Five9, Inc. (FIVN)

Price$33.51Cached quoteAs of 2026-09-04 16:23 UTC

AI: Fair-priced

Price checkThe shares are reasonably valued overall: adjusted earnings are cheap, but ordinary profits and debt reduce safety.

Using the observed quote, the equity value is about $2.3 billion, or roughly 9.6 times management’s midpoint 2026 adjusted earnings per share. Enterprise value—a measure combining equity value and net debt—is about $2.5 billion, around 2.0 times midpoint 2026 revenue guidance. That is a supportive price signal for a growing software company. However, midpoint earnings under standard accounting rules imply roughly 41 times earnings because stock compensation and other exclusions are large. The valuation is balanced: attractive on adjusted figures, but not clearly cheap after dilution and debt.

Big pictureRevenue has expanded strongly, but growth has cooled and cash conversion relies heavily on stock-based pay.

Revenue rose from $435 million in 2020 to $1.15 billion in 2025, a strong long-term expansion, and 2026 guidance implies about 10% growth, down from 15.8% in 2023 and 12.9% in 2024, showing sensitivity to enterprise buying cycles. Operating income moved from a $98.6 million loss in 2023 to a $28.9 million profit in 2025. Operating cash flow reached $226.2 million in 2025, but $148.1 million was stock compensation. Free cash flow—cash left after operations and capital spending—was about $201 million, so durability is improving but not yet clean.

Business strengthRecurring customers and fast-growing artificial-intelligence sales support the business, though gross margins slipped.

Five9 serves more than 3,000 customers, and its last-twelve-month subscription dollar retention was 107% in Q2; above 100% means existing customers spent more overall. Q2 revenue grew 10% year over year, subscription revenue 14%, and reported artificial-intelligence revenue grew 78% to about $39 million, roughly 15% of subscription revenue. The bull case is that AI agents lift growth and margins. The caution is that Q2 adjusted gross margin fell to 61.4% from 63.0%, while core contact-center revenue grew only 7%.

What could change the storyCash and investments provide liquidity, but convertible debt and dilution leave limited downside protection.

At June 30, debt was about $805 million against $654 million of cash and marketable investments, leaving roughly $151 million of net debt; $747.5 million of convertible notes mature in 2029. First-half buybacks totaled about $101 million, and a further $200 million remained authorized. Stock compensation was $65.6 million and 8.9 million restricted units were outstanding, while reported shares fell from 77.2 million at year-end 2025 to 74.7 million at June 30. The investment case needs artificial-intelligence growth, margins, and cash generation to outpace dilution and debt obligations.

AI: News

Second-quarter resultsStrong quarterly growth and a large customer win lifted expectations, while lower margins and thin standard profits limited quality.

On August 6, Five9 reported Q2 revenue of $312.4 million, up 10% year over year, and subscription revenue up 14%. Adjusted earnings per share were $0.70 versus analysts’ $0.68 consensus, while revenue exceeded $306.6 million consensus, according to MarketBeat. Management also disclosed an approximately $100 million total-contract-value win and set full-year revenue guidance at $1.260–$1.272 billion. An independent market report said shares closed 19.8% higher the next day; timing alone does not prove the results caused all of that move.

Voice AI launchThe new voice-agent product strengthens Five9’s artificial-intelligence offer, but adoption and revenue conversion remain unproven.

On June 23, Five9 launched Voice AI Agents with human-like conversations, real-time responses, governance controls, and handoffs between artificial intelligence and human workers. The opportunity is meaningful because management said Q2 AI revenue grew 78% year over year to about $39 million, roughly 15% of subscription revenue. However, the earnings call said some customer deployments accelerated from the backlog rather than expanded deal scope, so the growth rate may be lumpy. Investors need sustained AI bookings, broader adoption, and stable margins before treating this as a permanent growth reset.

Share repurchase programFive9 committed more cash to buybacks, supporting per-share value but competing with debt reduction and product investment.

On April 30, Five9 announced a $90 million accelerated share repurchase to finish its earlier $150 million authorization and approved another $200 million program with no expiration. The first-half 2026 cash-flow data shows about $101 million of buybacks, while shares outstanding fell from 77.2 million at year-end 2025 to 74.7 million at June 30. This can lift each remaining share’s claim on earnings, but the benefit is less compelling while stock compensation remains $65.6 million in the first half and convertible debt remains substantial.

