Skyward Group
Skyward Group is a public holding company based in Houston, Texas, representing the U.S. operations of Skyward Specialty Insurance Group and its Lloyd’s of London business, Apollo. The company specializes in providing specialty property and casualty insurance solutions tailored for global specialty markets. Skyward Group offers a wide range of commercial insurance products through its brands, including Accident & Health, Captives, Global Property, Industry Solutions, Professional Lines, Programs, Surety, and Transactional E&S. Its portfolio encompasses admitted and excess and surplus business
Investing activity
Skyward Group appears in 1 AI deal tracked by the Lounge deals desk, rounds totalling $27M, and led 1 of them. The rounds are mostly Seed, with a median round size of $27M. The most recent is Slingshot Insurance (Seed, $27M, Oct 2026).
Skyward Group most often invests alongside Rally Ventures and Jim Hays, and the companies it backs on Lounge are mostly in AI-native embedded insurance.
Deals
Frequently asked questions about Skyward Group
What AI companies has Skyward Group invested in?
Skyward Group's AI investments include Slingshot Insurance. The 1 round on Lounge are listed on this page with amounts, dates and co-investors.
Where is Skyward Group based?
Skyward Group is based in Houston, Texas, United States.
What stage does Skyward Group invest at?
In the rounds tracked on Lounge, Skyward Group has invested at Seed, with a median round of $27M. Skyward Group led 1 of those rounds.
Who does Skyward Group co-invest with?
Skyward Group's most frequent co-investors on Lounge are Rally Ventures (1 deal) and Jim Hays (1 deal).
How can founders reach Skyward Group?
Founders on Lounge can see Skyward Group's contact details in AI Investor Contacts (paid plans), check for a warm introduction through members who worked with the firm under Warm Paths, and add Skyward Group to their Investor Pipeline to track the conversation.