Staff Software Engineer - Ruby on Rails

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.

• 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.

We offer competitive compensation and progressive benefits that include:

• Medical, Dental, and Vision
• Flexible PTO Policy
• 401(k) with a company match
• Employee Assistance Program
• Parental Leave
• Disability and Life Benefits

Bold Penguin is the premier digital broker for commercial insurance. Their technology expands top-of-funnel demand and increases yield for enterprise partners. Through digital distribution, wholesale capabilities, and AI-driven insights, they transform the lifecycle of both simple and complex risks, from prospecting to placement.