Upwork Inc vs White Mountains Insurance Group Ltd. Common Stock — how do they compare? Upwork Inc trades at $8.44 (market cap $1.08B), while White Mountains Insurance Group Ltd. Common Stock trades at $2,096.01 (market cap $5.00B). The key difference: White Mountains Insurance Group Ltd. Common Stock is far larger — about 4.6× Upwork Inc's market cap, and White Mountains Insurance Group Ltd. Common Stock pays a 0.05% dividend while Upwork Inc pays none. Which is the better fit depends on your goals.
| UPWK | WTM | |
|---|---|---|
Market Cap | $1.08B | $5.00B |
Volume | 2,181,968 | 16,109 |
Sector | Industrials | Financials |
52-Week High | $22.11 | $2.32K |
52-Week Low | $7.84 | $1.85K |
Typical Hold Time | 38 Days | — |
Enterprise Value | $842.37M | $5.83B |
Dividend Yield | — | 0.05% |
Signals from Pluang's Aura AI — not financial advice
UPWK trades at $8.43, down 2.09% today, with mixed technical signals showing bullish moving averages but overbought RSI levels. The company maintains strong profitability with 77.21% gross margins and 12.93% net income margin, though recent earnings showed two misses out of three quarters. Revenue growth has slowed from 28.02% in 2024 to 14.65% in 2025, with Q3 2026 earnings pending. Institutional buying interest exists with Bank of America acquiring 704,083 shares in September 2026.
UPWK presents a compelling value case with low P/E of 11.08 and P/S of 1.49, trading below the $9.64 consensus target. However, AI disruption to freelance markets and declining active client counts pose significant risks. The stock offers 14% upside to analyst targets but faces execution challenges amid industry transformation.
White Mountains Insurance Group (WTM) trades at $2,093.13, up 0.31% with neutral technical signals. The stock shows strong fundamentals with a P/E of 4.8 and ROE of 21.9%, though recent earnings were mixed with Q2 2026 beating estimates while Q1 missed. Book value per share reached $2,258 as of June 2026, up 4% quarterly. Recent product launches and board additions signal strategic growth initiatives.
WTM presents value investment appeal with attractive valuation multiples and solid profitability, but faces execution risks from volatile quarterly earnings and negative cash flow trends. Analyst consensus remains neutral with 100% hold ratings, suggesting cautious optimism pending clearer earnings consistency and cash flow improvement.
Trailing returns across standard periods
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 →White Mountains Insurance Group Ltd. is a Bermuda-based holding company that owns and builds insurance and financial services businesses. Its operating segments include Ark, a specialty insurance and reinsurance underwriter; HG Global, which reinsures municipal bond insurer Build America Mutual; and Kudu Investment Management, which provides capital to boutique asset managers.
Read more on WTM →