Five9, Inc. (NASDAQ:FIVN) Appoints New CEO While Momentum Signals Near-Term Weakness

Management transition and analyst repositioning mark a pivotal phase; balance-sheet strength supports strategic moves while price action and momentum point toward near-term downside pressure.

Recent News

Jan. 2026: Company announced appointment of Amit Mathradas as Chief Executive Officer effective February 2026. Dec. 15, 2025: Five9 earned placement on Computerworld’s 2026 Best Places to Work in IT list. Dec. 4–5, 2025: Company president reported sale of 8,212 shares in open-market transactions, per regulatory filing. Jan. 2026: several brokers published lowered price targets and adjustments to ratings amid ongoing commercial execution updates and partnership announcements, and reports noted an expanded Google Cloud collaboration.

Technical Analysis

Directional indicators show trend strength: ADX at 27.17 signals a strong underlying trend; DI+ peaked then reversed while DI- dipped then reversed, a combination that reads as a bearish directional shift and increases near-term downside risk relative to the current valuation.

MACD sits negative at -0.68 with a peak-and-reversal trend and a signal line at -0.65; that configuration denotes declining momentum and confirms bearish pressure that conflicts with any immediate upside narrative tied to valuation support.

MRO registers -32.06 and trends downward; the negative reading indicates price presently sits below the WMDST target and carries potential upside pressure toward that valuation, but the magnitude implies a meaningful gap rather than a trivial mismatch.

RSI at 41.58 with a peak-and-reversal trend shows momentum has rolled over from higher levels and now sits below neutral, reinforcing the near-term bearish bias while leaving room for mean-reversion if buying interest reappears.

Price sits below short-, medium- and long-term averages: close $16.33 beneath the 50-day average $19.06 and the 200-day average $23.61; 12-day EMA and 26-day EMA both declining. Price near the lower Bollinger band ($16.36 at 1× std dev) suggests compression close to the recent lower bound, increasing the likelihood of volatile tradable swings against the wider bearish backdrop.

Volatility and volume context amplify the message: 42-day beta 1.69 and 52-week beta 1.84 indicate above-market sensitivity, while 10- and 50-day average volumes exceed the most recent session, implying episodic liquidity that can accelerate directional moves away from the valuation anchor.

 


Fundamental Analysis

Profitability: EBIT $21,703,000 yields an EBIT margin of 7.59%, well below the industry peer mean 36.20% and industry peer median 45.06%, and positioned inside the peer range toward the lower bound. Operating margin registers 5.61% and mirrors that relative weakness versus peer benchmarks.

Growth: reported total revenue $285,832,000. QoQ revenue change shows -28.96% and year-over-year revenue change shows -81.14% as provided; sequential and annual growth figures indicate material variability that reduces clarity around near-term top-line momentum despite product-level AI traction reported elsewhere.

Cash flow and liquidity: operating cash flow $59,196,000 and free cash flow $38,301,000 produce a free cash flow yield of 2.03%. Cash and short-term investments total $676,156,000 and current ratio stands at 4.61 with a cash ratio of 3.29, giving material near-term liquidity to fund buybacks, investments, or balance-sheet flexibility tied to strategic execution.

Leverage and coverage: total debt $798,006,000 produces debt-to-equity 102.93% and debt-to-EBITDA ~18.75; interest coverage about 7.03x. The capital structure shows meaningful leverage relative to operating earnings but adequate interest coverage at current earnings levels.

Earnings and valuation signals: EPS actual $0.78 versus estimate $0.73, an EPS surprise ratio of 6.85%. Trailing P/E stands at 116.22 while forward P/E sits near 41.48; price-to-book 2.43 and enterprise multiple 47.16. Those multiples reflect market pricing for recovery and margin expansion rather than the present reported margins.

WMDST valuation view: WMDST values the stock as under-valued, reflecting the firm’s assessment of long-term cash generation potential relative to current market price and available liquidity, though execution and momentum metrics create a near-term performance headwind.

