Staff/Principal DevOps Engineer

Location: Remote (Lexington, KY Preferred)
Engagement: Full-Time

About Us – Scaling the Future of Fractional Ownership

Experiential Squared (E2) is pioneering fractional ownership in sports and beyond. Our flagship platform, MyRacehorse (MRH), is the largest fractional thoroughbred ownership platform in the world, with 100,000+ passionate owners and over 200 race wins, including the Kentucky Derby, Preakness, and Breeders’ Cup Classic.

We are at a pivotal moment, scaling beyond horse racing and simultaneously elevating the MRH platform. As we modernize our stack and launch new products, the reliability, security, and scalability of our infrastructure are paramount. To lead this effort, we need a technical cornerstone—a DevOps leader who will take deep ownership of our platform's foundation.

The Role – Own Our Reliability & Developer Velocity

This is a hands-on technical ownership role, not a people management position. As our first Staff/Principal DevOps Engineer, you will be the most senior individual contributor focused on infrastructure, security, and developer enablement. You will be the go-to expert for ensuring our systems are scalable, secure, and reliable. You will spend your time architecting cloud infrastructure, building robust CI/CD pipelines, and creating tools that empower our software engineers to ship code faster and more safely.

Your Mission (Responsibilities):

• Architect and Own Our Cloud Infrastructure: Design, build, and manage a scalable, secure, and cost-effective cloud infrastructure (AWS/GCP/Azure). You will own our Infrastructure as Code (IaC) using tools like Terraform or CloudFormation.

• Build a World-Class CI/CD Engine: Create and maintain robust, automated CI/CD pipelines for our entire tech stack, including our Next.js frontend, Capacitor mobile builds, and Magento (PHP) backend. The goal is fast, reliable, and safe deployments.

• Stabilize and Secure the Core Platform: Take ownership of the hosting environment for our critical Magento e-commerce platform. Implement best practices for performance tuning, security hardening, and zero-downtime deployments.

• Champion Observability and Reliability: Implement and manage a comprehensive observability strategy using tools for logging, monitoring, tracing, and alerting (e.g., Datadog, New Relic, Prometheus/Grafana). Define SLOs/SLIs to ensure platform health.

• Automate Everything: Drive a culture of automation across the engineering organization. Identify bottlenecks in development and operational workflows and build solutions to eliminate them.

• Lead Infrastructure Security & Compliance: Partner with the engineering team to implement and automate security best practices at every layer of the stack. Ensure our infrastructure meets the stringent requirements for compliance and cyber insurance.

• Elevate the Developer Experience (DevEx): Be a force multiplier for the engineering team by improving local development environments, streamlining build processes, and providing self-service tools that make their jobs easier.

Who You Are (Qualifications):

• A Proven Senior DevOps/SRE: You have significant experience as a Senior, Staff, or Principal DevOps or Site Reliability Engineer, with a track record of owning the infrastructure for a high-growth product.

• Cloud and IaC Expert: You possess deep, hands-on expertise with a major cloud provider (AWS preferred) and have mastered Infrastructure as Code with Terraform or a similar tool.

• A CI/CD Master: You have extensive experience designing, building, and maintaining sophisticated CI/CD pipelines using tools like GitHub Actions, GitLab CI, or Jenkins.

• Containerization Pro: You are highly proficient with Docker and have production experience with container orchestration platforms like Kubernetes (EKS/GKE) or ECS.

• Pragmatic with Legacy Systems: You have experience supporting and migrating legacy applications. Specific experience with the PHP/Magento ecosystem is a massive plus.

• Security-First Mindset: You instinctively build security into your designs and have experience with infrastructure security tools, vulnerability scanning, and implementing compliance controls.

• An Observability Advocate: You believe "if you can't measure it, you can't improve it" and have experience building rich observability dashboards and actionable alerts.

• A Force Multiplier: You thrive on making the entire engineering team more productive and effective. You are an excellent communicator and collaborator.

Why Join Us?

• Be the Infrastructure Cornerstone: This is a chance to be the foundational infrastructure leader at a rapidly growing company, with immense impact on our technical direction and stability.

• Massive Impact: Your work is the bedrock upon which our entire platform is built, enabling a product used by a huge, passionate, and engaged community.

• Solve Hard Problems: From scaling a high-traffic e-commerce platform to building deployment pipelines for a modern stack, you'll tackle challenging and rewarding infrastructure problems every day.

• Build the Foundation: You won't just maintain systems; you will architect the scalable and secure foundation that allows us to innovate and shape the future of fractional ownership.

Compensation & Benefits

• Competitive salary & comprehensive health, dental, and vision benefits.

• Flexible remote work environment.

• Employee Perks

• Discretionary Time Off Plan (Get your work done, and then take time to relax and recharge)

• Paid Holidays