Five9 (FIVN) AI Stock Analysis

• Market Cap: $1.35B
• Dividend Yield: N/A
• Average Volume (3M): 2.81M
• Price to Earnings (P/E): 39.4
• Beta (1Y): 1.76
• Revenue Growth: 12.48%
• EPS Growth: N/A
• Country: US
• Employees: 3,073
• Sector: Technology
• Sector Strength: 88
• Industry: Software - Infrastructure
• EPS (TTM): 0.80
• Shares Outstanding: 76,495,680
• 10 Day Avg. Volume: 3,628,161
• 30 Day Avg. Volume: 2,812,907
• PEG Ratio: -0.10
• Price to Book (P/B): 1.98
• Price to Sales (P/S): 1.35
• P/FCF Ratio: 7.72
• Enterprise Value/Market Cap: 1.49
• Enterprise Value/Revenue: 1.75
• Enterprise Value/Gross Profit: 3.21
• Enterprise Value/Ebitda: 12.94
• 1Y Price Target: $27.50
• Price Target Upside: 53.72% Upside
• Rating Consensus: Moderate Buy
• Number of Analyst Covering: 17
• EPS Forecast (FY): 3.19
• Revenue Forecast (FY): $1.25B

• Rating: 63 Neutral
• Price Target: $18.50 ▲(3.41% Upside)
• Action: Reiterated Date: 02/21/26
• Date: Action: Reiterated 02/21/26

The score is driven mainly by improving fundamentals and strong cash generation, reinforced by constructive 2026 guidance and continued Enterprise AI momentum. Offsetting these positives are weak technical trend signals and a demanding valuation, with leverage and retention/margin dynamics adding execution risk.

Positive Factors

Strong cash generation and free cash flow

Sustained, material free cash flow provides durable optionality: it funds product investment, AI capacity, share repurchases and debt paydown without relying on capital markets. Consistent cash conversion reduces execution risk and supports reinvestment as scale expands.

Enterprise AI momentum with attractive AI economics

AI is the fastest-growing segment and has reached meaningful scale. High-margin AI offerings expand gross-margin potential and create upsell/capacity revenue streams, strengthening long-term unit economics and differentiation as customers shift to AI-driven CX solutions.

High subscription mix and concentrated enterprise base

A recurring subscription model with a large, growing cohort of >$1M ARR enterprise customers improves revenue durability and upsell potential. High subscription mix supports predictable recurring cash flow and increases lifetime value from installed-base expansion.

Negative Factors

Relatively high leverage for a software company

A roughly 1.0x debt-to-equity position leaves less financial flexibility than typical SaaS peers. Elevated leverage increases sensitivity to margin or growth slips, limits ability to opportunistically invest or M&A, and raises refinancing and interest-rate risk over the medium term.

Gross-margin pressure from telecom usage and services mix

Lower-margin telecom usage and professional services are structurally dilutive unless offset by higher-margin AI mix. Persistent usage or services penetration could cap gross-margin expansion, making long-term margin upside dependent on successful product mix shift to AI and subscription services.

Revenue predictability exposed by consumption-based AI and guidance profile

Consumption-driven AI introduces quarter-to-quarter variability and makes backlog conversion timing less certain. Back-end loaded guidance plus a slight dollar-based retention step-down increase execution risk and reduce near-term revenue visibility for planning and investment decisions.

Five9 Business Overview & Revenue Model

Company Description

Five9, Inc., together with its subsidiaries, provides cloud software for contact centers in the United States and internationally. The company offers virtual contact center cloud platform that delivers a suite of applications, which enables the breadth of contact center-related customer service, sales, and marketing functions. Its solution enables its clients to manage these customer interactions across various channels, including voice, video, chat, email, website, social media, click-to-call, callback, and mobile channels, as well as through APIs; and provides natural language processing and automatic speech recognition solutions. The company serves customers in various industries comprising banking and financial services, business process outsourcers, consumer, healthcare, technology, and education. Five9, Inc. was incorporated in 2001 and is headquartered in San Ramon, California.

