Skyward Specialty Insurance Group, Inc. (SKWD) AI Stock Analysis

• Market Cap: $1.88B
• Dividend Yield: N/A
• Average Volume (3M): 341.61K
• Price to Earnings (P/E): 13.8
• Beta (1Y): 0.41
• Revenue Growth: 22.51%
• EPS Growth: 2.19%
• Country: US
• Employees: 580
• Sector: Financial
• Sector Strength: 70
• Industry: Insurance - Property & Casualty
• EPS (TTM): 1.05
• Shares Outstanding: 40,487,366
• 10 Day Avg. Volume: 524,087
• 30 Day Avg. Volume: 341,609
• PEG Ratio: 0.64
• Price to Book (P/B): 2.55
• Price to Sales (P/S): 1.76
• P/FCF Ratio: 6.73
• Enterprise Value/Market Cap: 0.95
• Enterprise Value/Revenue: 1.33
• Enterprise Value/Gross Profit: 4.74
• Enterprise Value/Ebitda: 9.39
• 1Y Price Target: $65.83
• Price Target Upside: 41.63% Upside
• Rating Consensus: Strong Buy
• Number of Analyst Covering: 7
• EPS Forecast (FY): 4.75
• Revenue Forecast (FY): $2.66B

• Rating: 81 Outperform
• Price Target: $58.00 ▲(24.78% Upside)

The score is driven primarily by strong financial performance (solid profitability, low leverage, and robust cash generation). Supportive earnings-call results and strategic expansion via the Apollo acquisition add to the outlook, while the technical picture is only moderately positive (still below the 200-day average) and added leverage from deal financing tempers the upside.

Positive Factors

Sustained Profitability

Consistently positive net and EBIT margins indicate durable underwriting discipline and operating leverage across cycles. Margins near these levels support reinvestment and capital returns, and combined with a sub-90 combined ratio (89.2% Q3), suggest sustainable core profitability over the next several quarters.

Strong Cash Generation

Robust free cash flow growth and FCF roughly matching net income point to high earnings quality and internal funding capacity. This durable cash-generation ability supports premium growth, reinsurance costs, and strategic investments (including acquisitions) without immediate reliance on equity markets.

Strategic Market Expansion

Closing Apollo materially expands access to Lloyd’s and specialty markets, diversifying geographic and product exposure. This structural expansion increases distribution channels and cross-sell potential, improving long-term growth optionality and resilience to regional underwriting cycles.

Negative Factors

Higher Post-Deal Leverage

Rising leverage to roughly 28% from a previously conservative base meaningfully increases financial risk and interest-cost sensitivity. Higher leverage can constrain capital allocation, tighten covenant headroom from new term loans, and reduce flexibility during underwriting or investment stress periods.

Decelerating Growth & Data Gaps

Slowing revenue growth versus prior high-pace years reduces the runway for operating leverage and EPS expansion. Inconsistent gross margin reporting limits confidence in trend forecasts, complicating pricing, reserve-setting and long-range underwriting strategy across volatile lines.

Underwriting & Investment Volatility

Rising auto liability severity and inflationary loss trends increase claims cost risk across exposed segments, pressuring combined ratios if not offset by pricing/reinsurance. Coupled with investment income marks on alternatives, this raises structural volatility in earnings and capital adequacy over multiple quarters.

Skyward Specialty Insurance Group, Inc. Business Overview & Revenue Model

Company Description

Skyward Specialty Insurance Group, Inc., an insurance holding company, engages in underwriting commercial property and casualty insurance coverages in the United States. The company offers general liability, excess liability, professional liability, commercial auto, group accident and health, property, surety, and workers' compensation insurance products. Skyward Specialty Insurance Group, Inc. was incorporated in 2006 and is headquartered in Houston, Texas.

How the Company Makes Money

Skyward Specialty Insurance Group generates revenue primarily through the underwriting of insurance policies. The company collects premiums from policyholders in exchange for coverage against specific risks. Key revenue streams include premiums from property and casualty insurance, specialty insurance products, and risk management services. Additionally, SKWD may earn investment income from its reserves and surplus funds, which are allocated in various investment instruments. Strategic partnerships with brokers and agents also enhance their distribution channels, facilitating wider reach and penetration into niche markets, contributing to overall revenue growth.

