BigBear.ai vs. Five9: Which AI-Driven Software Stock Is the Better Buy Now?

Artificial intelligence is transforming the software landscape, and two companies at the forefront — BigBear.ai BBAI and Five9 FIVN — are drawing investor attention. BigBear.ai specializes in AI-powered decision intelligence and predictive analytics primarily for government and defense applications. Meanwhile, Five9 operates in the cloud contact center software space, integrating generative AI into customer experience (CX) platforms for commercial enterprises.

Both companies are leveraging AI to solve complex problems across industries. Their innovations span from defense-grade analytics to enterprise-grade AI agents. With distinct end-markets and operating models, comparing BigBear.ai and Five9 offers investors a timely look at two vastly different ways AI is being commercialized. One stock is striving for profitability and execution stability, while the other is already delivering margin expansion and growth acceleration.

Let’s dive deep and closely compare the fundamentals of the two stocks to determine which one is a better investment now.

The Case for BigBear.ai Stock

BigBear.ai is attempting a strategic pivot toward sustainable growth under a new CEO, Kevin McAleenan. With deep roots in national security and border management, the company’s core strength lies in deploying AI for critical infrastructure, defense, and homeland security applications. Its platforms like Orion, ConductorOS, and Shipyard.ai are tailored to address complex challenges in mission-critical settings, giving BigBear.ai a defensible niche.

Backlog growth of 30% year over year to $385 million signals longer-term customer confidence, particularly with new contract wins like the Department of Defense’s Orion platform and partnerships with Austal USA. 

Still, the near-term financial picture is troubled. While BigBear.ai is innovating aggressively—especially through international expansion and commercial crossovers from its Pangiam security technology—the company’s lumpy revenue model, non-GAAP losses, and limited commercial diversification expose investors to significant risk.

In first-quarter 2025, BigBear.ai reported revenue of $34.8 million, missing estimates and showing only 5% year-over-year growth. Its adjusted EBITDA came in at a loss of $7 million, reflecting growing R&D spend and delayed federal funding cycles. While the company ended the quarter with a much-improved $108 million in cash, up significantly from the prior quarter and the prior-year quarter, this buffer is necessary given ongoing losses and volatility in government procurement.

The Case for Five9 Stock

Five9 presents a mature, scalable enterprise SaaS company capitalizing on the generative AI boom in customer experience. Its AI-powered “Genius” platform integrates seamlessly with enterprise systems like Salesforce and ServiceNow, and provides self-service AI agents, transcription, agent assist, and intelligent routing capabilities. These solutions are increasingly mission-critical for large brands optimizing customer service with automation.

In first-quarter 2025, Five9 reported revenues of $279.7 million, up 13.2% year over year and ahead of guidance. Subscription revenue, which is 80% of total revenue, rose 14% year over year, while enterprise AI revenue surged 32% year over year and now comprises 9% of enterprise subscription revenue. The company delivered record free cash flow of $34.9 million, adjusted EBITDA margin of 18.8% (up 360 basis points year over year), and EPS of 62 cents (up 29% from a year ago)—all pointing to disciplined execution.

Five9’s momentum is also reflected in rising demand among Fortune 500 clients, with major wins across healthcare, financial services, and mobility. It is deepening AI adoption in its install base via its AI Blueprint program, which boasts a 50% conversion rate. Moreover, strategic partnerships with Salesforce CRM, Google Cloud, IBM watsonx and ServiceNow NOW enhance Five9’s platform reach and monetization potential. The recent launch of Five9 Fusion provides native AI-powered customer experience enhancements inside Salesforce, improving sales adoption. Additionally, the ServiceNow integration enables AI-powered real-time transcription and workflow routing, while the IBM watsonx collaboration offers clients optionality in large language model selection. 

Despite macroeconomic headwinds and some sales cycle elongation, particularly in international markets, Five9 reaffirmed its $1.14 billion full-year revenue guidance and raised EPS guidance. Its operating leverage, robust AI-led growth engine, and expanding free cash flow place it on track to exceed the Rule of 40 metrics by 2027.

BBAI & FIVN Stock Performances

BigBear.ai stock is up 13% over the past three months, outperforming the Zacks Computer and Technology sector. However, BBAI stock is down 10.1% year to date.

Over the past three months, Five9 shares are down about 13% and down 34% year to date. This slump came as investors worried about tech stocks and Five9’s slowing growth rates, but the recent first-quarter beat has sparked a partial recovery.

Still, at current levels, the stock remains well below its 52-week high of $49.90. Wall Street analysts see considerable upside from here – the average price target for Five9 is about 37.6% higher than the most recent current price.

Share Price Performance

Valuation of BBAI & FIVN Stocks

At around $4.00 per share (as of Friday), BigBear.ai’s valuation isn’t cheap. The company trades at about 6.59× forward 12-month trailing sales, much higher than FIVN’s 1.71 ratio. At $26.85 per share, FIVN trades at roughly 1.71× trailing 12-month sales – a price-to-sales ratio that is quite low for a software company with double-digit growth.

BBAI & FIVN Estimate Revision Trend

Earnings estimate trend for FIVN has been trending upward, whereas the market remains skeptical about BigBear’s ability to translate its contract pipeline into sustained profitability. The loss estimate has widened over the past 60 days for BBAI stock. The estimated figure for FIVN’s 2025 EPS reflects 11.7% growth from 2024. While BBAI is expected to report a loss of 41 cents per share, narrower than the year-ago loss of $1.10 per share.

For BBAI

For FIVN

Which Stock Has More Upside Now?

Both BigBear.ai and Five9 are leveraging AI to fuel their businesses, but they occupy different ends of the risk spectrum. BigBear.ai offers exposure to a cutting-edge, government-focused AI niche and has the potential for explosive gains if it can convert its hefty backlog into profitable growth. However, with its small size, ongoing losses, and dependence on government contract timing, BigBear.ai’s stock is highly speculative and prone to big swings. The current Zacks Rank #4 (Sell) on BBAI reflects these near-term concerns.

Five9, on the other hand, presents a more established growth story in the AI software space. It is already generating over a billion dollars in revenues with improving margins, and its contact-center AI solutions address a massive market. The stock’s sharp decline earlier this year has left it trading at a reasonable valuation, and analysts see a meaningful upside if performance continues on its current track. Five9 carries a Zacks Rank #2 (Buy) presently, signaling upward earnings estimate revisions and a favorable outlook. You can see the complete list of today’s Zacks #1 Rank (Strong Buy) stocks here.

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This article originally published on Zacks Investment Research (zacks.com).

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