How the Company Makes Money

Five9 generates revenue primarily through a subscription-based model, where customers pay for access to its cloud contact center software and services. This includes tiered pricing based on the number of users and the level of features required. Key revenue streams include recurring software subscriptions, professional services for implementation and training, and ongoing support and maintenance. Additionally, Five9 has formed strategic partnerships with other technology providers and telecommunications companies, which enhance its service offerings and contribute to its earnings through bundled solutions and shared customer bases.

Five9 Financial Statement Overview

Summary

Strong multi-year revenue scaling and a meaningful turn to profitability in 2025 are supported by robust operating cash flow and free cash flow. The primary offset is still-elevated leverage for a software company (roughly 1.0x debt-to-equity), which reduces flexibility if growth or margins soften.

Income Statement

Revenue has scaled materially over the last several years (from $435M in 2020 to $1.15B in 2025), with gross margin holding relatively steady in the mid-50% range. Profitability has improved meaningfully, moving from sizable losses in 2021–2023 to positive net income in 2025 (about a 3.4% net margin). The key weakness is that operating profitability remains modest versus revenue scale, and the business only recently returned to consistent profitability, which increases sensitivity to any growth slowdown.

Balance Sheet

Leverage remains a notable constraint: total debt is high at ~$805M versus equity of ~$786M in 2025 (about 1.0x debt-to-equity). This is improved from 2021–2022 when debt-to-equity was much higher, indicating balance sheet strengthening over time. Still, the capital structure is relatively levered for a software company, and returns to equity holders have been pressured historically given prior losses.

Cash Flow

Cash generation is a clear strength. Operating cash flow increased to ~$226M in 2025 and free cash flow rose to ~$201M, with a strong year-over-year rebound in free cash flow. Free cash flow is substantial relative to earnings, suggesting good cash conversion and improving underlying efficiency. The main caution is that cash flow performance has been more uneven in earlier years, so durability through cycles remains something to monitor.

Breakdown	Dec 2025	Dec 2024	Dec 2023	Dec 2022	Dec 2021
Income Statement
Total Revenue	1.15B	1.04B	910.49M	778.85M	609.59M
Gross Profit	628.03M	564.40M	477.80M	411.35M	338.49M
EBITDA	163.89M	54.96M	-23.26M	-38.10M	-8.82M
Net Income	39.42M	-12.79M	-81.76M	-94.65M	-53.00M
Balance Sheet
Total Assets	1.79B	2.05B	1.49B	1.24B	1.19B
Cash, Cash Equivalents and Short-Term Investments	696.92M	1.01B	730.30M	614.26M	469.86M
Total Debt	847.21M	1.23B	793.88M	790.56M	825.51M
Total Liabilities	1.00B	1.43B	956.48M	934.52M	981.81M
Stockholders Equity	785.82M	622.19M	538.09M	309.96M	211.13M
Cash Flow
Free Cash Flow	201.24M	78.56M	97.60M	32.69M	-13.22M
Operating Cash Flow	226.21M	143.17M	128.84M	88.86M	29.00M
Investing Cash Flow	122.31M	-266.55M	-259.56M	30.96M	-150.48M
Financing Cash Flow	-478.57M	342.73M	94.58M	-30.23M	-7.50M

Five9 Technical Analysis

• Technical Analysis Sentiment: Neutral
• Last Price: 17.89
• 50DMA: Negative
• 100DMA: Negative
• 200DMA: Negative
• MACD: Negative
• RSI: Neutral
• STOCH: Neutral

Evaluating momentum and price trends is crucial in stock analysis to make informed investment decisions. For FIVN, the sentiment is Neutral. The current price of 17.89 is above the 20-day moving average (MA) of 17.35, below the 50-day MA of 18.33, and below the 200-day MA of 23.14, indicating a neutral trend. The MACD of -0.09 indicates Negative momentum. The RSI at 50.62 is Neutral, neither overbought nor oversold. The STOCH value of 28.64 is Neutral, not indicating any strong overbought or oversold conditions. Overall, these indicators collectively point to a Neutral sentiment for FIVN.

