• Work with a team of highly skilled Staff and Senior Engineers • Evolve and optimize our hybrid AWS and bare metal infrastructure to securely run sandboxed code and AI Agents with industry leading cost efficiency • Investigate customer and infrastructure problems down to the packet capture and process memory level together with the team to ensure customers can trust Checkly • Contribute to infrastructure reliability and ensure systems stay snappy for ad hoc and scheduled workloads without breaking or exploding costs • Collaborate with product engineers to improve developer experience, support our strong shipping culture and provide observability they need

• Work with a team of highly skilled Staff and Senior Engineers • Evolve and optimize our hybrid AWS and bare metal infrastructure to securely run sandboxed code and AI Agents with industry leading cost efficiency • Investigate customer and infrastructure problems down to the packet capture and process memory level together with the team to ensure customers can trust Checkly • Contribute to infrastructure reliability and ensure systems stay snappy for ad hoc and scheduled workloads without breaking or exploding costs • Collaborate with product engineers to improve developer experience, support our strong shipping culture and provide observability they need

• Administer and maintain mission-critical Windows and Linux servers in virtualized (VMware, Hyper-V) and cloud (Azure, AWS) environments • Develop and maintain scripts (PowerShell, Bash, or Python) to automate tasks, improve system performance, and streamline operational workflows • Configure, deploy, and support Windows and macOS desktop systems, ensuring optimal performance and consistent user experiences • Troubleshoot endpoint, connectivity, and authentication issues by analyzing logs, configuration data, and network traffic • Collaborate with network engineers to monitor and maintain connectivity, resolving LAN/WAN/Wi-Fi issues as they arise • Support AV systems and classroom technology, ensuring seamless integration of instructional and collaboration tools for campus environments • Participate in user access and permissions management, maintaining secure, compliant data access for managed services clients • Monitor systems using tools such as ConnectWise, SolarWinds, or similar platforms; identify issues and escalate complex problems to senior team members when necessary • Follow security best practices in all system and network configurations, applying updates and patches in compliance with FERPA, GLBA, and institutional standards • Assist with periodic security audits, documenting findings and corrective actions to maintain compliance • Maintain detailed and accurate infrastructure documentation, including system configurations, troubleshooting procedures, and setup processes • Provide day-to-day leadership, coaching, and performance management for the Network Administrator and two Desktop Technicians, fostering collaboration and accountability across the team • Ensure consistent service delivery, prioritization of tasks, and professional development for team members • Support administrative and operational tasks such as inventory management, vendor coordination, and IT reporting • Demonstrate strong soft skills, including communication, teamwork, organization, and adaptability in a client-focused environment • Occasional travel to client sites, as needed

• Serve as a technical lead responsible for designing, securing, and operating enterprise infrastructure across on-premises, hybrid, and cloud environments • Ensure availability, performance, and security of Epic and third-party healthcare systems • Administer and secure Windows and Linux servers, Active Directory, DNS, DHCP, and identity platforms • Manage virtualization environments (VMware, Hyper-V) • Implement and maintain enterprise backup, disaster recovery, and business continuity solutions • Support vulnerability remediation, security incident response, and root-cause analysis • Automate infrastructure and security operations using scripting and configuration management tools • Partner with cloud, network, security, and application teams to deliver secure, resilient infrastructure