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Side-by-side financial comparison of Bowhead Specialty Holdings Inc. (BOW) and Five9, Inc. (FIVN). Click either name above to swap in a different company.

Five9, Inc. is the larger business by last-quarter revenue ($300.3M vs $155.7M, roughly 1.9× Bowhead Specialty Holdings Inc.). On growth, Bowhead Specialty Holdings Inc. posted the faster year-over-year revenue change (26.9% vs 7.8%).

Bowhead Specialty Holdings Inc. is a specialty insurance holding company that offers a diversified portfolio of property and casualty insurance products, focusing on underserved niche market segments primarily across North America. It provides tailored risk management solutions and specialized coverage options for both commercial and individual clients.

Five9, Inc. is a leading global provider of cloud-native contact center software and solutions. It serves enterprises of all sizes across retail, healthcare, financial services, and technology sectors, offering omnichannel customer engagement tools, AI-powered automation, workforce management, and analytics to boost customer experience and operational efficiency.

BOW vs FIVN — Head-to-Head

Bigger by revenue
FIVN
FIVN
1.9× larger
FIVN
$300.3M
$155.7M
BOW
Growing faster (revenue YoY)
BOW
BOW
+19.1% gap
BOW
26.9%
7.8%
FIVN

Income Statement — Q1 FY2026 vs Q4 FY2025

Metric
BOW
BOW
FIVN
FIVN
Revenue
$155.7M
$300.3M
Net Profit
$16.0M
Gross Margin
55.4%
Operating Margin
6.6%
Net Margin
10.3%
Revenue YoY
26.9%
7.8%
Net Profit YoY
EPS (diluted)
$0.48
$0.22

Green = leading value per metric. Periods may differ when fiscal calendars don't align.

8-Quarter Revenue & Profit Trend

Side-by-side quarterly history. Quarters aligned by calendar period so offset fiscal years line up.

Revenue
BOW
BOW
FIVN
FIVN
Q1 26
$155.7M
Q4 25
$151.7M
$300.3M
Q3 25
$143.9M
$285.8M
Q2 25
$133.3M
$283.3M
Q1 25
$122.7M
$279.7M
Q4 24
$278.7M
Q3 24
$116.8M
$264.2M
Q2 24
$98.9M
$252.1M
Net Profit
BOW
BOW
FIVN
FIVN
Q1 26
$16.0M
Q4 25
$14.8M
Q3 25
$15.2M
$18.0M
Q2 25
$12.3M
$1.2M
Q1 25
$11.4M
$576.0K
Q4 24
Q3 24
$12.1M
$-4.5M
Q2 24
$5.5M
$-12.8M
Gross Margin
BOW
BOW
FIVN
FIVN
Q1 26
Q4 25
55.4%
Q3 25
55.0%
Q2 25
54.9%
Q1 25
55.0%
Q4 24
56.0%
Q3 24
53.8%
Q2 24
53.0%
Operating Margin
BOW
BOW
FIVN
FIVN
Q1 26
Q4 25
11.7%
6.6%
Q3 25
13.3%
5.6%
Q2 25
11.9%
-0.6%
Q1 25
11.8%
-1.9%
Q4 24
1.5%
Q3 24
13.5%
-5.8%
Q2 24
7.5%
-7.7%
Net Margin
BOW
BOW
FIVN
FIVN
Q1 26
10.3%
Q4 25
9.8%
Q3 25
10.5%
6.3%
Q2 25
9.3%
0.4%
Q1 25
9.3%
0.2%
Q4 24
Q3 24
10.4%
-1.7%
Q2 24
5.6%
-5.1%
EPS (diluted)
BOW
BOW
FIVN
FIVN
Q1 26
$0.48
Q4 25
$0.44
$0.22
Q3 25
$0.45
$0.21
Q2 25
$0.36
$0.01
Q1 25
$0.34
$0.01
Q4 24
$0.16
Q3 24
$0.36
$-0.06
Q2 24
$0.20
$-0.17

Balance Sheet & Financial Strength

Snapshot of each company's liquidity, leverage and book value from the latest quarter.

