Lead Operations Engineer

About CacheFly: CacheFly powers fast, secure content delivery across the globe. We're a performance-driven, remote-first technology company that values ownership, accountability, and speed — and we hold our infrastructure to the same standard. Our global CDN serves customers who depend on us around the clock, which means the team behind it needs to be elite. We're small enough that every person has real impact, and serious enough about reliability that we never stop raising the bar. The Role: CacheFly is hiring the technical leader of our Operations team, the people who keep our global CDN platform running, fast, and reliable around the clock. This person will be a hands-on, technically elite operator who leads from the front and sets the standard by doing. You are the most capable operator in the room, deep in Linux systems, HTTP and caching internals, and the network itself, troubleshooting, tuning, automating, and resolving the hardest problems alongside the team rather than from a distance. The Operations team is the backbone of CacheFly’s CDN. The team runs the day-to-day platform, provision servers and PoPs, upgrade components and fleets, and manage service configuration across the network. We obsess over configuration consistency and continuously raising the performance baseline — finding bottlenecks and degradation before they become incidents. We also own customer support tickets and partner with pre-sales on proof-of-concept engagements. You will lead all of it. The full Operations team reports to you, and you report directly to the VP of Engineering. You’ll lead a team from day one as its technical anchor. Formal people management is not the focus of this role right now, but it will become part of the job as the role matures. We expect you to develop that muscle over time, with support from technical leadership and HR as you ramp. If you’ve never managed before but want to, this role is designed for that path. Key Responsibilities: Serve as the primary technical resource and senior escalation point for the Operations team. Work hands-on across all core responsibilities — provisioning, upgrades, configuration management, performance work, and customer support. Lead the response on large-scale incidents and oversee the handling of smaller ones. Own communication with large and strategic customers during incidents and escalations — clearly, calmly, and professionally under pressure. Author incident post-mortems and drive the actionable follow-ups and process improvements that come out of them. Continuously improve CDN reliability, performance, and operational excellence across the platform. On-call & Escalations: We provide 24/7 coverage for incidents and customer support, and you are the top technical link in the escalation chain. You will take escalations outside of normal working hours. Major incidents will reach you when they happen, not when it’s convenient. This is a defining part of the role, and we want candidates who go in clear-eyed about that. In exchange, you have a real escalation path of your own — you’re never carrying a major event alone. Escalation path is as follows: Operations team > Lead Operations Engineer > VP of Engineering > CTO. Who You Are: In-depth Linux system administration experience at scale. Deep understanding of HTTP and caching. Strong networking knowledge — routing and TCP/IP. Proven ability to troubleshoot and resolve complex, customer-facing issues. Ability to reverse-engineer system architectures with limited documentation and document them for the team. Clear, professional communication with customers under pressure. Hands-on experience with Nginx, HAProxy, Varnish, BGP, anycast, and CentOS / RHEL / Rocky Linux. Proficiency in a scripting language (Bash, Python, PHP, or similar). Experience operating in high-availability, latency-sensitive environments. Benefits: People-First Culture; While we’re obsessed with performance, we’re also deeply committed to taking care of our people through fair compensation, competitive global benefits, and a culture of mutual respect and authenticity. Competitive salary and annual bonus (15% target) Cutting-edge technology and resources to help you succeed in your role Remote-first culture Unlimited PTO and all National holidays off $3,000 work-from-home stipend, monthly internet/phone or coworking allowance Full health benefits (medical, dental, vision, LTD/STD, life) – most at no cost to you* 401(k) with 4% Safe Harbor company match, fully vested from day one* *Benefits marked with an asterisk (*) are available to U.S.-based employees. For team members outside the United States, equivalent value is incorporated into total compensation and country-specific benefits where applicable.