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Side-by-side financial comparison of Skyward Specialty Insurance Group, Inc. (SKWD) and Tyler Technologies (TYL). Click either name above to swap in a different company.

Tyler Technologies is the larger business by last-quarter revenue ($613.5M vs $385.6M, roughly 1.6× Skyward Specialty Insurance Group, Inc.). Tyler Technologies runs the higher net margin — 13.2% vs 11.2%, a 2.0% gap on every dollar of revenue. On growth, Skyward Specialty Insurance Group, Inc. posted the faster year-over-year revenue change (26.7% vs 8.6%). Skyward Specialty Insurance Group, Inc. produced more free cash flow last quarter ($402.6M vs $2.0M). Over the past eight quarters, Skyward Specialty Insurance Group, Inc.'s revenue compounded faster (20.6% CAGR vs 6.5%).

Skyward Specialty Insurance Group, Inc. is a specialty property and casualty insurance provider offering tailored coverage solutions including commercial auto, general liability, professional indemnity, and specialty property policies. It primarily serves small-to-medium enterprises and niche industry segments across the United States, focusing on underwriting complex, hard-to-place risks for underserved client groups.

Tyler Technologies, Inc. is an American technology company based in Plano, Texas, that provides proprietary software to the U.S. public sector. Tyler Technologies has offices in 17 states and one in Toronto, Ontario, Canada.

SKWD vs TYL — Head-to-Head

Bigger by revenue
TYL
TYL
1.6× larger
TYL
$613.5M
$385.6M
SKWD
Growing faster (revenue YoY)
SKWD
SKWD
+18.1% gap
SKWD
26.7%
8.6%
TYL
Higher net margin
TYL
TYL
2.0% more per $
TYL
13.2%
11.2%
SKWD
More free cash flow
SKWD
SKWD
$400.6M more FCF
SKWD
$402.6M
$2.0M
TYL
Faster 2-yr revenue CAGR
SKWD
SKWD
Annualised
SKWD
20.6%
6.5%
TYL

Income Statement — Q4 FY2025 vs Q1 FY2026

Metric
SKWD
SKWD
TYL
TYL
Revenue
$385.6M
$613.5M
Net Profit
$43.2M
$81.2M
Gross Margin
48.3%
Operating Margin
14.2%
16.3%
Net Margin
11.2%
13.2%
Revenue YoY
26.7%
8.6%
Net Profit YoY
200.1%
EPS (diluted)
$1.03
$1.88

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
SKWD
SKWD
TYL
TYL
Q1 26
$613.5M
Q4 25
$385.6M
$575.2M
Q3 25
$382.5M
$595.9M
Q2 25
$319.9M
$596.1M
Q1 25
$328.5M
$565.2M
Q4 24
$304.4M
$541.1M
Q3 24
$300.9M
$543.3M
Q2 24
$279.9M
$541.0M
Net Profit
SKWD
SKWD
TYL
TYL
Q1 26
$81.2M
Q4 25
$43.2M
$65.5M
Q3 25
$45.9M
$84.4M
Q2 25
$38.8M
$84.6M
Q1 25
$42.1M
$81.1M
Q4 24
$14.4M
$65.2M
Q3 24
$36.7M
$75.9M
Q2 24
$31.0M
$67.7M
Gross Margin
SKWD
SKWD
TYL
TYL
Q1 26
48.3%
Q4 25
45.5%
Q3 25
47.2%
Q2 25
45.8%
Q1 25
47.3%
Q4 24
43.8%
Q3 24
43.7%
Q2 24
44.0%
Operating Margin
SKWD
SKWD
TYL
TYL
Q1 26
16.3%
Q4 25
14.2%
13.0%
Q3 25
15.8%
16.4%
Q2 25
15.6%
16.0%
Q1 25
15.7%
15.8%
Q4 24
6.1%
13.2%
Q3 24
15.6%
15.2%
Q2 24
14.4%
14.4%
Net Margin
SKWD
SKWD
TYL
TYL
Q1 26
13.2%
Q4 25
11.2%
11.4%
Q3 25
12.0%
14.2%
Q2 25
12.1%
14.2%
Q1 25
12.8%
14.3%
Q4 24
4.7%
12.1%
Q3 24
12.2%
14.0%
Q2 24
11.1%
12.5%
EPS (diluted)
SKWD
SKWD
TYL
TYL
Q1 26
$1.88
Q4 25
$1.03
$1.50
Q3 25
$1.10
$1.93
Q2 25
$0.93
$1.93
Q1 25
$1.01
$1.84
Q4 24
$0.33
$1.48
Q3 24
$0.89
$1.74
Q2 24
$0.75
$1.57

Balance Sheet & Financial Strength

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

Metric
SKWD
SKWD
TYL
TYL
Cash + ST InvestmentsLiquidity on hand
$168.5M
$346.4M
Total DebtLower is stronger
Stockholders' EquityBook value
$1.0B
$3.6B
Total Assets
$4.8B
$4.8B
Debt / EquityLower = less leverage

8-quarter trend — quarters aligned by calendar period.

