Senior DevOps Engineer

Simply Business is a digital insurance brokerage that specializes in one thing: protecting the businesses our customers are working hard to build. We’re doing this by simplifying the insurance-buying process for all small businesses, blending together a combination of technology, data, and insurance knowledge. Our proprietary technology platform allows small business owners to easily search and compare quotes from over 20 top-rated insurance providers, customize their coverage, and purchase and access their policies - all online.

Founded in the UK in 2005, Simply Business is an insurtech pioneer with nearly 20 years of experience supporting small businesses. Simply Business is passionate about building an outstanding product for our customers - one that empowers their entrepreneurial spirits.

More importantly, we’re doing it all while taking care of our people. We’ve consistently been named a best place to work, including most recently ranking in Built In’s 2025 Best Companies to Work for in the US (Top 100), and Best Places to Work in Boston.

We want team members who have the drive to challenge boundaries. If you’re smart and passionate about delivering brilliant customer experiences, we’d love to hear from you.

What you’ll be doing

You will help bring us closer to our DevOps nirvana and contribute to our Platform as a Service and DevOps culture (test driven infrastructure, automate everything, self-service tooling).

We are product driven, not project driven. Our PaaS, built on cloud infrastructure, is our product and the rest of the business our customers.

You will be hands-on in creating solutions to build and automate environments for production use. You understand the need to build scalable, secure, auditable, reproducible and usable infrastructure. You are security minded and endorse chaos engineering along with the approach of “you build it, you run it” and “you break it, you fix it”.

You will be required to be part of the on call rota, and believe that through well-designed systems and automation you will never be called.

We are mostly hosted in AWS (and annually attend re:Invent) and have built a PaaS on top to allow our product teams to deploy their applications using a Codebuild / GitHub Actions/Docker/Ansible/Terraform driven, region agnostic, blue-green automated deployment pipeline; this offers both AMIs and Docker images for deployment to our respective AWS EC2 and ECS production environment. We also use Azure and GCP with zero on-prem infrastructure.

In front of this we offer a self-service load balancing solution along with a DSL-based approach for creating and managing our subdomains with regards to DNS, SSL certificates, traffic manager routing and monitoring. This framework is all done as Infrastructure as Code including integrations of other AWS services (e.g. RDS, S3), with a focus on providing the guardrails for immutable systems and making it as self-service as possible for the Engineering Teams.

We work in a timely, prioritised and start small manner. We look at the highest pain points for both Dev and Ops and work backwards. We continuously re-evaluate using the right tool for the DevOps job and making abstraction easy.

• Linux systems administration.
• Experience of cloud hosting such as AWS, Azure or Google Cloud Platform.
• Experience with continuous delivery / provisioning / deployment.
• Building and managing production public-facing sites.
• Familiarity with the concept of ‘infrastructure as code’.
• Experience with automation tools such as Ansible, Terraform and CloudFormation (but not limited to those mentioned) 
• Strong programming skills (in any language).

• Experience with hosting internet applications - DNS, load balancing, internet protocols, SSL etc... 
• Experience of monitoring tools such as New Relic.
• Experience of logging tools such as ELK.
• Experience of secrets management.
• Experience of container technologies such as Docker.
• Networking skills.
• Experience of software / infrastructure testing and ideally TDD.

Here are some of the great benefits and perks that come from being a Simply Business employee:

-Group plan for medical, dental, vision, and prescription drug coverage

-Short term disability, long term disability, and life insurance coverage

-Participation in the Company’s bonus program-Participation in 401(k) plan with a 5% employer match

-Commuter benefits to help cut down on parking and public transit costs

-25 days of vacation time plus 10 sick days and 10 company holidays

-A genuine investment in your learning and development-Regular team outings and volunteer opportunities

-An awesome office space

-A hybrid working model, giving our employees great choice and flexibility to work in a way that’s best for their particular job, their teams, and their lives.

Simply Business is an equal opportunity employer. We’re committed to welcoming and helping employees grow within an inclusive & diverse culture. And that commitment starts with our interview process.

Once you apply, your info will be reviewed by a team with a mix of levels and experiences. We pride ourselves on fostering a sense of community, which is only made stronger by each individual at SB, so you’ll have the opportunity to meet a variety of people throughout the process. Get excited!

Most of our first round interviews will take place over Zoom. In subsequent interviews, there may be an opportunity/expectation to meet team members in person.

If it looks like you could be a good fit for the role, we’ll ask you to interview on Zoom first regardless – you’ll need WiFi and a laptop, or a 4G-enabled smartphone. If you don’t have access to either of these, or you need support with your application, get in touch with us at [email protected].

Please email us with any questions or if you want to pause your application for a bit – we’ll be happy to keep you updated on future opportunities like the one above. Want more info on working at Simply Business? Check out our careers page: simplybusiness.com/careers/