Staff Software Engineer, Platform

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 We started by reinventing compliance training with engaging, bite-sized, mobile-first learning instead of outdated, one-size-fits-all courses.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.

• 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.
  

• 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.

The interview process takes about 3 weeks and may include cross-functional stakeholders.

• Recruiter Screening - 15 minutes

• Hiring Manager Screen - 30 minutes
  

• Part 1

  • Practical Coding — 60 minutes

  • System Design — 90 minutes

• Part 2

  • Infrastructure & Operations Deep Dive — 45 minutes

  • Past Project Deep Dive & Technical Leadership — 45 minutes

• CTO Meet & Greet — 30 minutes