Skyward Finalizes $555M Apollo Deal, Securing Key Lloyd's Market Access

HOUSTON, TX – January 02, 2026 – Skyward Specialty Insurance Group, Inc. has officially completed its acquisition of Apollo Group Holdings Limited, a significant strategic maneuver that provides the Houston-based insurer with a coveted and direct presence in the prestigious Lloyd's of London market. The deal, valued at $555 million, was finalized today under the terms previously agreed upon when the definitive agreement was announced on September 2, 2025.

This acquisition marks a pivotal moment for Skyward Specialty (Nasdaq: SKWD), a rapidly growing commercial property and casualty insurer. By integrating Apollo, a UK-based, innovation-focused insurance platform, Skyward not only expands its geographic footprint but also significantly enhances its technological capabilities and specialty product offerings. The move is expected to be immediately accretive to Skyward's earnings, signaling strong confidence from leadership and a positive outlook from market analysts who see substantial upside potential in the combined entity.

A Strategic Leap into the Lloyd's Market

The cornerstone of this acquisition is the immediate and influential access it grants Skyward Specialty to the world's leading insurance marketplace, Lloyd's of London. While technically a UK subsidiary, Apollo has operated as a US-focused specialty underwriting platform within Lloyd's, making it a uniquely synergistic fit for Skyward. This integration is a core component of Skyward's 'Rule Our Niche' strategy, which focuses on deepening expertise in high-margin specialty lines.

Through Apollo's Syndicate 1969, Skyward gains entry into attractive and hard-to-reach specialty classes, including Political Violence, Product Recall, and Specialty Disruption. This diversifies Skyward's portfolio beyond its existing nine underwriting divisions, which already span areas like Construction & Energy, Global Property, and Professional Lines. The addition of Apollo’s broad product suite—covering Property, Casualty, Marine, Energy & Transportation, and Reinsurance—creates a more robust and resilient underwriting portfolio.

The deal structure itself reflects a deep alignment of interests. The $555 million price tag was financed with $371 million in cash and $184 million in Skyward common equity. Notably, Apollo's strategic investors and employees rolled a significant portion of their holdings into Skyward stock, with 3,679,332 shares issued at a value of $50.00 per share. This move ensures that key Apollo talent is invested in the long-term success of the newly combined organization, while financial investors were fully cashed out.

Fusing Innovation and Underwriting Expertise

Beyond market access, the acquisition is a significant technology and innovation play. Apollo has built a reputation as a data-driven and forward-thinking platform. Its Syndicate 1971, known as 'Apollo ibott,' is a prime example, offering a unique platform liability product specifically designed for the burgeoning digital and sharing economies. This kind of forward-looking product development is precisely what Skyward aims to leverage across its entire operation.

Integrating Apollo's digital systems and data analytics capabilities is expected to accelerate underwriting workflows, sharpen risk assessments, and enhance product development. The capital-light, fee-based model that Apollo employs is also seen as a major benefit, projected to add earnings ballast and provide greater financial optionality for Skyward. This fusion of Skyward's established market presence with Apollo's agile, tech-forward approach positions the combined company to better address emerging risks and capitalize on pricing power in the competitive specialty sector.

Leadership continuity is a critical component of the integration plan. Apollo CEO David Ibeson and his senior management team will join Skyward Specialty and continue to lead the Apollo business. This decision is designed to ensure a seamless transition, retain invaluable institutional knowledge, and maintain the innovative culture that made Apollo an attractive acquisition target. While the holding company will adopt the new unified brand 'Skyward Group,' both the Skyward Specialty and Apollo names will be maintained as distinct, market-facing brands to preserve their established reputations and customer trust.

A Strong Financial Blueprint and Positive Market Reception

The financial implications of the deal are substantial and have been met with a positive reception from the market. The acquisition was executed at what is considered an attractive valuation of less than 9 times Apollo's estimated 2025 EBITDA. Skyward projects the deal will deliver double-digit adjusted operating earnings per share (EPS) accretion within the first full year and add over $1.5 billion in managed premium to its books.

Following the closing, Skyward issued ambitious financial guidance for 2026. The company anticipates gross written premiums to fall between $2.65 billion and $2.8 billion, with a combined ratio between 90.5% and 91.5%. Net income is forecasted to be between $207 million and $216 million. This confident outlook builds on Skyward's strong performance in 2025, where its third-quarter results already showed a 51.6% rise in gross written premiums and an improved combined ratio of 89.2%.

Investor and analyst sentiment has been overwhelmingly favorable. Skyward's stock (SKWD) saw a 5% appreciation following the initial announcement and the release of its 2026 guidance. As of today, the stock is trading at $51.11, and multiple financial analysis firms have issued 'Buy' or 'Overweight' ratings. The consensus one-year average price target sits at $64.83, implying a potential upside of over 25% for investors. This market reaction underscores the belief that Skyward's strategic acquisition of Apollo is a well-timed move that aligns with broader M&A trends in the specialty insurance sector, where scale and technological prowess are becoming key differentiators.

The successful completion, which followed the receipt of all necessary regulatory approvals from bodies like the UK's Prudential Regulatory Authority (PRA) and Lloyd's of London in December 2025, places the new Skyward Group in a formidable position within the competitive global insurance landscape.