Skyward Specialty Insurance Group, Inc. Financial Statement Overview

Summary

Strong overall fundamentals: improving scale, stable profitability (net margin ~10%, EBIT margin ~14% in 2024/TTM), low leverage (debt-to-equity ~0.12 TTM), and robust cash generation with TTM FCF up ~35% and good earnings quality. Main offsets are decelerating revenue growth and a few reported metric inconsistencies (gross margin history and a TTM coverage ratio).

Income Statement

SKWD shows strong top-line momentum and improving profitability. Revenue expanded meaningfully from 2021–2024, and TTM (Trailing-Twelve-Months) revenue is up ~6% versus the prior year, while net margins have held around ~10% in 2024 and TTM. Operating profitability is solid and stable (EBIT margin ~14% in both 2024 and TTM), a clear improvement versus earlier years and a major turnaround from the 2020 loss. Main weakness: growth is decelerating versus the very high 2022–2023 pace, and gross margin data appears inconsistent across years (limits confidence in that specific line item trend).

Balance Sheet

The balance sheet looks conservatively levered with low debt relative to equity (debt-to-equity ~0.12 in TTM (Trailing-Twelve-Months), improving from ~0.31 in 2021–2022). Equity has grown steadily alongside rising assets, and profitability on equity is strong (ROE ~15% in 2024 and ~16% in TTM). Key risk to watch is that total assets have scaled quickly over time, which can increase sensitivity to underwriting/investment cycles, but leverage metrics remain supportive.

Cash Flow

Cash generation is a clear strength: operating cash flow and free cash flow are both robust and have grown alongside earnings, with TTM (Trailing-Twelve-Months) free cash flow up ~35%. Free cash flow closely tracks net income (near 1.0x in 2024 and TTM), suggesting good earnings quality. Weakness: cash flow growth has been somewhat volatile year-to-year (including a decline in 2024), and the TTM operating cash flow coverage ratio is reported as 0.0, which appears inconsistent with the other cash flow figures and reduces confidence in that specific indicator.

Breakdown	TTM	Dec 2024	Dec 2023	Dec 2022	Dec 2021	Dec 2020
Income Statement
Total Revenue	1.34B	1.15B	895.40M	636.40M	535.82M	447.89M
Gross Profit	376.23M	327.89M	271.65M	168.20M	134.35M	48.73M
EBITDA	190.12M	165.59M	124.02M	60.29M	58.53M	-83.02M
Net Income	141.20M	118.83M	85.98M	39.40M	38.32M	-74.64M
Balance Sheet
Total Assets	4.59B	3.73B	2.95B	2.36B	2.12B	487.16M
Cash, Cash Equivalents and Short-Term Investments	1.48B	1.18B	1.35B	774.17M	664.74M	74.85M
Total Debt	119.56M	119.54M	128.69M	128.61M	128.53M	32.11M
Total Liabilities	3.63B	2.94B	2.29B	1.94B	1.69B	411.35M
Stockholders Equity	961.42M	794.00M	661.03M	421.66M	426.08M	75.81M
Cash Flow
Free Cash Flow	371.38M	300.89M	335.03M	206.61M	173.13M	42.64M
Operating Cash Flow	378.21M	305.12M	338.19M	208.94M	175.28M	44.71M
Investing Cash Flow	-331.30M	-243.69M	-493.81M	-193.38M	-183.01M	-74.93M
Financing Cash Flow	1.00K	-4.23M	130.95M	2.18M	1.38M	56.30M

Skyward Specialty Insurance Group, Inc. Technical Analysis

• Technical Analysis Sentiment: Negative
• Last Price: 46.48
• 50DMA: Negative
• 100DMA: Negative
• 200DMA: Negative
• MACD: Positive
• RSI: Neutral
• STOCH: Neutral

Evaluating momentum and price trends is crucial in stock analysis to make informed investment decisions. For SKWD, the sentiment is Negative. The current price of 46.48 is below the 20-day moving average (MA) of 49.09, below the 50-day MA of 48.40, and below the 200-day MA of 51.58, indicating a bearish trend. The MACD of -0.86 indicates Positive momentum. The RSI at 42.72 is Neutral, neither overbought nor oversold. The STOCH value of 22.98 is Neutral, not indicating any strong overbought or oversold conditions. Overall, these indicators collectively point to a Negative sentiment for SKWD.

