YOUR ROLE

Engineering Managers work as part of a cross-functional product team to build & launch products that remove the friction from commercial insurance. You'll lead and manage a team of first class software developers that will rely on you to ensure their decisions and work have the full support of the company. Your team builds and operates AI-enabled systems, including an agentic chat experience running against real submission and policy data. You'll own their quality, cost, and reliability in production. Your users will be small business owners who will use your work to understand, compare, and buy the commercial insurance their business needs. This is a self-serve purchase experience, and conversion is the measure of whether it works.

WHAT YOU'LL DO

• 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.

• 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.

NICE TO HAVE

• 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 is a plus, not a requirement.

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.

Benefits

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