MOST-RECENT QUARTERLY REPORT
REPORT PERIOD ENDING: 2025-09-30
REPORT DATE: 2025-11-06
NEXT REPORT DATE: 2026-02-05
CASH FLOW  Begin Period Cash Flow 207.6 M
 Operating Cash Flow 59.2 M
 Capital Expenditures -20.89 M
 Change In Working Capital -36.00 M
 Dividends Paid
 Cash Flow Delta -12.14 M
 End Period Cash Flow 195.4 M
 
INCOME STATEMENT REVENUE
 Total Revenue 285.8 M
 Forward Revenue 247.1 M
COSTS
 Cost Of Revenue 128.6 M
 Depreciation 20.9 M
 Depreciation and Amortization 20.9 M
 Research and Development 35.2 M
 Total Operating Expenses 269.8 M
PROFITABILITY
 Gross Profit 157.3 M
 EBITDA 42.6 M
 EBIT 21.7 M
 Operating Income 16.0 M
 Interest Income 5.7 M
 Interest Expense 3.1 M
 Net Interest Income 2.6 M
 Income Before Tax 18.6 M
 Tax Provision 643.0 K
 Tax Rate 3.454 %
 Net Income 18.0 M
 Net Income From Continuing Operations 18.0 M
EARNINGS
 EPS Estimate 0.73
 EPS Actual 0.78
 EPS Difference 0.05
 EPS Surprise 6.849 %
 Forward EPS 0.79
 
BALANCE SHEET ASSETS
 Total Assets 1.8 B
 Intangible Assets 420.9 M
 Net Tangible Assets 354.4 M
 Total Current Assets 949.4 M
 Cash and Short-Term Investments 676.2 M
 Cash 193.4 M
 Net Receivables 117.1 M
 Inventory
 Long-Term Investments 8.0 M
LIABILITIES
 Accounts Payable 30.4 M
 Short-Term Debt
 Total Current Liabilities 205.7 M
 Net Debt 541.1 M
 Total Debt 798.0 M
 Total Liabilities 993.1 M
EQUITY
 Total Equity 775.3 M
 Retained Earnings -397.94 M
VALUATION & PER-SHARE METRICS EQUITY & PER-SHARE METRICS
 Book Value Per-Share 10.03
 Shares Outstanding 78.214 M
 Revenue Per-Share 3.70
VALUATION
 Market Capitalization 1.9 B
 Enterprise Value 2.0 B
 Enterprise Multiple 47.159
Enterprise Multiple QoQ -46.256 %
Enterprise Multiple YoY -66.94 %
Enterprise Multiple IPRWA high: 725.943
mean: 90.514
median: 78.121
FIVN: 47.159
low: -500.562
 EV/R 7.023
CAPITAL STRUCTURE
 Asset To Equity 2.281
 Asset To Liability 1.781
 Debt To Capital 0.507
 Debt To Assets 0.451
Debt To Assets QoQ -3.774 %
Debt To Assets YoY 109.295 %
Debt To Assets IPRWA high: 1.164
FIVN: 0.451
mean: 0.171
median: 0.095
low: 0.001
 Debt To Equity 1.029
Debt To Equity QoQ -7.642 %
Debt To Equity YoY 34.471 %
Debt To Equity IPRWA high: 2.803
FIVN: 1.029
mean: 0.29
median: 0.167
low: -1.761
PRICE-BASED VALUATION
 Price To Book (P/B) 2.432
Price To Book QoQ -17.616 %
Price To Book YoY -43.024 %
Price To Book IPRWA high: 32.156
mean: 12.36
median: 10.455
FIVN: 2.432
low: -17.466
 Price To Earnings (P/E) 116.218
Price To Earnings QoQ 218.088 %
Price To Earnings YoY 142.554 %
Price To Earnings IPRWA high: 535.496
mean: 145.658
median: 137.28
FIVN: 116.218
low: -396.374
 PE/G Ratio -1.606
 Price To Sales (P/S) 6.597
Price To Sales QoQ -11.764 %
Price To Sales YoY -27.815 %
Price To Sales IPRWA high: 95.267
median: 48.871
mean: 45.874
FIVN: 6.597
low: 1.307
FORWARD MULTIPLES
Forward P/E 41.479
Forward PE/G -0.573
Forward P/S 9.629
EFFICIENCY OPERATIONAL
 Operating Leverage 266.864
ASSET & SALES
 Asset Turnover Ratio 0.165
Asset Turnover Ratio QoQ 10.249 %
Asset Turnover Ratio YoY 22.054 %
Asset Turnover Ratio IPRWA high: 0.414
FIVN: 0.165
mean: 0.127
median: 0.124
low: -0.008
 Receivables Turnover 2.511
Receivables Turnover Ratio QoQ -5.809 %
Receivables Turnover Ratio YoY -5.203 %
Receivables Turnover Ratio IPRWA high: 6.055
FIVN: 2.511
mean: 1.478
median: 1.265
low: -0.167
 Inventory Turnover
Inventory Turnover Ratio QoQ
Inventory Turnover Ratio YoY
Inventory Turnover Ratio IPRWA
 Days Sales Outstanding (DSO) 36.344
CASH CYCLE
 Cash Conversion Cycle Days (CCC) 14.402
Cash Conversion Cycle Days QoQ
Cash Conversion Cycle Days YoY -88.085 %
Cash Conversion Cycle Days IPRWA high: 226.004
FIVN: 14.402
mean: -22.591
median: -38.513
low: -211.399
CAPITAL DEPLOYMENT
 Cash Conversion Ratio 0.384
 CapEx To Revenue -0.073
 CapEx To Depreciation -1.001
 
