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How Zywave scales consistently and securely with Octopus


“Each product we bring on is different, and every team has a different process. The fact that we can store all the steps and patterns improves efficiency. It means we aren’t having to reinvent everything every time.”

- John Cruikshank, Vice President, Engineering

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Their story

Zywave is a leading insurance technology company with a portfolio of cloud-based sales management, client delivery, content, and analytics solutions. The company offers an all-in-one platform with data and a comprehensive content library so insurance agencies can make smarter business decisions throughout the customer lifecycle.

More than 5000 insurance agencies use Zywave’s software, including 95 of the top 100 US insurance firms. Zywave started in the benefits space and has since expanded its tooling across the other pillars of insurance.

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Zywave has used Octopus Deploy for over 10 years. The team initially implemented Octopus because their deployments were largely .NET/IIS deployments, and the Tentacle architecture gave them the granular control they needed.

Over time, Zywave has expanded its software offering and made several acquisitions. With new software teams with their own deployment processes and tooling, Zywave’s requirements expanded beyond a single space.

Zywave began to modernize from IIS to Kubernetes a few years ago. More recently they have been looking into everything-as-code as a way to scale further to meet the demands of over double the number of teams and a wide range of deployment stacks.

Zywave hoped to bring its teams together with a consistent, easy-to-implement deployment process with access control and auditability across environments.


In 2022, Zywave re-evaluated its CI/CD pipeline to ensure it could expand with them. Previously running on one server, the team saw the need to scale their capacity. Zywave found Octopus still met its needs for auditability and security and the team could use Octopus’s new features to help them scale.

As they expand, Zywave are using Octopus projects to give them flexibility with distinction. Octopus lets them isolate their technology stacks across their product offerings and acquisitions. Zywave then manages access to each stack to meet security and auditing requirements. This allows them to scale their deployments as their business acquires new products.

Using step templates also means new products and teams can set up their deployments quickly using repeatable processes. This creates consistency, even when some teams are trying deployment automation for the first time.

To help shape an everything-as-code approach, Zywave also takes advantage of Octopus Deploy’s Config as Code solution. For everything outside of Octopus projects, Zywave uses Terraform to configure projects. With up to 95% of their activities in Octopus happening in projects, they use Terraform to control the less-frequent tasks.


Octopus has improved software delivery and supported Zywave’s growth in many ways:

Consistency and reliability while scaling: By reshaping its use of Octopus Deploy as the company scales, Zywave has ensured repeatability and reliability across its deployments. As the company acquires products and teams at different points in their modernization journey with varying levels of automation experience, Octopus creates consistency for Zywave.

Easy onboarding to support growth: Step templates also make it quick and easy to onboard new teams and automate their deployments without re-learning code

Secure, auditable, compliant processes: By using Octopus, Zywave meets its compliance and auditing objectives. Projects in Octopus let Zywave control access to deployments to maintain security and provide visibility for auditing purposes.

Modernizing workflows with everything-as-code: Using Config as Code in Octopus has also helped Zywave move towards an everything-as-code approach without compromising on deployments. Zywave still benefits from the usability of the Octopus UI throughout its CI/CD workflow.

Shout out to @OctopusDeploy for making their software so easy to work with. Just upgraded a 2 year out of date instance and migrated it to a new server and it worked with no effort beyond what their documentation said to do.

Twitter user Alex Dent Alex Dent

We've been overhauling our internal infrastructure and back-end systems over the past month, including a move back to full @OctopusDeploy deployments; rediscovering how nice it is to have a platform-agnostic orchestrator that can deploy practically anything, anywhere ❤

Twitter user Nicholas Blumhardt Nicholas Blumhardt

Tools like @OctopusDeploy can be great in enabling culture change, we've been able to scale and improve our configuration story since we started using it.

Twitter user Niel Chalk Niel Chalk