Senior Site Reliability Engineer at Calendly

Title: Senior Site Reliability Engineer

Location: Remote

What is Calendly?

Calendly takes the work out of scheduling so our customers have more time to work on what’s really important. Our software is used by millions of people worldwide with thousands more signing up every day. To maintain this exciting growth, we’re looking for top talent to join our team and help shape the future of our product.

Why join Calendly’s Engineering team?

At Calendly, the Senior Site Reliability Engineer is armed with a “measure everything mentality” and helps engineering teams improve the reliability, performance, resilience, and security of the services they own. Working with a well-defined continuous delivery process and a reasonably instrumented production environment, the successful candidate will be able to define SLOs and measure SLIs with an eye toward continuous improvement and an evolution at scale. The Senior SRE uses their expertise of the infrastructure to work together with and empower engineering teams. This includes enablement to fine-tune or achieve adequate monitoring, containerization of applications, CI/CD pipelines, orchestration, applying infrastructure changes utilizing IaC, and owning several processes pertaining to reliability. With a growing team and a mindset for scale, implement and operate Calendly’s next generation platform using cloud IaaS services. An ideal candidate demonstrates exceptional leadership in communicating patterns and improvements that automate tasks, improve stability, secure systems, and increase performance.

What are some of the high impact opportunities you’ll tackle?

  • Institute resilient infrastructure through source code based configuration (Infrastructure as code)
  • Demonstrate skills in evaluating, measuring, and improving rapidly evolving systems
  • Collaborate with engineering teams to understand and improve their systems
  • Organize a holistic ecosystem of infrastructure, tools, and capabilities that effectively provides visibility into the health of each component
  • Optimize CI/CD pipelines to provision, track, validate, sign, and securely deploy software
  • Grow expertise in cloud concepts, especially IaaS/PaaS with exposure to virtualization technology in support of building our enterprise container infrastructure
  • Implement high availability systems with automated failover across multiple availability zones
  • Lead postmortem of unexpected incidents to prevent future recurrence
  • Participate in an on-call rotation to support critical Calendly infrastructure
  • Foster environment of learning and knowledge dissemination
  • Define standard practices and tooling around new services, changes, incidents, postmortems and work and capacity to work with engineering teams to adopt those practices

This opportunity is for you if you have/are:

  • Engineering experience supporting high availability systems in production
  • Experience solving infrastructure problems with software
  • Strong technical knowledge of cloud infrastructure, distributed systems, and reliability practices
  • Experience with GCP and/or AWS
  • Software development experience (Ruby, Node, and Typescript experience a plus)
  • Experience deploying containerized services (Docker experience preferred)
  • Experience running and securing Kubernetes in production environments
  • Understanding of CI/CD pipelines and application delivery via GitOps
  • Varied experience in software monitoring tools
  • Understanding of security and the shared responsibility model
  • Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

If you are an individual with a disability and would like to request a reasonable accommodation as part of the application or recruiting process, please contact us at

Calendly is registered as an employer in many, but not all, states. If you are not located in or able to work from a state where Calendly is registered, you will not be eligible for employment.