WithCoverage Raises $42 Million to Rebuild Insurance for High-Growth Businesses

Insurance has long been treated as a necessary but frustrating cost for growing businesses, often purchased once a year and rarely revisited until something goes wrong. For ambitious companies scaling rapidly, this approach has created a dangerous gap between real operational risk and outdated insurance coverage. New York based InsurTech startup WithCoverage is positioning itself as a direct response to this problem. The company has raised $42 million in a Series B funding round led by Sequoia Capital and Khosla Ventures, with participation from 8VC and Crystal Venture Partners. The funding highlights increasing investor interest in rethinking insurance brokerage as a continuous, technology driven function rather than a transactional service. WithCoverage argues that most modern businesses lack in house risk management teams, leaving them overinsured in some areas, underinsured in others, and largely in the dark about their actual exposure.

Founded with the goal of creating a new standard for business insurance, WithCoverage describes itself as a modern risk management solution rather than a traditional broker. The company combines an expert insurance team with a technology platform designed to give businesses visibility and control over their risk profiles as they grow. Instead of fragmented policies and opaque paperwork, WithCoverage offers a centralized system that organizes coverage, tracks changes in business operations, and adapts insurance needs accordingly. This approach reflects a broader shift in enterprise tooling, where software is increasingly expected to evolve alongside a company rather than remain static. WithCoverage positions insurance as an operational layer, similar to finance or compliance, rather than a once a year procurement task handled in isolation.

The company’s client list offers insight into the type of businesses driving demand for this shift. Brands such as GoPuff, Bombas, Eight Sleep, Salt and Straw, and Blank Street operate in fast moving consumer, logistics, and retail environments where risk profiles change quickly. Traditional insurance models often fail to keep pace with such growth, leading to coverage gaps that only become apparent after costly incidents. WithCoverage’s platform is built to address this by aligning insurance coverage with real time business evolution. The company emphasizes transparency and organization as core features, aiming to replace the confusion that often surrounds insurance documentation with clarity and accountability.

Why Sequoia and Khosla Are Betting on WithCoverage ?

The Series B round led by Sequoia Capital and Khosla Ventures is particularly notable given the history of both firms of backing companies that redefine entire categories. Their involvement suggests confidence in the broader thesis that insurance brokerage  is overdue for structural change. Over the past decade, many InsurTech startups focused on digitizing policy purchases or offering niche insurance products. WithCoverage’s approach is different in that it targets the brokerage layer itself, which remains heavily relationship driven and manual. By introducing software into this layer, the company is attempting to transform how businesses interact with insurers, brokers, and their own risk data.

Beyond funding headlines, the rise of WithCoverage reflects a deeper trend in how businesses think about risk. As companies become more data driven and operationally complex, risk management is no longer limited to catastrophic events. Cybersecurity, supply chain disruptions, regulatory exposure, and operational liabilities are now central concerns for leadership teams. Insurance is increasingly expected to function as a strategic safeguard rather than a compliance checkbox. The model of WithCoverage aligns with this reality by treating risk management as an ongoing process supported by both human expertise and technology. This hybrid approach acknowledges that while automation is powerful, insurance decisions still require judgment and industry knowledge.

Looking ahead, the new capital is expected to support further development of the platform of WithCoverage, expansion of its expert team, and deeper integration of analytics into its risk assessment processes. The company operates in a highly competitive environment that includes legacy brokers experimenting with digital tools and newer InsurTech firms attempting to carve out specialized niches. Whether WithCoverage can scale its model without losing the service quality that differentiates it will be a key question. Still, the funding round signals growing belief that the future of insurance brokerage will be defined by platforms that offer clarity, adaptability, and continuous engagement rather than static policies and annual renewals.

The momentum of WithCoverage reflects a broader realization that insurance can no longer remain static in a world of rapidly evolving businesses. By treating risk management as a continuous, technology supported function, the company is addressing a structural weakness in traditional brokerage models. The real test will be whether such platforms can maintain trust and expertise while scaling through software. If successful, this approach could redefine how modern companies think about insurance altogether.