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Upturn AI Summary - About
Skyward Specialty Insurance Group, Inc. Common Stock(SKWD)
Advisory History & Simulated Performance *
*as per simulation (see disclosures)- ALL
- 1Y
- 1M
- 1W
- BUY Advisory
- SELL Advisory (Profit)
- SELL Advisory (Loss)
- Profit
- Loss
- PASS (Skip)
Stock price based on last close Advisory Performance History (Simulated)
Upturn Advisory & Investor View for SKWD
11/02/2026: SKWD (2-star) has a low Upturn Star Rating. Not recommended to BUY.
Skyward Specialty Insurance Group is a focused specialty insurer that operates in complex, niche commercial markets. By emphasizing disciplined underwriting and tech-enabled service, the company has established a credible market position within the excess and surplus lines sector. The primary growth opportunity lies in its ability to expand into additional underserved niches while maintaining high underwriting margins. However, investors face risks related to intense competition from larger insurers, potential catastrophe losses, and the inherent volatility of insurance markets. This stock is primarily suited for growth-oriented investors who are comfortable with the risks of a mid-cap specialty financial firm; developments to monitor include premium growth and underwriting performance ratios.
How to Read the Upturn Advisory
The Upturn Star Rating and the current BUY, SELL, or PASS advisory are generated by Upturn’s AI advisory engine based on proprietary signal analysis, price behavior, advisory history, and historical signal performance.
Company fundamentals, valuation, risks, and news provide supporting context about the business.
Investor Fit
| Investor style | Fit | Why |
|---|---|---|
| Growth investor | Strong fit | The company is in a high-growth phase within the specialty insurance market, targeting significant scale. |
| Momentum investor | Strong fit while signal remains positive | The stock has demonstrated consistent upward momentum, making it attractive to trend-following strategies. |
| Value investor | Mixed fit | As a growth-stage company, it often commands a premium valuation that may not satisfy traditional value investors. |
| Dividend investor | Weak fit | The company currently does not pay a regular dividend, prioritizing capital growth over income. |
| Low-risk investor | Weak fit | The insurance sector involves inherent volatility and execution risk not suitable for low-risk portfolios. |
Risk Profile
| Risk factor | Level | Why it matters |
|---|---|---|
| Price volatility | Medium / high | As a growth-oriented mid-cap stock, price swings can be significant based on market sentiment. |
| Valuation risk | Medium | High growth expectations are priced into the stock, leaving little margin for earnings misses. |
| Competition risk | Medium / high | Intense competition from established players like RLI and KNSL limits pricing power. |
| Business quality | Medium / high | Strong underwriting discipline supports business quality, though it remains tested by industry cycles. |
| Dividend income | Low / none | Investors should not expect income; this stock is strictly for capital appreciation. |
| Execution risk | Medium | Success depends on the continued ability to price and underwrite risks effectively in new niches. |
Price Behavior
Strong Uptrend
The stock has maintained a strong upward price trend across the last three quarters.
Moderately Choppy
The stock has experienced noticeable price swings while retaining some directional structure.
