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Side-by-side financial comparison of Skyward Specialty Insurance Group, Inc. (SKWD) and Waystar Holding Corp. (WAY). Click either name above to swap in a different company.
Skyward Specialty Insurance Group, Inc. is the larger business by last-quarter revenue ($385.6M vs $313.9M, roughly 1.2× Waystar Holding Corp.). Waystar Holding Corp. runs the higher net margin — 13.8% vs 11.2%, a 2.6% gap on every dollar of revenue. On growth, Skyward Specialty Insurance Group, Inc. posted the faster year-over-year revenue change (26.7% vs 22.4%). Skyward Specialty Insurance Group, Inc. produced more free cash flow last quarter ($402.6M vs $90.3M). Over the past eight quarters, Skyward Specialty Insurance Group, Inc.'s revenue compounded faster (20.6% CAGR vs 15.7%).
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.
Waystar Holding Corp is a leading provider of integrated healthcare payment and revenue cycle management solutions. It serves healthcare providers, health systems, and payers across the United States, offering tools that streamline billing, claims processing, patient payment collection, and revenue optimization to reduce administrative burdens and improve financial performance for healthcare organizations.
SKWD vs WAY — Head-to-Head
Income Statement — Q4 FY2025 vs Q1 FY2026
| Metric | | |
|---|---|---|
| Revenue | $385.6M | $313.9M |
| Net Profit | $43.2M | $43.3M |
| Gross Margin | — | — |
| Operating Margin | 14.2% | 25.6% |
| Net Margin | 11.2% | 13.8% |
| Revenue YoY | 26.7% | 22.4% |
| Net Profit YoY | 200.1% | 47.9% |
| EPS (diluted) | $1.03 | $0.42 |
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.
| Q1 26 | — | $313.9M | ||
| Q4 25 | $385.6M | $303.5M | ||
| Q3 25 | $382.5M | $268.7M | ||
| Q2 25 | $319.9M | $270.7M | ||
| Q1 25 | $328.5M | $256.4M | ||
| Q4 24 | $304.4M | $244.1M | ||
| Q3 24 | $300.9M | $240.1M | ||
| Q2 24 | $279.9M | $234.5M |
| Q1 26 | — | $43.3M | ||
| Q4 25 | $43.2M | $20.0M | ||
| Q3 25 | $45.9M | $30.6M | ||
| Q2 25 | $38.8M | $32.2M | ||
| Q1 25 | $42.1M | $29.3M | ||
| Q4 24 | $14.4M | $19.1M | ||
| Q3 24 | $36.7M | $5.4M | ||
| Q2 24 | $31.0M | $-27.7M |
| Q1 26 | — | 25.6% | ||
| Q4 25 | 14.2% | 19.4% | ||
| Q3 25 | 15.8% | 22.4% | ||
| Q2 25 | 15.6% | 24.0% | ||
| Q1 25 | 15.7% | 25.4% | ||
| Q4 24 | 6.1% | 21.8% | ||
| Q3 24 | 15.6% | 11.3% | ||
| Q2 24 | 14.4% | 3.5% |
| Q1 26 | — | 13.8% | ||
| Q4 25 | 11.2% | 6.6% | ||
| Q3 25 | 12.0% | 11.4% | ||
| Q2 25 | 12.1% | 11.9% | ||
| Q1 25 | 12.8% | 11.4% | ||
| Q4 24 | 4.7% | 7.8% | ||
| Q3 24 | 12.2% | 2.3% | ||
| Q2 24 | 11.1% | -11.8% |
| Q1 26 | — | $0.42 | ||
| Q4 25 | $1.03 | $0.10 | ||
| Q3 25 | $1.10 | $0.17 | ||
| Q2 25 | $0.93 | $0.18 | ||
| Q1 25 | $1.01 | $0.16 | ||
| Q4 24 | $0.33 | $0.18 | ||
| Q3 24 | $0.89 | $0.03 | ||
| Q2 24 | $0.75 | $-0.21 |
Balance Sheet & Financial Strength
Snapshot of each company's liquidity, leverage and book value from the latest quarter.
| Metric | | |
|---|---|---|
| Cash + ST InvestmentsLiquidity on hand | $168.5M | $34.3M |
| Total DebtLower is stronger | — | $13.5M |
| Stockholders' EquityBook value | $1.0B | $3.9B |
| Total Assets | $4.8B | $5.8B |
| Debt / EquityLower = less leverage | — | 0.00× |
8-quarter trend — quarters aligned by calendar period.
