Cowbell is trying to do something most cyber-insurance startups never manage: grow bigger without getting sloppier.

The Silicon Valley–born insurer, which made its name selling adaptive cyber coverage to small and mid-market companies, says it is entering a new phase of its life—one defined less by land-grab expansion and more by disciplined scale. After pushing into Australia and steadily broadening its portfolio, Cowbell is repositioning itself as a wider digital protection platform, blending cyber insurance with professional and management liability, financial lines, and resiliency services.

For Cowbell, this is about maturing alongside the threat landscape it underwrites. Cyber risk has become inseparable from business risk, and insurers that once focused narrowly on ransomware payouts now find themselves pulled into governance failures, operational outages, and AI-driven incidents that blur traditional policy boundaries. Cowbell’s answer is a five-part growth strategy: expand internationally, deepen financial lines, build out resiliency services, push further into the mid-market, and turn its technology into subscription-based offerings for brokers and partners.

“As we enter this new cycle, parlaying our success in new products, new services, and new markets over the past 18 months, we are poised to scale responsibly and profitably,” said Jack Kudale, Founder and CEO of Cowbell. “Cowbell has built a solid foundation of technology, talent, and trust. Now, we’re focusing on translating that strength into sustained growth, global expansion, and operating profitability while continuing to deliver protection that creates confidence, not complexity.”

That emphasis on profitability matters. Cyber insurance has been notoriously volatile, with some carriers retreating after underestimating the cost of correlated losses and systemic events. Cowbell says its data-driven underwriting model—paired with continuous risk assessment—has helped it stay in the game while many competitors pulled back. The company now insures roughly 30,000 small and midsize enterprises worldwide, representing about $610 billion in insured revenue, and claims that a majority of its customers have stayed with the platform for more than three years.

To support this next chapter, Cowbell has brought in John Botros as chief financial officer. Botros arrives from Resilience, where he helped guide one of the sector’s most closely watched cyber-risk firms through rapid growth, investor scrutiny, and board-level strategy. At Cowbell, he will oversee global finance operations as the company balances expansion with tighter operational discipline.

The timing is deliberate. As cyber risk spreads across supply chains and regulatory regimes harden globally, insurers are under pressure to prove they understand the businesses they cover—not just the breaches they pay for. Cowbell says it has already paid out more than $275 million in claims and built a global risk pool spanning 55 million small and mid-sized organizations, data it believes can be leveraged far beyond traditional underwriting.

The bet is that cyber insurance’s future looks less like a reactive safety net and more like a continuously updated operating system for digital risk. If Cowbell can pull that off—scaling internationally while keeping losses predictable—it could offer a rare counter-narrative in an industry better known for boom-and-bust cycles than sustainable growth.