Participated · Series C · Dec 2024

Players Health offers a data-driven, tech-enabled platform delivering risk management services, reporting tools, and insurance products to youth, recreational, collegiate, and professional sports organizations. Founded by a former professional football player, the company focuses on athlete safety and compliance across the sports ecosystem. It has reached more than 5.5 million youth athletes and counts customers such as USA Softball, American Youth Soccer Organization, and Orangetheory. Players Health will use new funding to advance AI-powered product personalization, pursue strategic M&A to broaden capabilities, and expand its workforce. The company emphasizes standardizing best practices for athlete safety and aims to expand its nationwide reach. Player's Health (Ao1 Holdings Inc.) offers turnkey insurance and risk-management solutions for organized athletics, operating as a managing general underwriter. The company uses proprietary risk-management software and partnerships with sports-management platforms to track protocol evidence and deliver injury-management insights. Its platform provides levels of injury-management and protocol-tracking data previously unavailable in amateur sports. Leadership says the business exists to create safer environments for athletes and to give sports organizations the protection and tools they need. The company aims to grow its business with support from strategic investors. No revenue or user metrics were disclosed in the articles.

Participated · Series A · Jan 2023

Joyn Insurance is an insurance technology company led by CEO Seraina Macia that underwrites commercial insurance in the small and middle markets. The company offers E&S coverage for property, general liability and excess across more than 700 NAICS codes in 36 states and Washington, D.C. Joyn has bound more than 500 policies with approximately 80 trading partners, covering more than 300 insureds. Launched in July 2021 and based in New York, Joyn uses a technology-driven platform to deliver its insurance products. The company plans to use new funding to enhance its technology platform and data capabilities and to demonstrate the value of its offerings. It also intends to expand the size of its team by the end of the year. Joyn Insurance is a New York–based insurtech enterprise and newly formed Delaware-domiciled, licensed producer and general agent led by founder and CEO Seraina Macia. The company will underwrite commercial insurance for small and middle-market businesses, initially operating as a Managing General Agency. Joyn plans to deliver a digital commercial insurance experience and underwrite Excess and Surplus (E&S) products across six industry verticals. It aims to address underserved needs within the roughly $100B U.S. SME market. Joyn will leverage digital technology, data analytics, and automation as core elements of its product and distribution strategy. SiriusPoint will act as a strategic partner and capacity provider to support underwriting and growth.

Participated · Seed · Oct 2022

LuckyTruck is a modern insurance platform for commercial trucking that leverages data and automation to reduce friction across the customer journey. The company operates as a retail platform focused solely on trucking insurance and is headquartered in Cincinnati, OH. Led by new CEO Julie Zimmer, LuckyTruck intends to use recent funding to accelerate growth, expand operations and broaden its business reach. The team scaled rapidly in 2022, growing from 25 employees in January to more than 60 by October. Over its roughly four years of operation, the company has grown to more than 700 active customers. The platform emphasizes automation and data-driven processes to serve commercial trucking customers more efficiently.

Participated · Series A · Sep 2022

PolicyMe is a Canada‑focused digital insurance company whose product suite includes Life Insurance, Critical Illness Insurance, and newly launched Health & Dental coverage, alongside an end‑to‑end white‑labeled platform for partners. The company expanded from life insurance into Health & Dental and converted its digital customer journey into a comprehensive white‑label solution that integrates quoting, underwriting, and policy issuance. That platform is designed to cut partners' time‑to‑market to 3–6 months and already powers launches for Blue Cross Life and Securian Canada. Since its 2022 Series A, PolicyMe has scaled nationwide, selling over $10 billion in coverage, growing annual premium sales 5.5x, servicing thousands of Canadians monthly, and operating in every province. Headcount has nearly tripled to about 100 employees to support product and customer growth. PolicyMe has raised additional capital (CAD $30M) through equity and debt tranches to fund product expansion and B2B2C growth. The company is investing in data, analytics, and AI infrastructure to improve underwriting and streamline the customer journey, positioning itself to lead AI‑driven transformation in the insurance industry. PolicyMe is a digital-first Canadian life insurance provider that offers fully underwritten term life insurance through an online application. The company began with a coverage calculator and price-comparison platform and launched a fully underwritten digital product in March of last year with Canadian Premier Life Insurance Company. By automating underwriting and distribution, PolicyMe prices its product 10–20% lower than many traditional offerings; 84% of customers purchased without a medical exam and most can apply and secure a policy in 20 minutes or less. The company has sold over $5 billion in life insurance coverage and grew over 1,050% from 2019 to 2021. PolicyMe plans to scale a comprehensive product suite distributed direct-to-consumer and via B2B2C channels, launch an embedded solution with two fintech partners later this year, and release a critical-illness product covering over 40 conditions. Since March 2020 the team has more than tripled to 47 employees and is fully remote with optional office access in downtown Toronto. PolicyMe operates a digital life-insurance comparison site and buying flow. The company was founded in 2018 and is led by Andrew Ostro and Laura McKay, with a team of about 11 people. PolicyMe says it is trusted by over 30,000 Canadians and reports advising roughly 26% of those users not to purchase a PolicyMe product. SimilarWeb data cited in the articles indicates the site has relatively low web traffic. PolicyMe raised $3.3 million and will use the funds to enhance its life-insurance buying process with new technology and financial literacy tools. The company emphasizes transparent, personalized advice as a core part of its customer experience.

Participated · Seed · Sep 2022

Boundless Rider Insurance Agency is a Boston-based insurance claims company focused on riders of specialty vehicles. Led by CEO Blair Baldwin, the company aims to bring product innovation in claims and will offer coverage directly to consumers and through partners on a state-by-state basis beginning in late 2022. Eligible vehicles include motorcycles, recreational ATVs and UTVs, snowmobiles, scooters and mopeds, dirt bikes, and e-bikes; policies will be purchasable online or by phone. The company raised $4.75m in a Seed round led by American Family Ventures, with participation from The Cross Country Group, SiriusPoint, and Belmont Capital. Boundless Rider had previously raised a $2m pre-seed in March 2021, bringing total financing to $6.75m. The new capital will be used for investments in data science, partner integrations, and state expansion.