At-Bay and Cowbell both decided that a cyber policy should do more than pay a claim, but they built for different buyers. At-Bay wraps managed security services around the coverage; Cowbell tunes the underwriting itself to each small business's risk. Here's how they actually compare.
This is an independent comparison from QuoteSweep, which maps the modern commercial insurance landscape. QuoteSweep does not compete with any of these companies.
TL;DR: Both are cyber-focused MGAs that sell through intermediaries. At-Bay calls its model InsurSec — insurance bundled with managed detection & response and other security services in tiered packages — written on A++ rated capacity tied to Munich Re and distributed through brokers. Cowbell is purpose-built for small and mid-sized businesses, using its Cowbell Factors risk model for adaptive, continuous underwriting sold through agents and a direct console, with strategic Zurich backing. Choose At-Bay for security operations built into the policy; choose Cowbell for cyber coverage priced to a smaller business.
The one-line difference
- At-Bay calls its model InsurSec — insurance plus security — and packages managed detection & response, vulnerability scanning, dark-web monitoring, email-fraud alerts, and vCISO advisory into three coverage tiers for tech and mid-market companies.
- Cowbell is an adaptive cyber MGA purpose-built for small and mid-sized businesses, quantifying each account's risk with its Cowbell Factors model and adjusting coverage as that risk changes.
Model and coverage
Both go beyond a one-time transaction, but in different ways.
- At-Bay: security services are bundled into the policy across tiers — Core (vulnerability monitoring, vCISO advisory, email-fraud security, awareness training), Advanced (adds MDR for endpoints with 24/7 monitoring), and Complete (adds MDR for email with next-gen security). Policyholders manage it all through one dashboard.
- Cowbell: the model is adaptive and continuous rather than security-services-based. Its Cowbell Factors™ quantify an account's risk exposure, benchmark it against millions of accounts, and highlight vulnerabilities, feeding a closed-loop approach — assess, insure, respond, and improve.
The practical distinction: At-Bay's differentiator is the managed security stack it attaches to the policy; Cowbell's is the risk model that prices and re-prices the policy to the account.
On lines, both write cyber plus a technology-professional line, but the third line differs — At-Bay adds miscellaneous professional liability, while Cowbell adds management liability for SMB leaders.
Coverage and capacity at a glance
| At-Bay | Cowbell | |
|---|---|---|
| Model | InsurSec (insurance + bundled security) | Adaptive, continuous underwriting (Cowbell Factors) |
| Cyber | ✓ | ✓ |
| Technology / professional E&O | ✓ (Technology E&O) | ✓ (Professional Indemnity) |
| Miscellaneous Professional Liability | ✓ | — |
| Management Liability | — | ✓ |
| Bundled MDR / security services | ✓ (tiered) | — (risk tooling, not MDR) |
| Distribution | Brokers (At-Bay Broker Platform) | Agents + direct console |
| Capacity / backing | A++ rated, tied to Munich Re's HSB | Strategic Zurich backing; partners not detailed on site |
| Reach | Licensed in all 50 states (surplus lines) | US, UK, Australia |
At-Bay's lineup leans toward technology firms (cyber, technology E&O, MPL) with security operations attached; Cowbell's leans toward SMB leaders (cyber, professional indemnity, management liability) with risk tooling attached.
Funding and scale
- At-Bay: per third-party reporting, a $185M Series D at a $1.35B valuation in 2021 (co-led by Icon Ventures and Lightspeed); roughly $296M total. It says it protects 40,000+ policyholders. Founded 2016, San Francisco.
- Cowbell: per third-party reporting, a $60M Series C led strategically by Zurich Insurance Group in 2024; ~$202M raised total. Founded 2019, Pleasanton, CA.
Both valuations and figures come from earlier rounds and company-reported sources that are not independently audited — read them as scale signals, not current prices.
Who each one fits
- Choose At-Bay if you're a tech or mid-market company that wants real security operations — managed detection & response, vulnerability and dark-web monitoring, vCISO advisory — built into the cyber policy, and you want to pick your security tier explicitly. You'll buy through a broker.
- Choose Cowbell if you're a small or mid-sized business that wants cyber coverage priced to your size, with tooling to understand and reduce your risk that adjusts as your risk changes. You can buy through an agent or Cowbell's direct console.
For most buyers the deciding factors are how much managed security you want bundled in (At-Bay's strength), how small the business is (Cowbell's focus), and which third line you need — miscellaneous professional liability from At-Bay or management liability from Cowbell.
Frequently Asked Questions
Are At-Bay and Cowbell carriers or MGAs?
Both are cyber-focused managing general agents/underwriters that write on capacity partners rather than carrying the risk on their own balance sheet. At-Bay is an insurance agency and surplus-lines broker licensed in all 50 states, writing on A++ rated capacity tied to Munich Re's HSB. Cowbell is a cyber-focused MGA; per reporting, Zurich Insurance Group is a strategic backer.
What's the core difference between them?
Emphasis and buyer. At-Bay's InsurSec bundles managed detection & response and other security services into tiered cyber policies for tech and mid-market firms. Cowbell is purpose-built for small and mid-sized businesses, using its Cowbell Factors model for adaptive, continuous underwriting that adjusts as risk changes.
Which is cheaper?
Neither publishes flat pricing. At-Bay's premium depends on the business, its security posture, and the coverage; Cowbell's premium is priced to the account's Cowbell Factors and coverage. Compare quotes for the same limits.
Where can I compare more cyber insurers?
See the cyber insurtech hub for side-by-side ratings and facts across the category, including both of these companies.
Get a quote
The bottom line
At-Bay and Cowbell agree that cyber insurance should help manage risk, not just pay for a breach — and they execute differently. At-Bay is the security-services specialist, bundling managed detection & response into tiered policies for tech and mid-market firms on Munich Re-backed paper. Cowbell is the SMB specialist, pricing adaptively through its Cowbell Factors model with strategic Zurich backing. Match the choice to your size, the lines you need, and how much managed security you want in the policy — an agent or broker can quote both.
Compare both, plus the rest of the field, on the cyber insurtech hub, or read the full At-Bay and Cowbell profiles.
