Engineering Manager

Bold Penguin builds digital products for commercial insurance. The Engineering Manager leads a cross-functional software team building and operating AI-enabled systems, including an agentic chat experience, and is accountable for their production quality, cost, reliability, and contribution to the self-serve purchase experience.

Responsibilities:

• Own what the team ships, including deciding what gets built when priorities are not handed down
• Be a hands-on leader who can write & test code, review features, and direct the technical activities for 4-10 other engineers
• Operate with ambiguity. Requirements will be unclear and scope will change, and you'll make calls before all the data arrives
• Lead and participate in code and architecture reviews
• Own the agent in production: task completion, safe failure, escalation to a human, and cost and latency across the full multi-call pipeline
• Set the autonomy boundaries. Decide what the agent does unattended and what requires a human in the loop, and be accountable for where you drew the line
• Ensure that teams are staffed to meet objectives; actively participate in the recruiting and onboarding of new engineers to meet growing demands
• Embody best practices and good work habits; mentor team members on engineering concepts such as unit testing, TDD, continuous integration, and linting
• Coordinate complex technical activities, define high-level milestones, and track progress towards objectives in conjunction with Product Managers
• Mentor Tech Leads on your team and participate in the design and development of complex software, through all phases of the software development lifecycle
• Other duties and responsibilities as assigned

Requirements:

• A track record of shipping, with specific products you can point to and say you launched
• Comfort operating without close direction, including deciding what the team works on when priorities are not handed down
• Previous technical leadership or management experience in technology startups
• Experience shipping and operating LLM-backed systems in production, not prototypes
• Experience with agentic systems in production, including multi-step tool use, session state, and evaluating a pipeline rather than a single call
• Firm grasp of DevOps, Agile, CI/CD, code quality, and cloud architecture
• Proficiency in Ruby on Rails, Angular, or comparable, plus working familiarity with Python in an AI or data context
• The ability to straddle both high level milestones and low level technical details
• A strong desire to promote a healthy working environment
• Experience with direct-to-consumer or e-commerce products, including conversion funnels, checkout and payment flows, and experimentation
• Understanding of data governance, PII, and auditability constraints when regulated data flows through third-party model providers
• Experience leading a team that uses AI coding tools, with a point of view on review standards
• Previous experience working in high-growth tech startup companies
• Commercial insurance experience