Engineering Lead, Systems Operations

About Us Chess.com is one of the largest gaming sites in the world and the #1 platform for playing, learning, and enjoying chess. We are a team of 600+ fully remote people in 60+ countries working hard to serve the global chess community. We are here to support 200M+ chess players worldwide with the best possible product, content, and tools to serve the community! We are a tech company. A gaming company. A content company. And we do it all with passion and commitment to the game. Above all we prize our mission-driven, flat, life-celebrating, no-corporate culture, and we look forward to meeting you and learning more about what you can bring to the team. About You You are passionate about building and managing infrastructure. It brings you joy to learn new technologies and use them to help reach challenging product goals. You have solid experience deep diving into Linux internals, as well as the future-oriented skills of managing Cloud/Kubernetes ecosystems. You are humble with a sense of humor and eager to be a part of a like minded team of people. You have been working in or dreamed of working in the gaming industry and are ready to turn your talents towards chess! What You’ll do Lead and mentor a team of 5-8 system operations engineers, providing technical guidance, career development, and performance management while demonstrating adaptive leadership styles and fostering a teachable culture of continuous learning Define and execute the multi-year SysOps strategy with clear prioritization of critical initiatives, including multi-regional infrastructure architecture capable of handling millions of concurrent sessions across global data centers Own the hybrid cloud migration roadmap, partnering with leadership to integrate bare-metal datacenter resources with cloud services for optimal performance and cost efficiency, delivering value through time-to-market optimization Establish on-call rotation policies and incident response procedures with strong focus on work-life balance, ensuring rapid resolution of critical system issues while maintaining team health and high availability SLAs Drive the implementation of monitoring, observability, and alerting systems that reach the right people at the right time, proactively identifying and resolving performance bottlenecks before they impact users and preventing organizational surprises Partner with engineering leadership to implement infrastructure-as-code practices and establish deployment pipelines that support continuous integration and delivery, emphasizing quality with high first-time-right rates and low rework Oversee capacity planning, load testing, and resource allocation strategies across distributed computing environments, demonstrating excellent time management and execution velocity while managing infrastructure budget and cost optimization Champion security protocols and risk assessment procedures for infrastructure components and data protection with unwavering integrity, ensuring compliance with industry standards and earning trust across the organization Collaborate with product and engineering leaders to design scalable solutions for high-traffic applications, valuing others' time by simplifying cross-team workflows and ensuring clear presentation of technical concepts to varied audiences Lead automation initiatives that deliver measurable value to both internal and external customers, reducing manual operational overhead and improving system reliability through scripting and configuration management Build authentic relationships with cross-functional teams and stakeholders, ensuring transparent communication of system health and aligning SysOps priorities with business objectives through excellent listening and presentation skills Recruit, retain, and develop top engineering talent by understanding individual motivations and aligning team goals with personal drivers, fostering an inclusive culture where growth mindset principles guide decision-makin ... (truncated, view full listing at source)