CAPITAL, LIQUIDITY & COVERAGE CAPITAL STRUCTURE
 Total Capital 1.5 B
 Net Invested Capital 1.5 B
 Invested Capital 1.5 B
 Net Tangible Assets 354.4 M
 Net Working Capital 743.7 M
LIQUIDITY
 Cash Ratio 3.286
 Current Ratio 4.614
Current Ratio QoQ 4.029 %
Current Ratio YoY 149.156 %
Current Ratio IPRWA high: 8.127
FIVN: 4.614
mean: 1.703
median: 1.401
low: 0.159
 Quick Ratio
Quick Ratio QoQ
Quick Ratio YoY
Quick Ratio IPRWA
COVERAGE & LEVERAGE
 Debt To EBITDA 18.746
 Cost Of Debt 0.373 %
 Interest Coverage Ratio 7.03
Interest Coverage Ratio QoQ 322.536 %
Interest Coverage Ratio YoY -768.376 %
Interest Coverage Ratio IPRWA high: 225.0
median: 50.142
mean: 37.759
FIVN: 7.03
low: -266.667
 Operating Cash Flow Ratio 0.154
TIMING / LIQUIDITY
 Days Payables Outstanding (DPO) 21.942
DIVIDENDS
 Dividend Coverage Ratio
 Dividend Payout Ratio
 Dividend Rate
 Dividend Yield
PERFORMANCE GROWTH
 Asset Growth Rate 3.727 %
 Revenue Growth 0.905 %
Revenue Growth QoQ -28.964 %
Revenue Growth YoY -81.138 %
Revenue Growth IPRWA high: 28.215 %
mean: 3.108 %
median: 1.612 %
FIVN: 0.905 %
low: -13.442 %
 Earnings Growth -72.368 %
Earnings Growth QoQ -420.482 %
Earnings Growth YoY -350.877 %
Earnings Growth IPRWA high: 200.0 %
mean: 5.044 %
median: 1.918 %
FIVN: -72.368 %
low: -181.25 %
MARGINS
 Gross Margin 55.025 %
Gross Margin QoQ 0.299 %
Gross Margin YoY 2.191 %
Gross Margin IPRWA high: 90.981 %
mean: 72.527 %
median: 69.046 %
FIVN: 55.025 %
low: 26.432 %
 EBIT Margin 7.593 %
EBIT Margin QoQ 238.369 %
EBIT Margin YoY -568.704 %
EBIT Margin IPRWA high: 76.323 %
median: 45.059 %
mean: 36.204 %
FIVN: 7.593 %
low: -105.646 %
 Return On Sales (ROS) 5.613 %
Return On Sales QoQ -1118.693 %
Return On Sales YoY -446.481 %
Return On Sales IPRWA high: 76.795 %
median: 48.873 %
mean: 37.539 %
FIVN: 5.613 %
low: -133.444 %
CASH FLOW
 Free Cash Flow (FCF) 38.3 M
 Free Cash Flow Yield 2.031 %
Free Cash Flow Yield QoQ 99.509 %
Free Cash Flow Yield YoY 135.889 %
Free Cash Flow Yield IPRWA high: 10.114 %
FIVN: 2.031 %
median: 0.676 %
mean: 0.478 %
low: -10.76 %
 Free Cash Growth 77.574 %
Free Cash Growth QoQ -302.824 %
Free Cash Growth YoY -50.618 %
Free Cash Growth IPRWA high: 368.524 %
FIVN: 77.574 %
median: 0.372 %
mean: -7.421 %
low: -324.945 %
 Free Cash To Net Income 2.131
 Cash Flow Margin 11.113 %
 Cash Flow To Earnings 1.767
VALUE & RETURNS
 Economic Value Added 0.03
 Return On Assets (ROA) 1.035 %
Return On Assets QoQ 1596.721 %
Return On Assets YoY -551.965 %
Return On Assets IPRWA high: 13.583 %
median: 4.421 %
mean: 3.724 %
FIVN: 1.035 %
low: -19.283 %
 Return On Capital Employed (ROCE) 1.389 %
 Return On Equity (ROE) 0.023
Return On Equity QoQ 1339.752 %
Return On Equity YoY -392.677 %
Return On Equity IPRWA high: 0.151
median: 0.076
mean: 0.065
FIVN: 0.023
low: -0.395
 DuPont ROE 2.408 %
 Return On Invested Capital (ROIC) 1.388 %
Return On Invested Capital QoQ 301.156 %
Return On Invested Capital YoY 119.273 %
Return On Invested Capital IPRWA high: 14.226 %
median: 6.978 %
mean: 5.469 %
FIVN: 1.388 %
low: -12.344 %