Five9 Peers Comparison

Name	Overall Rating	Market Cap	P/E Ratio	ROE	Dividend Yield	Revenue Growth	EPS Growth
CSGS	70 Outperform	$2.28B	38.01	28.84%	1.66%	3.30%	31.18%
ATEN	70 Outperform	$1.46B	30.33	19.01%	1.33%	10.27%	3.52%
EVCM	65 Neutral	$2.08B	45.30	0.04%	―	-11.61%	99.07%
FIVN	63 Neutral	$1.35B	39.43	5.60%	―	12.48%	―
Sector *	61 Neutral	$37.18B	12.37	-10.20%	1.83%	8.50%	-7.62%

Five9 Corporate Events

Five9 Amends Cooperation Agreement to Extend Board Alignment

On December 8, 2024, Five9, Inc. entered into a cooperation letter agreement with investment firm Anson and related parties, formalizing terms around board representation and governance. On February 17, 2026, the company and Anson amended this agreement to solidify their ongoing cooperation and clarify future board nomination and voting arrangements.

Under the amendment, Five9 will nominate existing director Sagar Gupta for election to its board at the 2026 Annual Meeting of Stockholders, reinforcing continuity in board composition. Anson, in turn, agreed to extend its voting and standstill obligations until a date tied to the nomination deadlines for the 2027 annual meeting, signaling continued alignment between the company and this shareholder group and helping reduce the risk of near-term governance disputes.

The most recent analyst rating on (FIVN) stock is a Buy with a $25.00 price target. To see the full list of analyst forecasts on Five9 stock, see the FIVN Stock Forecast page.

Five9 Guides 2026 Growth After Record 2025 Results

Five9 reported record 2025 revenue of $1.15 billion, up 10% from 2024, with GAAP results swinging from a $12.8 million loss to a $39.4 million profit and operating cash flow rising to $226.2 million. The company expanded GAAP and adjusted margins, lifted adjusted EBITDA to $269.7 million, and saw strong Q4 metrics, including 12% subscription revenue growth, 50% enterprise AI revenue growth, and record quarterly operating cash flow of $83.6 million, underscoring its positioning in the fast-evolving AI-driven CX market.

For 2026, Five9 guided to further top-line and earnings growth, projecting full-year revenue between $1.247 billion and $1.261 billion and higher GAAP and non-GAAP EPS, while first-quarter guidance called for revenue up to $302.5 million and continued profitability. The company also scheduled its 2026 annual shareholder meeting for May 20, 2026, to be held virtually, marking an ongoing shift toward digital shareholder engagement alongside its strategy to capitalize on AI-centric demand in contact centers.

The most recent analyst rating on (FIVN) stock is a Buy with a $20.00 price target. To see the full list of analyst forecasts on Five9 stock, see the FIVN Stock Forecast page.

Five9 Announces CEO Succession and Governance Transition Plan

On January 20, 2026, Five9’s board approved an Amended and Restated Employment Transition Agreement that formalizes the succession from current CEO Michael Burkland to incoming CEO Amit Mathradas, who is set to take over effective February 2, 2026. Under the new agreement, Burkland will remain CEO until the transition date, continue as a director and Chairman of the Board through the 2026 annual meeting of stockholders, and then serve as a paid consultant for one year, during which time his existing equity awards will keep vesting but he will receive no new equity grants and limited additional board compensation; the board also plans to reduce its size by one seat after his departure and appoint an independent chairman by the 2026 annual meeting, signaling a structured leadership handover and a shift toward strengthened governance and independent oversight for stakeholders.

The most recent analyst rating on (FIVN) stock is a Buy with a $19.50 price target. To see the full list of analyst forecasts on Five9 stock, see the FIVN Stock Forecast page.

Five9 Announces New CEO Amid Leadership Transition

Five9, Inc. announced that Amit Mathradas will assume the role of Chief Executive Officer and join its Board of Directors effective February 2, 2026, succeeding Michael Burkland, who will remain on the Board. Mathradas brings extensive experience in leadership roles within the tech industry, having served in senior positions at companies like Nintex USA, Avalara, and PayPal, which is expected to bolster Five9’s strategic initiatives and enhance its standing in the competitive cloud software market. The terms of his compensation and performance-based incentives highlight a strong, results-driven approach to aligning his leadership with shareholder value, potentially reinforcing Five9’s market position and long-term growth trajectory.

The most recent analyst rating on (FIVN) stock is a Hold with a $22.00 price target. To see the full list of analyst forecasts on Five9 stock, see the FIVN Stock Forecast page.