Founding Platform Engineer

About EasyLlama

EasyLlama is on a mission to end checkbox compliance. We started by reinventing compliance training with engaging, bite-sized, mobile-first learning instead of outdated, one-size-fits-all courses. Today, we're building an AI-powered Human Risk Management platform that helps organizations reduce risk through modern training, policy management, phishing simulations, and intelligent automation. Our goal is to help companies build compliance programs that are effective, measurable, and built for the way people work today.

More than 6,000 organizations, including Shake Shack, WeightWatchers, Sephora, Jiffy Lube, and Y Combinator, trust EasyLlama. We're proudly bootstrapped, profitable, and recognized on the Inc. 5000 list, with a 96% G2 rating and industry-leading NPS and CSAT scores. We move quickly, value ownership and collaboration, and believe the best ideas come from people who are excited to solve meaningful problems and make a real impact.

Our CORE values are DRIVE: Doers, Resourceful, Impactful, Valued Partners, & Excellence-Focused.

• We are Doers. We proactively make things happen.
• We are Resourceful. We treat time, money, and energy as valuable.
• We are Impactful. We prioritize what matters.
• We are Valued Partners. We put customers & teammates first.
• We are Excellence-Obsessed. We always deliver excellent work.

From CEO to newest hire, DRIVE asks us to take ownership, solve problems, prioritize what matters, support teammates, and deliver high-quality work.

About the Role

This is a Founding Platform Engineering role at EasyLlama. You’ll be the first dedicated platform engineer, responsible for building the technical foundation that powers our products and enables every engineering team to move faster. You’ll partner closely with the CTO and Sr Engineering Manager to define the vision, architecture, and roadmap for Platform Engineering.

Over time, you’ll help build and shape a dedicated Platform Engineering squad, establishing the team’s technical direction, standards, and culture. This is a unique opportunity to build both the platform and the organization from the ground up.

As our most senior individual contributor, you’ll remain deeply hands-on while owning the core systems that every engineer depends on, including:

• Billing and payments
• Enterprise integrations and APIs
• Kubernetes infrastructure and cloud architecture
• CI/CD and developer experience
• AI platform and LLM infrastructure
• Observability, monitoring, and reliability
• Platform security and scalability

If you enjoy solving difficult technical problems, building systems that scale, and enabling other engineers to be more productive, we’d love to talk.

What You'll Do

• Own the technical roadmap for Platform Engineering.
• Architect, build, and operate highly scalable backend services using Ruby on Rails.
• Design and operate our Kubernetes infrastructure, cloud architecture, and deployment pipelines.
• Improve developer productivity through CI/CD, automation, internal tooling, and engineering best practices.
• Build and evolve the platform powering our AI products, including LLM orchestration, agent infrastructure, prompt management, evaluation pipelines, model routing, and AI observability.
• Own our billing platform, including subscriptions, licensing, payments, usage metering, invoicing, and Stripe integrations.
• Design and maintain secure, scalable integrations with HRIS platforms, identity providers, and enterprise customers using REST APIs, OAuth, SAML, SCIM, and webhooks.
• Build best-in-class observability through logging, metrics, tracing, alerting, and performance monitoring.
• Improve the scalability, security, reliability, and operational excellence of our platform.
• Lead architectural decisions that impact multiple engineering teams.
• Mentor engineers through technical leadership, design reviews, and engineering best practices.
• Diagnose and resolve complex production issues across infrastructure, applications, and distributed systems.
• Help establish and grow the Platform Engineering function as EasyLlama scales.

Who You Are

• 10+ years of professional software engineering experience.
• Expert-level Ruby on Rails experience building production SaaS applications.
• Strong React experience and the ability to work across the full stack.
• Extensive experience designing distributed systems and service-oriented architectures.
• Deep experience with Kubernetes, Docker, AWS, and cloud-native infrastructure.
• Strong experience building and operating CI/CD pipelines and modern developer tooling.
• Experience owning production infrastructure with high availability and reliability requirements.
• Experience designing and maintaining APIs and enterprise integrations.
• Strong understanding of SQL, database design, caching, background processing, and notification systems like email and SMS.
• Experience leading complex technical initiatives across multiple teams without direct people management.
• Excellent debugging, communication, and architectural design skills.
• A builder’s mindset with strong ownership and a passion for creating platforms that enable other engineers to move faster.

Nice to Have

• Experience building AI-native products or internal AI platforms.
• Experience with LLMs, AI agents, prompt engineering, RAG, vector databases, and evaluation frameworks.
• Experience with Stripe or other subscription billing platforms.
• Experience with Infrastructure as Code (Terraform, Helm charts, etc.).
• Experience with event-driven architectures and distributed messaging systems like RabbitMQ, SQS, or NATS.
• Experience working at a high-growth B2B SaaS company.
• Experience with SOC 2, cloud security, and compliance best practices.
• Open-source contributions or a track record of technical thought leadership.