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Financial statements

	2025	2024	2023	2022	2021	2020	2019	2018	2017	2016	2015	2014	2013	2012
Revenue	$1.15B	$1.04B	$910.5M	$778.8M	$609.6M	$434.9M	$328.0M	$257.7M	$200.2M	$162.1M	$128.9M	$103.1M	$84.1M	$63.8M
Gross profit	$632.9M	$564.4M	$477.8M	$411.3M	$338.5M	$254.6M	$193.5M	$153.6M	$117.1M	$95.2M	$69.4M	$48.4M	$35.3M	$24.5M
Gross margin	55.07%	54.17%	52.48%	52.81%	55.53%	58.55%	58.99%	59.62%	58.49%	58.71%	53.83%	46.98%	41.99%	38.41%
Research & development	$152.3M	$166.2M	$156.6M	$141.8M	$106.9M	$68.7M	$45.2M	$34.2M	$27.1M	$23.9M	$22.7M	$22.1M	$17.5M	$13.2M
Operating expenses	$604.0M	$615.7M	$576.4M	$498.9M	$394.7M	$266.9M	$190.2M	$146.6M	$122.8M	$101.7M	$90.5M	$84.0M	$63.6M	$41.6M
Operating income	$28.9M	−$51.3M	−$98.6M	−$87.6M	−$56.3M	−$12.3M	$3.3M	$7.0M	−$5.7M	−$6.5M	−$21.1M	−$35.5M	−$28.3M	−$17.1M
Operating margin	2.51%	−4.92%	−10.83%	−11.25%	−9.23%	−2.83%	1.00%	2.72%	−2.86%	−4.04%	−16.41%	−34.46%	−33.66%	−26.72%
EBITDA	$90.6M	$1.6M	−$50.1M	−$42.9M	−$17.5M	$12.8M	$17.6M	$17.3M	$2.6M	$1.8M	−$13.8M	−$29.1M	−$23.9M	−$14.4M
EBITDA margin	7.89%	0.15%	−5.50%	−5.51%	−2.87%	2.94%	5.38%	6.71%	1.30%	1.14%	−10.68%	−28.19%	−28.42%	−22.61%
Net income	$39.4M	−$12.8M	−$81.8M	−$94.7M	−$53.0M	−$42.1M	−$4.6M	−$221,000	−$9.0M	−$11.9M	−$25.8M	−$37.8M	−$31.3M	−$19.3M
Net profit margin	3.43%	−1.23%	−8.98%	−12.15%	−8.69%	−9.69%	−1.39%	−0.09%	−4.48%	−7.32%	−20.05%	−36.65%	−37.22%	−30.29%
Basic EPSper basic share	$0.51	-$0.17	-$1.13	-$1.35	-$0.79	-$0.66	-$0.08	$0.00	-$0.16	-$0.23	-$0.52	-$1.00	-$7.82	-$5.82
Diluted EPSper diluted share	$0.45	-$0.17	-$1.13	-$1.35	-$0.79	-$0.66	-$0.08	$0.00	-$0.16	-$0.23	-$0.52	-$1.00	-$7.82	-$5.82

Review official source filings ↗

Owners

Reported shareholders

Reference date Jun 30, 2026

9.48%of listed shares

VANGUARD PORTFOLIO MANAGEMENT LLC7.08M shares · Jun 30, 2026

View holders

Top 20 reported holders of FIVN
Holder	% owned
VANGUARD PORTFOLIO MANAGEMENT LLC	9.48%7.08M shares
BlackRock, Inc.	9.47%7.07M shares
Voss Capital, LP	6.51%4.87M shares
AMERIPRISE FINANCIAL INC	5.54%4.14M shares
VANGUARD CAPITAL MANAGEMENT LLC	4.43%3.31M shares
Van Berkom & Associates Inc.	4.16%3.11M shares
Anson Funds Management LP	3.34%2.5M shares
Driehaus Capital Management LLC	3.03%2.27M shares
DIMENSIONAL FUND ADVISORS LP	2.97%2.22M shares
GEODE CAPITAL MANAGEMENT, LLC	2.90%2.16M shares
STATE STREET CORP	2.77%2.07M shares
FIRST TRUST ADVISORS LP	2.50%1.87M shares
ARMISTICE CAPITAL, LLC	2.06%1.54M shares
BANK OF AMERICA CORP /DE/	1.84%1.38M shares
AQR CAPITAL MANAGEMENT LLC	1.64%1.23M shares
SUSQUEHANNA INTERNATIONAL GROUP, LLP	1.54%1.15M shares
Point72 Asset Management, L.P.	1.49%1.11M shares
MORGAN STANLEY	1.46%1.09M shares
GOLDMAN SACHS GROUP INC	1.37%1.02M shares
Invenomic Capital Management LP	1.19%892.66K shares

Percentages use 74.72M shares of this listed class outstanding on Jun 30, 2026.

Gray completes the 100% scale. Reported positions may overlap; holders have different reporting dates.

Source: SEC Form 13F ↗Updated Sep 29, 2026 · Quarterly data

Insider buys & sells

Jul 1, 2024–Jun 30, 2026

Buys2$26.1K disclosed value

Sells (SEC code S)98$10.34M disclosed value

Transaction	Insider	Type	Shares	Price	Value	Owned after
Jun 5, 2026Form 4 · 10b5-1	Lee Bryan MChief Financial Officer	SellCommon Stock	1.5K	$24.25	$36.6K	310.0K
Jun 5, 2026Form 4 · 10b5-1	Dignan AndyPresident	SellCommon Stock	3.1K	$24.25	$74.5K	275.7K
Jun 4, 2026Form 4	Tuckness Matthew E.Chief Revenue Officer	SellCommon Stock	8.6K	$24.81	$214.5K	281.5K
Jun 4, 2026Form 4 · 10b5-1	Lee Bryan MChief Financial Officer	SellCommon Stock	4.3K	$24.81	$107.0K	311.5K
Jun 4, 2026Form 4 · 10b5-1	Lee Bryan MChief Financial Officer	SellCommon Stock	1.4K	$25.69	$36.1K	315.8K

Review ownership filings at SEC.gov ↗

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Five9, Inc. (FIVN)

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