Skyward Specialty Insurance Group, Inc. Peers Comparison

Name	Overall Rating	Market Cap	P/E Ratio	ROE	Dividend Yield	Revenue Growth	EPS Growth
SKWD	81 Outperform	$1.88B	13.76	16.06%	―	22.51%	2.19%
HCI	78 Outperform	$2.28B	11.23	31.94%	0.82%	8.71%	17.26%
SAFT	75 Outperform	$1.13B	12.92	9.97%	4.59%	13.35%	16.56%
STC	74 Outperform	$1.98B	18.38	7.08%	2.88%	16.22%	69.80%
SLDE	73 Outperform	$2.02B	1.50	52.29%	―	―	―
ROOT	70 Neutral	$1.09B	22.50	17.02%	―	38.50%	―
Sector *	68 Neutral	$18.00B	11.42	9.92%	3.81%	9.73%	1.22%

Skyward Specialty Insurance Group, Inc. Corporate Events

Skyward Specialty Completes Apollo Acquisition and Equity Issuance

On December 30, 2025, Skyward Specialty entered into a new unsecured senior delayed draw term loan facility totaling $300 million, split between Tranche A maturing January 1, 2028 and Tranche B maturing July 2, 2029, with pricing tied to term SOFR or a base rate plus a margin, and customary covenants on leverage, capital, ratings and liquidity, as well as a related guaranty from most non-insurance subsidiaries and an amendment to its existing credit agreement to permit pre-funding of revolving loans. Using proceeds from this new facility and its existing credit agreement, the company completed the previously announced acquisition of U.K.-based Apollo Group Holdings Limited on the January 2, 2026 closing date, paying roughly $555 million through $371 million in cash and the issuance of 3.68 million common shares, a move that expands Skyward Specialty’s presence at Lloyd’s of London and broadens its product and geographic reach in specialty insurance markets.

The most recent analyst rating on (SKWD) stock is a Buy with a $69.00 price target. To see the full list of analyst forecasts on Skyward Specialty Insurance Group, Inc. stock, see the SKWD Stock Forecast page.

Skyward Specialty Gets Approval for Apollo Acquisition

On December 3, 2025, Skyward Specialty Insurance Group, Inc. announced it has received regulatory and minority shareholder approvals for its acquisition of Apollo Group Holdings Limited, with the transaction expected to close in early 2026. The company also provided its 2026 financial guidance, projecting significant growth in gross written premiums, net income, and adjusted operating income, reflecting the anticipated impact of the Apollo acquisition and its commitment to delivering top quartile results.

The most recent analyst rating on (SKWD) stock is a Buy with a $64.00 price target. To see the full list of analyst forecasts on Skyward Specialty Insurance Group, Inc. stock, see the SKWD Stock Forecast page.

Skyward Specialty Enters New $150M Credit Agreement

On November 13, 2025, Skyward Specialty Insurance Group, Inc. entered into a new Credit Agreement with a revolving loan facility initially set at $150 million, which will increase to $250 million upon the closing of its acquisition of Apollo Group Holdings Limited. The agreement includes provisions for letters of credit and an uncommitted accordion feature for additional financing, with interest rates tied to the company’s debt to capitalization ratio. Concurrently, the company terminated its previous credit agreement from March 28, 2023, fully repaying all outstanding amounts.

The most recent analyst rating on (SKWD) stock is a Buy with a $64.00 price target. To see the full list of analyst forecasts on Skyward Specialty Insurance Group, Inc. stock, see the SKWD Stock Forecast page.

Skyward Specialty Appoints Christopher Peirce to Board

Skyward Specialty Insurance Group, Inc. announced the appointment of Christopher Peirce to its Board of Directors, effective February 1, 2026. Peirce, with 30 years of experience at Liberty Mutual Insurance, is expected to bring significant financial and strategic expertise to the board, particularly as the company anticipates the closure of the Apollo acquisition in early 2026. Additionally, Peirce is set to become the Chair of the Audit Committee after the 2025 financial year, succeeding Robert Creager, who will not seek re-election after his term ends in May.

The most recent analyst rating on (SKWD) stock is a Buy with a $64.00 price target. To see the full list of analyst forecasts on Skyward Specialty Insurance Group, Inc. stock, see the SKWD Stock Forecast page.