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Bold Penguin

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Staff Software Engineer - Ruby on Rails

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Summary

Staff engineer at insurtech Bold Penguin leading the architecture of complex, highly scalable solutions while staying a hands-on individual contributor. Core stack is Ruby on Rails with cloud-native, CI/CD-driven delivery, plus AI/LLM work such as RAG pipelines, agentic workflows, and vector databases.

YOUR ROLE

In your role as a staff engineer you will be tasked with solving our hardest problems by leading and architecting complex, highly scalable solutions; along with performing as a strong individual contributor on the team.

At this point in your career, you will have had a broad range of technology acumen as well as a depth of experience in more than one area. You will have a significant impact on the engineering organization itself by helping advance Bold Penguin’s software engineering discipline.

WHAT YOU'LL DO

  • Engage across product teams to plan, coordinate, architect, and deliver high-complexity features

  • Ensure that solutions are built with security, performance, and fault-tolerance in mind

  • Be an expert in modern cloud architecture and concepts in software engineering such as continuous integration, continuous delivery, DevOps, and site-reliability engineering

  • Collaborate with product managers, designers, site-reliability engineers, and customers to build powerful, impactful products

  • Participate in the full lifecycle of the software development life cycle from ideation to delivery

  • Mentor more junior engineers in areas such as unit testing, continuous integration, DRY/SOLID principles, SDLC, etc. to facilitate career growth on the team

  • Other duties and responsibilities as assigned.

  • Engage across product teams to plan, coordinate, architect, and deliver high-complexity features

  • Ensure that solutions are built with security, performance, and fault-tolerance in mind

  • Be an expert in modern cloud architecture and concepts in software engineering such as continuous integration, continuous delivery, DevOps, and site-reliability engineering

  • Collaborate with product managers, designers, site-reliability engineers, and customers to build powerful, impactful products

  • Participate in the full lifecycle of the software development life cycle from ideation to delivery

  • Mentor more junior engineers in areas such as unit testing, continuous integration, DRY/SOLID principles, SDLC, etc. to facilitate career growth on the team

  • Other duties and responsibilities as assigned.

YOUR LOCATION
This is a fully remote role, with the exception of onboarding and optional in-office events.

SKILLS AND QUALIFICATIONS

  • 10+ years of professional engineering experience

  • 5 years of technical experience with Bold Penguin technologies

  • Previous working experience in high-growth technology companies and/or startups

  • Ability to articulate very complex technical concepts to technical and non-technical people

  • Experience building highly resilient, cloud-native applications

  • Full-stack expertise in multiple tiers of modern web applications (e.g., front end, back end, infrastructure, etc.)

  • Bonus points for open-source contributions and/or speaking experience.

  • Working experience in high-growth technology companies or startups is very desirable.

RUBY/RAILS REQUIREMENTS

  • Knowledge of microservice architectures and RESTful APIs
  • Progressional experience with Ruby on Rails.
  • Understanding of scrum, unit testing, continuous integration, continuous delivery, and DevOps a plus.

AI/LLM QUALIFICATIONS

  • Write clean, well-tested, and secure code, applying DRY/SOLID principles to both traditional Rails features and non-deterministic AI/LLM outputs.
  • Build internal component libraries that ensure a great user experience, adapting design systems to handle dynamic, AI-generated insights and agentic workflows.
  • Experience building with orchestration frameworks, RAG pipelines, or autonomous agents, with a solid grasp of handling vector databases and non-deterministic outputs.
  • Strong working knowledge of microservice architecture, secure RESTful APIs, and cloud infrastructure, ensuring traditional code and AI features play nice together.

PHYSICAL REQUIREMENTS
  • Must be able to sit/stand/walk for prolonged periods of time (up to 8 hours per day), at a desk working on a computer.
  • Must be able to use standard office equipment for extended periods of time, including but not limited to, a mouse, keyboard, phone and video conferencing.

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