Slingshot Insurance emerges from stealth with $27 million seed investment to build ai-native infrastructure for embedded insurance. Oct 22, 2026, 09:00 ET Rally Ventures and Skyward Group co-led the round with participation from additional P&C industry veterans to unlock the untapped, high-growth embedded market MINNEAPOLIS, Oct. 22, 2026 /PRNewswire/ - Slingshot Insurance, the AI-native insurance company built for the embedded economy, today emerged from stealth with $27 million in seed financing co-led by Rally Ventures and Skyward Group. Several P&C industry veterans also participated in the oversubscribed round, including Jim Hays, who will join the company's Board of Directors. Embedded insurance is emerging as one of the fastest-growing segments of the P&C market. Industry forecasts suggest it could grow from roughly 3% of global P&C premiums today to nearly 20% over the next decade, significantly outpacing the broader market. Slingshot, co-founded by Rally Ventures and Ethan Genteman, former Chief Actuarial Officer at Palomar Holdings, is purpose-built to help those serving the embedded insurance market, including industry vertical software platforms, managing general agents (MGAs), and insurance distributors, capitalize on that shift. The platform gives them the technology, capacity, and speed to launch and scale insurance products for niche and rapidly evolving embedded opportunities, such as amateur sports, travel, and the gig- and independent-work economy. "Traditional carrier infrastructure wasn't built for embedded insurance's risk and economic model. Embedded products tend to be higher-frequency, lower-severity risks, often with smaller premiums, while incumbent systems and operating models carry fixed costs designed for a much different market," said Ethan Genteman, co-founder and CEO of Slingshot. "Our infrastructure changes those economics by dramatically lowering the cost of administering policies and accessing capital. That makes products viable that historically were not, creating value for customers and capital providers while opening up entirely new embedded insurance opportunities." Slingshot has developed an AI-native infrastructure designed for the unique demands of the embedded insurance market. High-volume products create transaction and data complexity that traditional spreadsheets, email, and disconnected legacy systems were never designed to manage efficiently. Slingshot replaces that patchwork with a single integrated system that uses AI to automate complex workflows and APIs to connect seamlessly with MGAs, distribution platforms, and capital providers. The result is infrastructure designed to operate embedded products profitably and at scale. Every decision is auditable, reconcilable, and explainable, giving MGAs and capital providers greater transparency, speed, and insight. Rally Ventures co-founded Slingshot alongside Genteman, betting early on embedded insurance as a large and fast-emerging market. "The real growth opportunity in insurance today is in the small, everyday policy sold right at checkout," said Justin Kaufenberg, managing director at Rally Ventures. "We built Slingshot to provide MGAs and others serving the embedded market with the infrastructure to launch new products at a speed that simply has not been possible before." Vertical Insure, an embedded insurance MGA serving 750,000+ customers at a $25 average premium, signed on as an early customer and design partner because it needed faster, technology-enabled carrier support. "We can design the products our customers need almost overnight, but the industry is highly regulated, and we need delegated authority just to write and distribute what we've built. The antiquated approval process on the carrier-side slows everything down," said Brock Noland, co-founder and CEO of Vertical Insure. "Our business really comes down to technology and good data - traditionally, carriers haven't had either, and that's exactly what Slingshot brings to the table." Those serving the embedded insurance market can learn more about Slingshot at www.slingshotinsurance.com. About Slingshot Insurance Slingshot Insurance is an AI-native insurance company built for the embedded economy. For managing general agents (MGAs) and others looking to capitalize on the fast-growing embedded insurance market, Slingshot provides the infrastructure to replace the fragmented legacy tools and inefficient processes that have historically hindered innovation in higher-frequency, lower-severity insurance products. The AI-native platform automates complex, data-heavy workflows while ensuring every decision is fully auditable, reconcilable, and explainable, providing the transparency and speed required to operate embedded products profitably and at scale across emerging markets such as travel, amateur sports, and the gig economy. SOURCE Slingshot

Skyward Group (SKWD) stock: slightly drop as McHarg named successor as CFO plans exit. Skyward Group appoints Taryn McHarg as CFO successor ahead of Mark Haushill's 2027 retirement. Tldr. Table of Contents * Skyward Group names Taryn McHarg as CFO successor ahead of Haushill retirement. * SKWD shares fall 1.53% to $55.54 after a sharp early drop from above $57.50. * Mark Haushill will retire as Skyward Group CFO in March 2027 after over a decade. * McHarg brings senior finance experience from Apollo, BUPA and Ernst & Young. * Haushill will remain a Senior Advisor through 2027 to support the transition. Skyward Specialty Insurance Group (SKWD) fell 1.53% to $55.54 after dropping sharply during Thursday's morning trading. The shares later recovered part of the decline after trading above $57.50 earlier in the session. Meanwhile, Skyward Group announced a planned CFO transition that will extend through the end of 2027. Skyward Group names McHarg as next CFO. Skyward Group said Chief Financial Officer Mark Haushill plans to retire from his position on March 31, 2027. Taryn McHarg, currently Apollo CFO and Skyward Group Deputy CFO, will succeed Haushill after his retirement. Therefore, the company will promote an existing executive rather than recruit an external finance chief. McHarg has served as Apollo's CFO for more than four years and brings extensive insurance sector experience. Before Apollo, she spent nine years at BUPA and eventually became CFO of its international markets business. Earlier, she spent seven years at Ernst & Young, strengthening her accounting and financial management background. The appointment follows Skyward Group's January 2026 acquisition of Apollo Group Holdings, which expanded the company's specialty insurance operations. McHarg already holds senior finance responsibilities across the combined organization through her Deputy CFO position. As a result, Skyward expects the internal appointment to support continuity across financial planning and corporate operations. Haushill plans retirement after decade at Skyward. Haushill will retire after more than ten years with Skyward and several major changes across the company. During his tenure, Skyward completed its 2023 initial public offering and strengthened its broader capital position. He also held a central finance role during the company's expansion and Apollo acquisition. Skyward also improved its financial strength during the period, including progress in its AM Best financial rating. Those developments accompanied the company's shift toward a larger and more diversified specialty insurance business. Haushill therefore leaves after overseeing several important financing, reporting, and corporate development milestones. However, Haushill will remain involved after leaving the CFO position to support the leadership transition. He will serve as a Senior Advisor through the end of 2027 under the company's succession plan. That arrangement gives McHarg continued access to institutional knowledge during her first months leading Skyward's finance organization. Skyward builds on Apollo integration. Skyward Group now combines Skyward Specialty and Apollo under a broader specialty insurance organization with several operating businesses. The Apollo acquisition expanded the group's market reach and increased the importance of coordinated financial leadership. The CFO succession arrives during an important stage of the company's integration strategy. McHarg will inherit responsibility for financial planning as Skyward develops opportunities across the combined insurance platform. Her existing roles provide direct experience with Apollo's finances and Skyward Group's wider financial priorities. This background could simplify the transfer of responsibilities when Haushill formally leaves the CFO position. Skyward described the succession structure as part of its long-term approach to executive development and corporate stability. The company has more than seven months before McHarg takes the CFO role in March 2027. Until then, Haushill and McHarg will continue working through the transition while Skyward advances its post-acquisition strategy. Limited Time Offer Get 3 free stock ebooks. Discover top-performing stocks in AI, Crypto, and Technology with expert analysis. * Top 10 AI Stocks - Leading AI companies * Top 10 Crypto Stocks - Blockchain leaders * Top 10 Tech Stocks - Tech giants