDA (30% margin), and $69 million in free cash flow—more than the entire year of 2023. Gross Services Volume surpassed $1 billion again, signaling renewed platform vitality driven by 800,000 active corporate customers and 18 million freelancers.

Upwork’s network effects remain strong: predictable demand from businesses attracts talent, while enhanced digitalization ensures seamless contracting, compliance, and payments, supporting a steadily rising take rate of nearly 19% in the Marketplace segment. The company’s turnaround is closely tied to its female leadership duo—CEO Hayden Brown and CFO Erica Gessert—who have refocused Upwork on disciplined execution, stronger monetization, and AI-enabled product innovation. Their strategy has reshaped the cost base, improved profitability, and positioned Upwork to scale new opportunities.

The most significant strategic evolution is the expansion into enterprise budgets through the newly created subsidiary, Lifted, which finally enables Upwork to compete for large, complex contracts beyond traditional freelance placement. While Enterprise remains just under 15% of revenue today, its growth potential is substantial, especially with offerings like Business Plus bridging smaller companies and full enterprise services.

With $643 million in cash, minimal net debt, and a 2026 convertible note easily repayable from internal resources, Upwork now operates from a position of financial strength. Revenue growth is still modest at ~3% for 2025 due to seasonal Q4 softness, but acceleration is expected as GSV recovers and new enterprise channels scale. Altogether, Upwork’s renewed growth trajectory, rising profitability, and emerging enterprise strategy form the foundation of an attractive new investment story.

Previously we covered a bullish thesis on Upwork Inc. by Oliver | MMMT Wealth in December 2024, which highlighted strong revenue growth, expanding margins, and rising free cash flow. The company’s stock price has appreciated approximately by 17.92% since our coverage. This is because the thesis played out. The thesis still stands as Upwork continues strengthening monetization. Stefan Waldhauser shares a similar view but emphasizes the company’s turnaround and enterprise expansion.

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Disclosure: None.