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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. 


Skills we need:
  • 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).



Skills we’d like:
  • 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 uscareers@simplybusiness.com.


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/ 

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CEO of Simply Business
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What You Should Know About Senior DevOps Engineer, Simply Business

Looking for an exciting opportunity to elevate your career? Simply Business is searching for a Senior DevOps Engineer in Boston, MA, who is ready to take our DevOps culture to the next level. If you're the type of person who enjoys creating solutions and automating processes, we want you on our team! At Simply Business, we're not just about insuring small businesses; we’re about empowering them through innovative technology and a seamless insurance-buying experience. In this role, you will be hands-on in building scalable, secure, and reproducible environments tailored to our Platform as a Service (PaaS). Your expertise in cloud hosting, particularly with AWS, Azure, and GCP, will be vital as you develop and optimize our deployment pipelines. We embrace a ‘you build it, you run it’ philosophy, so you’ll be encouraged to think critically about how to automate systems and solve problems before they arise. By joining our diverse and inclusive culture, you’ll be part of a talented team that values continuous learning and collaboration. You'll not only support our robust infrastructure but also contribute to designing systems that inspire and enable exceptional user experiences. Plus, with our amazing benefits, professional development opportunities, and a hybrid work schedule, Simply Business is more than just a job—it’s a place where you can truly thrive and make an impact. Ready to make your mark? Apply today!

Frequently Asked Questions (FAQs) for Senior DevOps Engineer Role at Simply Business
What are the responsibilities of a Senior DevOps Engineer at Simply Business?

As a Senior DevOps Engineer at Simply Business, you will focus on automating processes, building scalable infrastructures, and supporting our Platform as a Service (PaaS). Your primary responsibilities include creating production-ready solutions, implementing Infrastructure as Code practices, and ensuring our systems remain secure and auditable. You'll also embrace chaos engineering principles, contributing to our DevOps culture by optimizing deployment pipelines and fostering a self-service environment for our engineering teams.

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What qualifications do I need to become a Senior DevOps Engineer at Simply Business?

To qualify for the Senior DevOps Engineer position at Simply Business, candidates should have strong Linux systems administration skills and hands-on experience with cloud platforms such as AWS, Azure, or Google Cloud. Familiarity with continuous delivery and automation tools like Ansible, Terraform, and Docker is essential. Additionally, candidates should possess excellent programming skills in any language and a solid understanding of infrastructure as code concepts to thrive in this dynamic role.

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What technologies does Simply Business use for DevOps?

At Simply Business, our DevOps technology stack includes AWS for infrastructure, along with tools like GitHub Actions, Codebuild, Terraform, and Ansible to streamline deployment processes. We leverage Docker for containerization and employ monitoring and logging tools like New Relic and ELK. Our focus on creating a self-service, automated environment allows engineering teams to manage their own applications efficiently while adhering to best practices in security and performance.

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Can you describe the team culture for Senior DevOps Engineers at Simply Business?

The team culture for Senior DevOps Engineers at Simply Business emphasizes collaboration, continuous improvement, and a commitment to innovation. We promote a friendly, inclusive atmosphere that fosters professional growth and encourages team members to challenge conventions. Our approach of being product-driven rather than project-driven ensures that each engineer has the opportunity to make meaningful contributions while enjoying a healthier work-life balance through our hybrid working model.

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What benefits can I expect as a Senior DevOps Engineer at Simply Business?

As a Senior DevOps Engineer at Simply Business, you'll enjoy a competitive benefits package that includes comprehensive medical, dental, vision, and prescription coverage, participation in the company's bonus program, and a 401(k) plan with a generous employer match. Additionally, we offer 25 days of vacation, excellent learning and development opportunities, team outings, and a flexible hybrid work model to fit your lifestyle, all contributing to a fulfilling work experience.

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Common Interview Questions for Senior DevOps Engineer
How do you manage infrastructure as code in your previous roles?

