LIVE
FIVN
Five9, Inc. · Technology
$19.40
-13.88% this month
VERSUS
⟷
COMPARE
TWLO
Twilio Inc. · Technology
$186.17
-4.99% this month
Scoreboard verdict
Across AI score, momentum, valuation, upside, operating margin
FIVN
2
TWLO
2
Comparison scoreboard
MIXED SETUPAI Score
FIVN 33.5
TWLO ✓47.6
1Y Return
FIVN -29.11%
TWLO ✓+59.56%
Fwd P/E
FIVN ✓5.14
TWLO 28.08
Target Up.
FIVN ✓+43.38%
TWLO +6.09%
Op. Margin
FIVN N/A
TWLO N/A
Metrics last refreshed: 6/20/2026
Quick take
FIVN vs TWLO Stock Comparison: AI Score, Valuation, Performance and Upside
Five9 and Twilio both address customer engagement and contact center use cases but from opposite ends: Five9 is a turnkey enterprise CCaaS solution sold to CX leaders and IT executives, while Twilio provides programmable APIs that developers use to build custom engagement and contact center experiences. They target different buyers (enterprise CX teams vs. developers) and compete differently in the market.
FIVN vs TWLO is a turnkey enterprise contact center platform (Five9) versus a programmable communications API infrastructure provider (Twilio) — Five9 wins enterprise CCaaS transformation deals as a complete solution, while Twilio's developer-first model allows custom communications experiences that no turnkey solution can match.
Live analysis · updated 6/20/2026
FIVN and TWLO are closely matched — they split the tracked metrics evenly. TWLO has delivered stronger 1-year price return (+59.56% vs -29.11%), though FIVN trades at the lower forward P/E (5.14x vs 28.08x). Analyst consensus implies meaningfully more upside for FIVN (+43.38%) than for TWLO (+6.09%).
Normalized 1Y performance
FIVN
TWLO
Recent returns
FIVN
TWLO
Analyst price targets & sentiment
FIVN · 21 analysts
STRONG BUYHOLDSTRONG SELL
Buy (1.8/5.0)
Price target range
analyst low$20.00
analyst high$47.00
analyst mean$27.81
current price$19.40
+43.4% upside to analyst mean
TWLO · 29 analysts
STRONG BUYHOLDSTRONG SELL
Buy (1.7/5.0)
Price target range
analyst low$120.00
analyst high$255.00
analyst mean$197.50
current price$186.17
+6.1% upside to analyst mean
Who should consider this stock?
FIVN may suit investors who:
- →prefer a purpose-built enterprise CCaaS platform with AI-powered IVA and agent assist replacing on-premises contact center infrastructure
- →value Five9's enterprise partnerships with Salesforce and ServiceNow driving large contact center transformation deal flow
- →want pure-play cloud contact center exposure in a market still largely running on legacy on-premises call center systems
- →are comfortable with long enterprise sales cycles and competition from Amazon Connect and Microsoft Teams Phone bundling
TWLO may suit investors who:
- →prefer the dominant programmable communications API platform with developer-led adoption across consumer-facing applications
- →value Segment CDP as a customer data management expansion beyond messaging infrastructure
- →want exposure to AI-powered communications automation as Twilio embeds LLM capabilities into messaging and contact center APIs
- →are comfortable with lower margins and profitability achieved through headcount reduction rather than organic operating leverage
Performance & AI score
| Metric | FIVN | TWLO |
|---|---|---|
| AI score | 33.5 | 47.6 |
| AI rank | #1902 | #603 |
| Latest close | $19.40 | $186.17 |
| 1M return | -13.88% | -4.99% |
| 6M return | -8.12% | +33.72% |
| 1Y return | -29.11% | +59.56% |
$10,000 invested — hypothetical growth (dividends reinvested)
How much would $10,000 be worth today if invested at the start of each period, with all dividends reinvested?
| Period | FIVN | TWLO |
|---|---|---|
| 1Y ago | $7.09K (-29.1%) started 2025-06-18 | $15.96K (+59.6%) started 2025-06-18 |
| 5Y ago | $1.06K (-89.4%) started 2021-06-18 | $5.06K (-49.4%) started 2021-06-18 |
| 10Y ago | $16.79K (+67.9%) started 2016-06-20 | $64.66K (+546.6%) started 2016-06-23 |
Hypothetical — past performance does not guarantee future results.
Valuation & upside potential
| Metric | FIVN | TWLO |
|---|---|---|
| Market cap | $1.48B | $28.26B |
| Trailing P/E | 29.84 | 282.08 |
| Forward P/E | 5.14 | 28.08 |
| Price/Sales | 1.26 | 5.33 |
| EV/Revenue | 1.41 | 5.28 |
| Analyst target | $27.81 | $197.50 |
| Target upside | +43.38% | +6.09% |
Growth, profitability & risk
| Metric | FIVN | TWLO |
|---|---|---|
| Revenue growth | 9.20% | 20.00% |
| Earnings growth | 2669.00% | 375.00% |
| EPS growth | +2669.00% | +375.00% |
| FCF margin | +23.15% | +16.60% |
| Operating margin | N/A | N/A |
| Profit margin | 4.87% | 1.96% |
| ROIC proxy | 7.66% | 1.32% |
| Return on equity | 7.66% | 1.32% |
| Dividend yield | 0.00% | 0.00% |
| Beta | 1.45 | 1.38 |
| Debt/equity | 96.47 | 13.72 |
| Current ratio | 4.51 | 4.66 |
| Quick ratio | 3.89 | 4.13 |
Drawdown & downside risk
Lower drawdown and smaller single-period drops generally indicate a smoother ride, though they do not guarantee lower future risk.
