Five9 Inc vs White Mountains Insurance Group Ltd. Common Stock — how do they compare? Five9 Inc trades at $33.37 (market cap $2.47B), while White Mountains Insurance Group Ltd. Common Stock trades at $2,090 (market cap $5.01B). The key difference: White Mountains Insurance Group Ltd. Common Stock is far larger — about 2× Five9 Inc's market cap, and White Mountains Insurance Group Ltd. Common Stock pays a 0.05% dividend while Five9 Inc pays none. Which is the better fit depends on your goals.
| FIVN | WTM | |
|---|---|---|
Market Cap | $2.47B | $5.01B |
Volume | 1,632,106 | 19,324 |
Sector | Technology | Financials |
52-Week High | $38.65 | $2.32K |
52-Week Low | $13.61 | $1.85K |
Typical Hold Time | 72 Days | — |
Enterprise Value | $2.62B | $5.84B |
Dividend Yield | — | 0.05% |
Signals from Pluang's Aura AI — not financial advice
Five9 (FIVN) trades at $35.41, down 0.73% on the day, with strong technical momentum showing bullish moving averages and neutral oscillators. The company demonstrates accelerating revenue growth, reaching $1.15B in 2025 with improving profitability as net income turned positive at $39.42M. Recent AI revenue surged 78% to $39M, now representing 15% of subscription revenue, driving investor optimism.
The outlook remains positive with analyst consensus at Buy (61%) and $34 price target, though current price exceeds consensus. Key risks include competitive CCaaS market pressure and insider selling activity. Revenue growth momentum and AI adoption provide upside potential, but valuation multiples remain elevated with P/E of 52 requiring sustained execution.
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
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 →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 →