DoubleVerify and Five9 Offer Contrasting Paths for Mid-Cap Software Investors, Analysis Shows

An analysis of U.S. mid-cap software companies has identified DoubleVerify (DV) and Five9 (FIVN) as two distinct investment candidates, with one offering strong free cash flow and the other presenting significant growth potential through artificial intelligence, according to a report from Investing.com.

DoubleVerify: A Focus on Cash-Flow Quality

DoubleVerify stands out for its ability to convert revenue growth into cash, the analysis noted. The company's financial performance shows a clear trend of scaling profitability.

• Revenue grew from $332.74 million in 2021 to $748.29 million in 2025.
• Levered free cash flow (FCF) increased from $73.35 million to $172.65 million over the same period.

Citing a May 6, 2026, update, the report mentioned that DoubleVerify's management reaffirmed its 2026 revenue guidance of $810 million to $826 million and targeted an adjusted EBITDA margin of approximately 34%. Potential risks include the cyclical nature of digital advertising budgets and pressure on earnings from product investment.

Five9: Betting on AI-Led Growth

Five9 is highlighted for its growth trajectory and a significant inflection in cash generation, driven by opportunities in AI. The company has demonstrated a notable turnaround in its ability to produce cash.

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• Revenue climbed from $609.59 million in 2021 to $1.15 billion in 2025.
• Levered FCF improved from a negative $13.22 million to a positive $201.24 million during that time.

According to an August 6, 2026, report, Five9 raised its 2026 revenue guidance and lifted its AI revenue-growth expectations to at least 60%, targeting approximately $175 million of FCF for the year. However, the analysis also points to intense competition and notes that the stock's recent 110.74% six-month gain may already reflect high expectations.

Contrasting Investment Profiles

The two companies present different propositions for investors, according to the report's conclusion. DoubleVerify is positioned as the steadier, value-oriented candidate due to its strong and consistent free cash flow profile relative to its valuation.

In contrast, Five9 represents a higher-growth opportunity with greater potential upside, but its success is more dependent on executing its AI monetization strategy in a competitive market. The report frames it as a higher-expectation candidate where execution is critical.