Cowbell Cyber Raises $100M To Drive SME Insurance Adoption

‘Lots of MSPs have seen their customers get hit, and they’ve seen what happens when they don’t have cyber insurance. So that brought it to the forefront of their mind,’ says Cowbell Cyber COO Trent Cooksley.


Cowbell Cyber closed a Series B funding round to strengthen its data science capabilities and risk engineering functions and bolster its business with MSPs.

The Pleasanton, Calif.-based company plans to use the $100 million to obtain visibility into the entire small and medium-sized enterprise (SME) ecosystem and help policyholders understand where risk lies within their security stack, according to co-founder and Chief Operating Officer Trent Cooksley. The funding round was led by Anthemis Group and comes three years after Cowbell Cyber was founded.

“We have proven market fit and we’re started to hit that scaling phase where we really wanted to bolster what we’re providing to the market,” Cooksley told CRN. “It was a good time in terms of where our business was.”

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Cowbell Cyber has 23 million businesses with revenue of less than $250 million in its risk pool today and wants to get all 32 million SMEs into its ecosystem to further normalize and enrich its data, Cooksley said. The company uses this data to assess the vulnerabilities that policyholders have as well as the likelihood that the policyholder would experience a financial loss due to that specific vulnerability.

Meanwhile, demand from policyholders for a CISO-type deep analysis of their security risks has grown significantly, and Cooksley said Cowbell Cyber plans to expand its risk engineering team to satisfy that demand. The risk engineering team helps organizations control risks and can potentially provide recommendations and insights through the Cowbell Cyber platform, according to Cooksley.

Cowbell Cyber’s assessment is more insurance-focused than the vulnerability assessments offered by other cybersecurity vendors and is looking to determine how much policyholders need to have covered, how much they’re paying for their current security protection, and where exposure lies relative to risk.

From a go-to-market perspective, Cooksley said Cowbell Cyber is working with hundreds of MSPs to help them understand what their supply chain exposure looks like and what gaps the insurance provider can help them close. MSPs are often looking to partner with Cowbell Cyber to sell insurance to their customers, but sometimes want to use Cowbell to insure their own environments, Cooksley said.

MSPs are often unable to resolve ransomware attacks or pay the ransom on behalf of an individual customer, and Cooksley said channel partners without access to insurance coverage find that few services are available to them. Cooksley said MSPs often need help determining where the opening was that adversaries exploited, who came through the opening, and who was responsible for securing it.

“Lots of MSPs have seen their customers get hit, and they’ve seen what happens when they don’t have cyber insurance,” Cooksley said. “So that brought it to the forefront of their mind.”

Cooksley said MSPs are leveraging the Cowbell platform and using that to evaluate insurance exposure for their customers. Having a really robust risk pool is essential for the company’s ability to continuously assess the overall threat landscape and provide a tailored insurance product back to the policyholder, according to Cooksley.

“We have a lot of technology capabilities to deliver product within non-insurance ecosystems where it makes sense with digital distribution, instant quoting, and precise underwriting through our AI,” Cooksley said. “So there‘s a lot of value proposition.”