Cash + ST Investments
SKWD
SKWD
TYL
TYL
Q1 26
$346.4M
Q4 25
$168.5M
$1.1B
Q3 25
$160.1M
$950.8M
Q2 25
$136.6M
$892.3M
Q1 25
$112.9M
$807.4M
Q4 24
$121.6M
$768.0M
Q3 24
$105.6M
$544.3M
Q2 24
$73.0M
$258.0M
Total Debt
SKWD
SKWD
TYL
TYL
Q1 26
Q4 25
$599.7M
Q3 25
$599.2M
Q2 25
$598.8M
Q1 25
$598.4M
Q4 24
$597.9M
Q3 24
$597.5M
Q2 24
$597.1M
Stockholders' Equity
SKWD
SKWD
TYL
TYL
Q1 26
$3.6B
Q4 25
$1.0B
$3.7B
Q3 25
$961.4M
$3.6B
Q2 25
$899.9M
$3.6B
Q1 25
$850.7M
$3.5B
Q4 24
$794.0M
$3.4B
Q3 24
$797.5M
$3.3B
Q2 24
$723.6M
$3.1B
Total Assets
SKWD
SKWD
TYL
TYL
Q1 26
$4.8B
Q4 25
$4.8B
$5.6B
Q3 25
$4.6B
$5.5B
Q2 25
$4.3B
$5.4B
Q1 25
$4.0B
$5.2B
Q4 24
$3.7B
$5.2B
Q3 24
$3.6B
$5.0B
Q2 24
$3.4B
$4.8B
Debt / Equity
SKWD
SKWD
TYL
TYL
Q1 26
Q4 25
0.16×
Q3 25
0.17×
Q2 25
0.16×
Q1 25
0.17×
Q4 24
0.18×
Q3 24
0.18×
Q2 24
0.19×

Cash Flow & Capital Efficiency

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

Metric
SKWD
SKWD
TYL
TYL
Operating Cash FlowLast quarter
$408.1M
$107.3M
Free Cash FlowOCF − Capex
$402.6M
$2.0M
FCF MarginFCF / Revenue
104.4%
0.3%
Capex IntensityCapex / Revenue
1.4%
Cash ConversionOCF / Net Profit
9.44×
1.32×
TTM Free Cash FlowTrailing 4 quarters
$755.2M
$585.7M

8-quarter trend — quarters aligned by calendar period.

Operating Cash Flow
SKWD
SKWD
TYL
TYL
Q1 26
$107.3M
Q4 25
$408.1M
$243.9M
Q3 25
$171.4M
$255.2M
Q2 25
$88.2M
$98.3M
Q1 25
$96.8M
$56.2M
Q4 24
$305.1M
$224.8M
Q3 24
$168.0M
$263.7M
Q2 24
$21.0M
$64.3M
Free Cash Flow
SKWD
SKWD
TYL
TYL
Q1 26
$2.0M
Q4 25
$402.6M
$239.6M
Q3 25
$168.9M
$251.3M
Q2 25
$87.1M
$92.8M
Q1 25
$96.6M
$53.8M
Q4 24
$300.9M
$221.0M
Q3 24
$167.6M
$260.8M
Q2 24
$18.4M
$57.7M
FCF Margin
SKWD
SKWD
TYL
TYL
Q1 26
0.3%
Q4 25
104.4%
41.7%
Q3 25
44.2%
42.2%
Q2 25
27.2%
15.6%
Q1 25
29.4%
9.5%
Q4 24
98.8%
40.8%
Q3 24
55.7%
48.0%
Q2 24
6.6%
10.7%
Capex Intensity
SKWD
SKWD
TYL
TYL
Q1 26
Q4 25
1.4%
0.8%
Q3 25
0.6%
0.7%
Q2 25
0.3%
0.9%
Q1 25
0.1%
0.4%
Q4 24
1.4%
0.7%
Q3 24
0.1%
0.5%
Q2 24
0.9%
1.2%
Cash Conversion
SKWD
SKWD
TYL
TYL
Q1 26
1.32×
Q4 25
9.44×
3.72×
Q3 25
3.73×
3.02×
Q2 25
2.27×
1.16×
Q1 25
2.30×
0.69×
Q4 24
21.18×
3.45×
Q3 24
4.58×
3.47×
Q2 24
0.68×
0.95×

Financial Flow Comparison

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

Revenue Breakdown by Segment

SKWD
SKWD

Segment breakdown not available.

TYL
TYL

Subscriptions$429.7M70%
Maintenance$108.9M18%
Other$74.9M12%

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