Founding Platform Engineer -- Ruby on Rails

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.

When we live these values, our product choices, customer interactions, hiring, and promotions all help us live out our mission: to build safer and more productive workplaces.

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., Leads complex, multi-workstream product initiatives as a principal Product Owner. Owns product vision, strategy, backlog integrity, prioritization, and Scrum team alignment. Coordinates Product, Engineering, Design, Delivery, and other stakeholders; improves execution discipline, transparency, and outcome tracking. Stabilizes programs with fragmented ownership or elevated delivery risk while ensuring customer and business requirements are addressed. Requires substantial Product Owner or Senior Product Manager experience, preferably in payments or financial services., Leads revenue recognition, billing, accounts receivable, collections, audit readiness, and financial controls. Owns ASC 606 compliance, billing systems, process automation, AI-enabled accounting improvements, reporting, and cross-functional alignment. Manages and mentors the accounting team while supporting scalable revenue operations and public-company readiness. Top Skills: Ai-Enabled Automation ToolsAsc 606GaapExcelMicrosoft OutlookMicrosoft WordNetSuiteOracleSAP

What you need to know about the Colorado Tech Scene

With a business-friendly climate and research universities like CU Boulder and Colorado State, Colorado has made a name for itself as a startup ecosystem. The state boasts a skilled workforce and high quality of life thanks to its affordable housing, vibrant cultural scene and unparalleled opportunities for outdoor recreation. Colorado is also home to the National Renewable Energy Laboratory, helping cement its status as a hub for renewable energy innovation.

Key Facts About Colorado Tech

• Number of Tech Workers: 260,000; 8.5% of overall workforce (2024 CompTIA survey)
• Major Tech Employers: Lockheed Martin, Century Link, Comcast, BAE Systems, Level 3
• Key Industries: Software, artificial intelligence, aerospace, e-commerce, fintech, healthtech
• Funding Landscape: $4.9 billion in VC funding in 2024 (Pitchbook)
• Notable Investors: Access Venture Partners, Ridgeline Ventures, Techstars, Blackhorn Ventures
• Research Centers and Universities: Colorado School of Mines, University of Colorado Boulder, University of Denver, Colorado State University, Mesa Laboratory, Space Science Institute, National Center for Atmospheric Research, National Renewable Energy Laboratory, Gottlieb Institute

• 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., Leads revenue recognition, billing, accounts receivable, collections, audit readiness, and financial control operations. Ensures ASC 606 and GAAP compliance, manages billing platforms and ERP integrations, drives automation and AI adoption, develops scalable processes, partners cross-functionally, reports financial metrics, and supervises accounting staff. Requires extensive revenue accounting and billing experience in SaaS or software, management expertise, and strong technical accounting knowledge. Top Skills: Ai-Enabled Accounting Automation ToolsBilling PlatformsErp SystemsExcelMicrosoft OutlookMicrosoft WordNetSuiteOracleSAP

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

• Stage 1 - Screen
• Recruiter Screening - 15 minutes
• Hiring Manager Screen - 30 minutes
• Stage 2 - “On-site” Loop

• Part 1 o Practical Coding - 60 minutes o System Design - 90 minutes

• Part 2 o Infrastructure & Operations Deep Dive - 45 minutes o Past Project Deep Dive & Technical Leadership - 45 minutes

• Final Interview
• CTO Meet & Greet - 30 minutes

Compensation & Benefits

• $163K - $185K + Bonus
• Competitive employer-sponsored health insurance
• 401(k) + company matching
• Professional development reimbursements
• Flexible, fully remote environment
• Quarterly remote work stipend

The EasyLlama herd is fully remote, with employees distributed across the US. We are currently hiring in the following approved states: AR - Arkansas CA - California CO - Colorado CT - Connecticut FL - Florida IL - Illinois LA - Louisiana MA - Massachusetts MI-Michigan MN - Minnesota NJ - New Jersey NY - New York NC - North Carolina OH - Ohio OR- Oregon PA - Pennsylvania TN - Tennessee TX - Texas VA - Virginia WA - Washington WI - Wisconsin

*EasyLlama reserves the right to change the list of approved states at anytime.

*To ensure the best employee experience, we offer competitive compensation packages, comprehensive benefits, an annual wellness stipend, PTO, 401k with company matching, and monthly team events to nurture connection!

At EasyLlama, we strive to walk the walk. We are helping make workplaces all over the globe safer and more inclusive, including our own. We honor employees and candidates from all walks of life and all experiences, regardless of race, ethnicity, veteran status, disability, sexual orientation, gender identity or religion. *Applies to full time (W2) employees.

Lead the creation of EasyLlama’s Platform Engineering function and technical roadmap. Build and operate scalable Ruby on Rails services, Kubernetes and AWS infrastructure, CI/CD pipelines, developer tooling, AI and LLM infrastructure, billing systems, enterprise integrations, and observability platforms. Drive security, reliability, scalability, and architectural decisions across engineering teams while mentoring engineers and resolving complex production issues. The summary above was generated by AI

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.