Analysis of Past Performance
Type Stock | Historic Profit 11.43% | Avg. Invested days 40 | Today’s Advisory Consider higher Upturn Star rating |
Upturn Advisory Rating  | Upturn Advisory Performance  3.0 | Stock Returns Performance  2.0 |
| Profits based on simulation | Last Close 11/02/2026 |
Upturn Scorecard
Upturn Star Rating 
Company Fundamentals
Financial Health Rating
Growth Momentum Score
Ownership
Top 5 Institutional Investors
Unit Economics (Per $1K Revenue)
Economic Dimensions
Quantitative Style Profile
Style Classification
Quality Focused
Key Highlights
Company Size Mid-Cap Stock | Market Capitalization 2.71B USD | Price to earnings Ratio 14.18 | 1Y Target Price 70.73 |
Price to earnings Ratio 14.18 | 1Y Target Price 70.73 | ||
Volume (30-day avg) 339.1K shares | Beta 0.31 | 52 Weeks Range 40.60 - 65.69 | Updated Date 11/02/2026 |
52 Weeks Range 40.60 - 65.69 | Updated Date 11/02/2026 | ||
Dividends yield (FY) - | Basic EPS (TTM) 4.31 |
How Company Makes Money
| Business area | What it includes | Retail investor read |
|---|---|---|
| Underwriting Premiums | Premiums collected for commercial property, liability, and specialty accident products. | The company makes money by collecting more in premiums than it pays out in claims and operating costs. |
| Net Investment Income | Interest and dividends earned on the company's investment portfolio of float. | The firm earns additional income by safely investing the cash held to pay future insurance claims. |
Earnings Date
Report Date 2026-11-05 | When After Market | Estimate 1.22 | Actual - |
Profitability
Profit Margin 10.84% | Operating Margin (TTM) 14.78% |
Management Effectiveness
Return on Assets (TTM) 3.1% | Return on Equity (TTM) 17.34% |
Valuation
Trailing PE 14.18 | Forward PE 10.66 | Enterprise Value 2.84B | Price to Sales(TTM) 1.57 |
Enterprise Value 2.84B | Price to Sales(TTM) 1.57 | ||
Enterprise Value to Revenue 1.64 | Enterprise Value to EBITDA - | Shares Outstanding 44.40M | Shares Floating 40.49M |
Shares Outstanding 44.40M | Shares Floating 40.49M | ||
Percent Insiders 8.18 | Percent Institutions 94.29 |
Financial Metrics
🧭 Investment Snapshot
Total Revenue (Scale)
Total money earned from selling products or services before any costs. It is needed to understand the scale of the business and its ability to generate income.
Net Income (Profit)
Final profit after all expenses, interest, and taxes are deducted. It is needed to determine the overall profitability available to shareholders.
Free Cash Flow (Cash Strength)
Cash remaining after operating activities and capital expenditures, showing cash available for growth. It is needed to evaluate the company’s ability to invest, pay dividends, or reduce debt.
📈 Growth & Strength
Operating Income (Core Profit)
Profit from core operations after deducting all operating expenses. It is needed to measure how efficiently the company runs its primary business activities.
EBITDA (Cash Earnings)
Earnings before interest, taxes, depreciation, and amortization, indicating operating cash potential. It is needed to compare operating performance across companies without accounting or financing differences.
Gross Profit (Unit Profitability)
Revenue minus cost of revenue, showing profit after direct production costs. It is needed to evaluate core business profitability before overhead expenses.
🛡️ Financial Safety
Cash (Liquidity Buffer)
Total cash and cash equivalents on hand. It is needed to evaluate immediate liquidity and financial flexibility.
Total Debt (Leverage Risk)
Total debt including both short-term and long-term components. It is needed to assess the company’s leverage and financial risk.
Net Working Capital (Short-Term Health)
Current assets minus current liabilities, indicating short-term liquidity strength. It is needed to assess whether the company can meet its short-term obligations.
🧱 Balance Sheet Strength
Stockholder Equity (Net Worth)
Total equity value held by shareholders. It is needed to understand the net worth of the company from the owners’ perspective.
Total Assets (Asset Base)
The full value of everything the company owns, including cash, inventory, equipment, and investments. It is needed to understand the resource base used to generate revenue.
Income Before Tax (Pre-Tax Earnings)
Income before provision for income taxes. It is needed to analyze profitability independent of tax structures.
⚙️ Cost & Drag Factors
Cost of Revenue (Production Cost)
Direct costs required to produce and deliver the products or services sold. It is needed to assess efficiency in production and service delivery.
Total Operating Expenses (Operating Cost)
Indirect costs of running the business such as salaries, marketing, and administration. It is needed to understand how much it costs to sustain ongoing business operations.
Income Tax Expense (Tax Drag)
Amount of taxes paid or payable to the government. It is needed to evaluate the impact of taxation on overall profitability.
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