1Y risk snapshot
FIVN max drawdown53.33%
TWLO max drawdown30.34%
FIVN max wkly drop18.29%
TWLO max wkly drop26.24%
5Y risk snapshot
FIVN max drawdown93.51%
TWLO max drawdown89.57%
FIVN max wkly drop32.01%
TWLO max wkly drop43.47%
10Y risk snapshot
FIVN max drawdown93.51%
TWLO max drawdown90.36%
FIVN max wkly drop32.01%
TWLO max wkly drop43.47%
Performance metrics by period
| Period | Metric | FIVN | TWLO |
|---|---|---|---|
| 1Y | Growth | -29.11% | +59.56% |
| CAGR | -29.13% | +59.61% | |
| Sharpe ratio | -0.35 | 1.00 | |
| Max drawdown | 53.33% | 30.34% | |
| Max daily drop | 9.73% | 19.38% | |
| Max wkly drop | 18.29% | 26.24% | |
| 5Y | Growth | -89.42% | -49.36% |
| CAGR | -36.19% | -12.72% | |
| Sharpe ratio | -0.61 | -0.01 | |
| Max drawdown | 93.51% | 89.57% | |
| Max daily drop | 26.49% | 34.61% | |
| Max wkly drop | 32.01% | 43.47% | |
| 10Y | Growth | +67.92% | +546.65% |
| CAGR | +5.32% | +20.56% | |
| Sharpe ratio | 0.27 | 0.54 | |
| Max drawdown | 93.51% | 90.36% | |
| Max daily drop | 26.49% | 34.61% | |
| Max wkly drop | 32.01% | 43.47% |
Business comparison
| Category | FIVN | TWLO |
|---|---|---|
| Company | Five9, Inc. | Twilio Inc. |
| Sector | Technology | Technology |
| Industry | N/A | N/A |
| Core business | Five9 provides cloud contact center software (CCaaS) — intelligent virtual agents (IVA), omnichannel routing (voice, chat, email, social), workforce optimization, and AI-powered agent assistance for enterprise customer service operations. Its platform competes with Genesys, NICE inContact, and Amazon Connect for contact center transformation deals where enterprises replace on-premises call center infrastructure with cloud-native platforms. AI Genius and AI-powered agent assist features are embedded throughout the routing and agent desktop experience. | Twilio provides programmable communications APIs — voice, SMS, WhatsApp, video — for developers building customer engagement features into applications. Its contact center solution (Flex) is a programmable CCaaS platform that allows developers to build custom contact center experiences. While Five9 sells a turnkey CCaaS solution to enterprise buyers, Twilio Flex requires significant developer customization. Twilio Segment CDP provides the customer data layer that powers personalized engagement. |
| Investor focus | Investors track ARR growth, enterprise customer count (large accounts drive significant revenue), AI-powered IVA adoption, and the path to consistent profitability as the company scales past $1B in ARR. | Investors track messaging revenue growth, Segment CDP ARR, active customer count, and the path to profitability through cost reduction programs. |
FIVN strengths
- →Purpose-built enterprise CCaaS with deep workforce optimization, quality management, and analytics built natively into the platform
- →AI-powered intelligent virtual agents and agent assist differentiate Five9 from legacy on-premises contact center vendors in transformation deals
- →Strong partnerships with Salesforce, ServiceNow, and Microsoft allow Five9 to integrate deeply into existing enterprise CRM workflows
TWLO strengths
- →Dominant programmable communications APIs — default choice for developers building messaging, voice, and authentication into applications
- →Flex programmable CCaaS allows fully custom contact center experiences that turnkey solutions cannot provide for unique workflows
- →Segment CDP creates a unified customer data layer that powers personalized engagement across all Twilio communications channels
Risks to watch — FIVN
- →Amazon Connect and Microsoft Teams Phone compete in contact center at significant cloud bundling advantages
- →Revenue growth has moderated as the enterprise CCaaS market matures and competition from larger platforms intensifies
- →Large contact center transformation deals have long sales cycles that create revenue recognition lumps and forecasting challenges
Risks to watch — TWLO
- →SMS messaging pricing compression from alternative channels (WhatsApp, push notifications) reduces Twilio's per-transaction revenue
- →Twilio Flex requires significant developer investment that makes it unsuitable for most enterprise CCaaS evaluations looking for turnkey solutions
- →Revenue growth deceleration from 2020–2021 pandemic peaks has been severe, and profitability required significant headcount reductions
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