Six-Week Outlook

Momentum and trend indicators favor continued near-term softness: expect price action to remain under pressure while MACD and directional indicators hold their bearish configurations. Negative MRO and proximity to the lower Bollinger band create a countervailing mean-reversion force tied to the WMDST valuation, increasing the chance of sharp, short-lived rebounds inside a broader downtrend.

Given elevated betas and above-average volume on recent moves, anticipate heightened intrarange volatility rather than steady directional drift; watch for stabilization signals when MACD momentum stops declining and RSI moves back above neutral, which would materially change the near-term technical panorama without altering the longer-term fundamental valuation anchored by WMDST.

About Five9, Inc.

Five9, Inc. (NASDAQ:FIVN) develops cloud-based contact center solutions that enhance customer interactions for businesses worldwide. Headquartered in San Ramon, California, Five9 provides a virtual contact center platform that integrates multiple communication channels, including voice, chat, email, web, social media, and mobile. This integration ensures a seamless and cohesive customer experience. The company offers a range of innovative tools such as virtual agents, agent assistance, workflow automation, and workforce engagement management, all powered by AI-driven insights. These solutions help businesses streamline customer service operations while also improving sales and marketing efforts, allowing them to quickly adapt to changing customer demands. Five9’s platform connects with enterprise applications like CRM systems, delivering real-time customer data to agents for optimized interactions and increased productivity. Serving industries such as banking, retail, healthcare, and technology, Five9 has been a reliable partner since 2001. The company’s dedication to providing customer-centric solutions continues to shape the future of contact center operations across the globe.



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