| Q1 26 | — | $34.3M | ||
| Q4 25 | $168.5M | $61.4M | ||
| Q3 25 | $160.1M | $421.1M | ||
| Q2 25 | $136.6M | $290.3M | ||
| Q1 25 | $112.9M | $224.0M | ||
| Q4 24 | $121.6M | $182.1M | ||
| Q3 24 | $105.6M | $127.1M | ||
| Q2 24 | $73.0M | $68.4M |
| Q1 26 | — | $13.5M | ||
| Q4 25 | — | $1.5B | ||
| Q3 25 | — | — | ||
| Q2 25 | — | — | ||
| Q1 25 | — | — | ||
| Q4 24 | — | $1.2B | ||
| Q3 24 | — | — | ||
| Q2 24 | — | — |
| Q1 26 | — | $3.9B | ||
| Q4 25 | $1.0B | $3.9B | ||
| Q3 25 | $961.4M | $3.2B | ||
| Q2 25 | $899.9M | $3.2B | ||
| Q1 25 | $850.7M | $3.1B | ||
| Q4 24 | $794.0M | $3.1B | ||
| Q3 24 | $797.5M | $3.1B | ||
| Q2 24 | $723.6M | $2.9B |
| Q1 26 | — | $5.8B | ||
| Q4 25 | $4.8B | $5.8B | ||
| Q3 25 | $4.6B | $4.7B | ||
| Q2 25 | $4.3B | $4.7B | ||
| Q1 25 | $4.0B | $4.6B | ||
| Q4 24 | $3.7B | $4.6B | ||
| Q3 24 | $3.6B | $4.5B | ||
| Q2 24 | $3.4B | $4.6B |
| Q1 26 | — | 0.00× | ||
| Q4 25 | — | 0.38× | ||
| Q3 25 | — | — | ||
| Q2 25 | — | — | ||
| Q1 25 | — | — | ||
| Q4 24 | — | 0.40× | ||
| 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 | | |
|---|---|---|
| Operating Cash FlowLast quarter | $408.1M | $84.9M |
| Free Cash FlowOCF − Capex | $402.6M | $90.3M |
| FCF MarginFCF / Revenue | 104.4% | 28.8% |
| Capex IntensityCapex / Revenue | 1.4% | — |
| Cash ConversionOCF / Net Profit | 9.44× | 1.96× |
| TTM Free Cash FlowTrailing 4 quarters | $755.2M | $314.6M |
8-quarter trend — quarters aligned by calendar period.
| Q1 26 | — | $84.9M | ||
| Q4 25 | $408.1M | $66.6M | ||
| Q3 25 | $171.4M | $82.0M | ||
| Q2 25 | $88.2M | $96.8M | ||
| Q1 25 | $96.8M | $64.2M | ||
| Q4 24 | $305.1M | — | ||
| Q3 24 | $168.0M | $78.8M | ||
| Q2 24 | $21.0M | $15.4M |
| Q1 26 | — | $90.3M | ||
| Q4 25 | $402.6M | $57.2M | ||
| Q3 25 | $168.9M | $76.2M | ||
| Q2 25 | $87.1M | $91.0M | ||
| Q1 25 | $96.6M | $58.8M | ||
| Q4 24 | $300.9M | — | ||
| Q3 24 | $167.6M | $70.2M | ||
| Q2 24 | $18.4M | $8.6M |
| Q1 26 | — | 28.8% | ||
| Q4 25 | 104.4% | 18.9% | ||
| Q3 25 | 44.2% | 28.3% | ||
| Q2 25 | 27.2% | 33.6% | ||
| Q1 25 | 29.4% | 22.9% | ||
| Q4 24 | 98.8% | — | ||
| Q3 24 | 55.7% | 29.2% | ||
| Q2 24 | 6.6% | 3.7% |
| Q1 26 | — | — | ||
| Q4 25 | 1.4% | 3.1% | ||
| Q3 25 | 0.6% | 2.2% | ||
| Q2 25 | 0.3% | 2.1% | ||
| Q1 25 | 0.1% | 2.1% | ||
| Q4 24 | 1.4% | — | ||
| Q3 24 | 0.1% | 3.6% | ||
| Q2 24 | 0.9% | 2.9% |
| Q1 26 | — | 1.96× | ||
| Q4 25 | 9.44× | 3.33× | ||
| Q3 25 | 3.73× | 2.68× | ||
| Q2 25 | 2.27× | 3.01× | ||
| Q1 25 | 2.30× | 2.20× | ||
| Q4 24 | 21.18× | — | ||
| Q3 24 | 4.58× | 14.56× | ||
| Q2 24 | 0.68× | — |
Financial Flow Comparison
Revenue → gross profit → operating profit → net profit for each company.
Revenue Breakdown by Segment
SKWD
Segment breakdown not available.
WAY
| Subscription | $172.2M | 55% |
| Volume-based | $139.5M | 44% |