Metric
BOW
BOW
FIVN
FIVN
Cash + ST InvestmentsLiquidity on hand
$97.2M
$232.1M
Total DebtLower is stronger
Stockholders' EquityBook value
$457.9M
$785.8M
Total Assets
$2.5B
$1.8B
Debt / EquityLower = less leverage

8-quarter trend — quarters aligned by calendar period.

Cash + ST Investments
BOW
BOW
FIVN
FIVN
Q1 26
$97.2M
Q4 25
$193.5M
$232.1M
Q3 25
$197.9M
$193.4M
Q2 25
$114.8M
$205.5M
Q1 25
$88.0M
$370.3M
Q4 24
$362.5M
Q3 24
$132.9M
$291.0M
Q2 24
$180.3M
$175.7M
Total Debt
BOW
BOW
FIVN
FIVN
Q1 26
Q4 25
$146.4M
Q3 25
Q2 25
Q1 25
Q4 24
Q3 24
Q2 24
Stockholders' Equity
BOW
BOW
FIVN
FIVN
Q1 26
$457.9M
Q4 25
$448.3M
$785.8M
Q3 25
$430.2M
$775.3M
Q2 25
$407.2M
$717.4M
Q1 25
$391.0M
$664.3M
Q4 24
$622.2M
Q3 24
$364.7M
$565.6M
Q2 24
$339.9M
$525.9M
Total Assets
BOW
BOW
FIVN
FIVN
Q1 26
$2.5B
Q4 25
$2.4B
$1.8B
Q3 25
$2.1B
$1.8B
Q2 25
$1.9B
$1.7B
Q1 25
$1.8B
$2.1B
Q4 24
$2.1B
Q3 24
$1.5B
$2.0B
Q2 24
$1.4B
$1.9B
Debt / Equity
BOW
BOW
FIVN
FIVN
Q1 26
Q4 25
0.33×
Q3 25
Q2 25
Q1 25
Q4 24
Q3 24
Q2 24

Cash Flow & Capital Efficiency

How much cash each business actually produces after reinvestment. Cash flow is harder to manipulate than net income.

Metric
BOW
BOW
FIVN
FIVN
Operating Cash FlowLast quarter
$83.6M
Free Cash FlowOCF − Capex
$77.3M
FCF MarginFCF / Revenue
25.8%
Capex IntensityCapex / Revenue
2.1%
Cash ConversionOCF / Net Profit
TTM Free Cash FlowTrailing 4 quarters
$201.2M

8-quarter trend — quarters aligned by calendar period.

Operating Cash Flow
BOW
BOW
FIVN
FIVN
Q1 26
Q4 25
$331.6M
$83.6M
Q3 25
$114.7M
$59.2M
Q2 25
$109.0M
$35.1M
Q1 25
$47.7M
$48.4M
Q4 24
$49.8M
Q3 24
$119.4M
$41.1M
Q2 24
$19.9M
Free Cash Flow
BOW
BOW
FIVN
FIVN
Q1 26
Q4 25
$326.0M
$77.3M
Q3 25
$113.5M
$48.7M
Q2 25
$107.4M
$31.6M
Q1 25
$46.5M
$43.7M
Q4 24
$40.5M
Q3 24
$118.4M
$26.7M
Q2 24
$13.1M
FCF Margin
BOW
BOW
FIVN
FIVN
Q1 26
Q4 25
214.9%
25.8%
Q3 25
78.8%
17.0%
Q2 25
80.6%
11.1%
Q1 25
37.9%
15.6%
Q4 24
14.5%
Q3 24
101.4%
10.1%
Q2 24
5.2%
Capex Intensity
BOW
BOW
FIVN
FIVN
Q1 26
Q4 25
3.7%
2.1%
Q3 25
0.9%
3.7%
Q2 25
1.2%
1.2%
Q1 25
1.0%
1.7%
Q4 24
3.3%
Q3 24
0.9%
5.4%
Q2 24
2.7%
Cash Conversion
BOW
BOW
FIVN
FIVN
Q1 26
Q4 25
22.34×
Q3 25
7.56×
3.29×
Q2 25
8.83×
30.38×
Q1 25
4.18×
84.00×
Q4 24
Q3 24
9.88×
Q2 24

Financial Flow Comparison

Revenue → gross profit → operating profit → net profit for each company.

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