In my previous roles, I managed infrastructure as code by using tools like Terraform and Ansible to automate deployment processes. This approach allowed me to create version-controlled templates for all my infrastructure components, enabling reproducibility and reducing configuration drift. I also integrated these practices into CI/CD pipelines for continuous deployment to ensure a stable and secure environment.

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Can you explain a challenging project you worked on as a DevOps Engineer?

One challenging project involved migrating our infrastructure to a new cloud provider while ensuring minimal downtime. I developed a detailed plan that included replicating existing configurations, testing deployment scripts in staging environments, and executing a blue-green deployment strategy. Regular communication with team members helped us coordinate effectively, and the migration was successful with zero downtime, showcasing our capability to handle critical changes.

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What is your experience with monitoring and logging tools?

I have extensive experience using monitoring tools like New Relic and ELK Stack for logging and visualization. In my previous roles, I have set up alerts based on performance metrics and logs to proactively address any issues. By implementing dashboards, I provided real-time visibility for the engineering teams, enabling us to troubleshoot quickly and maintain system health effectively.

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How do you approach security in a DevOps environment?

In a DevOps environment, security is paramount. I adopt a 'security by design' philosophy, ensuring that security practices are integrated from the initial development stages. This involves automating security checks in CI/CD pipelines, using tools for secrets management, and regularly auditing configurations against best practices. I also promote a culture of security awareness among team members to ensure everyone understands their role in safeguarding our applications.

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Describe your experience with continuous delivery and deployment.

I have successfully implemented continuous delivery and deployment (CD/CD) pipelines using tools like Jenkins and GitHub Actions. This involved automating testing, building, and deployment processes, which allowed us to consistently deliver updates to production with high confidence. An essential part of my role was to define clear workflows and best practices, ensuring all team members could contribute to and understand the process.

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What strategies do you use for troubleshooting in a production environment?

When troubleshooting in a production environment, I first gather logs and metrics to identify the issue's root cause. I value the use of monitoring tools and set up alerts to notify me of any anomalies. Once the issue is pinpointed, I apply a systematic approach to implement a fix, document the process, and ensure preventative measures are in place to avoid recurrence. Collaboration with team resources is also crucial for effective resolution.

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How familiar are you with container technologies?

I have hands-on experience with container technologies, primarily Docker. I've utilized Docker to package applications and their dependencies in a consistent environment, which significantly accelerates deployment processes. I also have experience with orchestration tools like Kubernetes, focusing on managing containerized applications at scale, ensuring high availability, and simplifying system management.

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What tools do you prefer for infrastructure automation, and why?

My preferred tools for infrastructure automation include Terraform for its declarative infrastructure model and Ansible for its simplicity in configuration management. Terraform's ability to manage infrastructure across multiple cloud providers is a significant advantage, while Ansible's agentless architecture makes it easy to implement in diverse environments. Both tools empower teams to deploy consistent and reproducible infrastructure quickly.

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How do you ensure continuous improvement in your DevOps practices?

Continuous improvement in DevOps practices is achieved through regular retrospectives and feedback loops. I encourage open discussions on what went well and what can be improved. By tracking key performance metrics, we can identify areas for optimization and implement changes iteratively. Additionally, staying up-to-date with industry trends and integrating new tools and technologies helps us evolve our practices constantly.

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What do you consider the most critical skills for a Senior DevOps Engineer?

The most critical skills for a Senior DevOps Engineer include strong technical knowledge in cloud platforms, solid scripting or programming abilities, and effective automation expertise. Additionally, excellent problem-solving skills and a proactive approach to system monitoring and troubleshooting are crucial. Strong collaboration skills are also important since DevOps professionals work closely with development and operations teams to drive efficiency.

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If you’re smart, passionate about delivering brilliant customer experiences across an integrated online and offline user journey, and enjoy solving complex challenges then you should apply to join our team.

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Full-time, hybrid
DATE POSTED
March 18, 2025

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