Five9 Inc vs Upwork Inc — how do they compare? Five9 Inc trades at $31.2 (market cap $2.44B), while Upwork Inc trades at $8.31 (market cap $1.04B). The key difference: Five9 Inc is far larger — about 2.3× Upwork Inc's market cap, and Five9 Inc is trading nearer its 52-week high, Upwork Inc nearer its low. Which is the better fit depends on your goals.
| FIVN | UPWK | |
|---|---|---|
Market Cap | $2.44B | $1.04B |
Sector | Technology | Industrials |
52-Week High | $34.48 | $22.11 |
52-Week Low | $13.61 | $7.84 |
Enterprise Value | $2.59B | $806.15M |
Signals from Pluang's Aura AI — not financial advice
Five9 (FIVN) trades at $31.14, down 9.69% today but remains near its 52-week highs. The stock shows strong technical momentum with bullish moving averages and has consistently beaten earnings estimates in recent quarters. Revenue growth accelerated to 10% in Q2 2026, reaching $312.4 million, while the company maintains a solid gross margin of 54.91%. Recent management appointments and AI-driven subscription growth provide positive catalysts.
The outlook remains positive with 61% analyst buy ratings and a $32.67 consensus target offering 5% upside. However, elevated valuation multiples (P/E 47.99) and ongoing fiduciary investigations pose risks. The stock's trajectory depends on continued execution of AI revenue growth and margin expansion targets.
Upwork (UPWK) stock is trading at $8.385, down 14.7% on the day following Q2 2026 results. While the company beat earnings expectations with EPS of $0.41 versus $0.3424, weak forward guidance triggered the sell-off. The stock exhibits a bearish technical signal, trading near key support levels. Fundamentally, the company maintains solid profitability metrics, including a 77.21% gross margin and a P/E ratio of 10.71, but faces headwinds from declining active client counts and AI-related market shifts.
The outlook is cautious. Analyst consensus remains a 'Buy' with a $9.25 price target, suggesting potential upside from current levels. However, near-term risks are elevated due to the guidance miss, ongoing client attrition, and potential legal investigations. The stock's valuation appears reasonable, but investor confidence hinges on the company's ability to stabilize client growth and navigate the AI disruption in the freelance market.
Trailing returns across standard periods
Latest headlines on both assets
Five9 provides cloud-native contact center software that enables digital customer service, sales, and marketing engagement. The company's Virtual Contact Center platform combines core telephony functionality, omnichannel engagement capabilities, and various software modules into a unified cloud contact-center-as-a-service, or CCaaS, platform. Five9's artificial intelligence and automation portfolio supplements and enhances the firm's core CCaaS offerings, including solutions for digital self-service, agent assist technology, and workflow automation. Five9 also offers workforce optimization products that optimize call center efficiency through workforce management solutions, manage interaction quality, and track agent performance.
Read more on FIVN →Upwork Inc is a United States-based company that operates an online marketplace that enables businesses to find and work with highly-skilled independent professionals. The develops platform for hiring and freelancing purposes. Its products offering include Upwork Basic, Upwork Plus, Upwork Business, Upwork Enterprise, and Upwork Payroll. The business generates revenue from Talent and Clients across the USA, India, the Philippines and the rest of the world. Substantial income is derived from providing services to Clients.
Read more on UPWK →