Role Description Ready to make a serious impact? Millions of people already rely on Calendly, and we’re still in the midst of exciting product growth — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey. We are looking for a Site Reliability Engineer who will bring creative problem solving and a keen eye for detail. You will report to a Senior Manager of Engineering and be responsible for designing, building, maintaining, and operating our next-generation infrastructure platform. With a growing team and a mindset for scalability, SREs build their own tools, deploy open-source solutions, and consume cloud services as needed to extend the platform. A day in the life of a Site Reliability Engineer at Calendly includes: - Building tools and applications to extend Calendly’s infrastructure platform - Evaluating and deploying cloud native open source tools - Exercising expertise in cloud infrastructure concepts and patterns - Instituting resilient infrastructure through Infrastructure as code - Maintaining and improving observability of our infrastructure platform - Participating in an on-call rotation to support the infrastructure platform - Fostering a collaborative environment of learning and knowledge dissemination - Defining standard practices and tooling around new services, changes, incidents, postmortems, and capacity management Qualifications - An eagerness and drive to learn, and the skills for sharing your knowledge with and mentoring others - Creative problem-solving, a keen eye for detail, and the ability to think through complex issues - Comfortable working directly with internal facing customers to understand needs/requirements and collaborate on solutions - A strong understanding of the Linux operating system - Strong technical knowledge of cloud infrastructure (especially GCP), distributed systems, and reliability practices - Deep experience designing, building, and running highly-available production infrastructure - Strong Golang or Python development experience; especially writing APIs to build, orchestrate and manage cloud infrastructure - Solid working knowledge of patterns and principles for designing and implementing cloud native applications on Kubernetes, such as Controllers and Operators - Robust knowledge of computer networking principles and extensive experience with cloud networking technologies to create scalable and secure environments - Extensive working experience with software and infrastructure monitoring tools (especially Datadog) - Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time Requirements - This role may require occasional travel for company events, team collaboration, or offsites Benefits - Base salary is just one component of Calendly’s total rewards package - All full-time (30 hours/week) employees are also eligible for our Top Performer Bonus program (or Sales incentive), equity awards, and competitive benefits

• Be an essential part of the team responsible for crafting and delivering creative cloud solutions for our clients. • Participate in technical envisioning, technical design, and delivery of assigned projects. • Execute the implementation of designed solutions into client deliverables. • Lead consultants in design and deployment of client workloads into Azure. • Provide technical expertise and support across the following areas of specialization: • Datacenter Transformation • Azure Infrastructure • DevOps and CI/CD pipelines • Cloud automation

• Manage SRE teams; • Technical excellence of teammates; • Implement and maintain monitoring solutions using Prometheus, Victoria-Metrics, and Grafana to identify and address performance issues proactively; • Manage logging infrastructure using Fluent, Fluent-bit, ElasticSearch, and Kibana, ensuring efficient log collection, analysis, and visualization; • Configure and manage alerting systems like AlertManager and Opsgenie to respond to critical incidents and minimize downtime promptly; • Control utilization of AWS Cloud services and design, deploy and manage scalable and highly available infrastructure; • Expertise in AWS services such as EC2, VPC, CloudWatch, and IAM to ensure optimal performance and security of our cloud-based applications; • Deploy and manage containerized applications using Kubernetes, Docker, and Helm, ensuring smooth orchestration and scalability; • Proficient in the Debian operating system, with the ability to troubleshoot and optimize system performance; • Implement and manage CI/CD pipelines using Jenkins and ArgoCD for seamless software delivery and infrastructure automation; • Manage code repositories using GitLab and Git, ensuring version control and collaboration among team members; • Collaborate with cross-functional teams using Jira and Confluence for effective project management and knowledge sharing.

• Own and develop the IVIX on-premise deployment architecture end to end, driving engineering decisions on how it is built, scaled, and improved over time • Execute complex deployments in client environments, working hands-on with Kubernetes, containerized services, networking, storage, and multi-component infrastructure configurations • Serve as the technical point of contact with clients from pre-onboarding through go-live, leading technical conversations, managing expectations, and handling any technical questions that arise throughout the deployment process • Translate RFP requirements and contractual specifications into structured installation plans, coordinating all moving parts and managing the deployment timeline end to end • Take full ownership of post-deployment technical operations: resolving infrastructure failures, networking and connectivity issues, and containerized service configurations across client environments