Engineering Manager

OhioX; Dublin, Northern (OH, KY); Hybrid; USD 150,000 - 195,000; Full time

Benefits offered by this job

Medical, Dental, and Vision

Flexible PTO Policy

401(k) with a company match

Employee Assistance Program

Parental Leave

Disability and Life Benefits

Job summary

Bold Penguin is the premier digital broker for commercial insurance. This remote Engineering Manager role leads a cross-functional team building AI-enabled systems, including an agentic chat, ensuring quality, cost, and reliability in production.

You will mentor engineers, conduct architecture reviews, and oversee recruiting to grow the team as products scale, while delivering robust software with a focus on performance and user impact.

Qualifications

• Proven track record shipping products and leading teams.
• Ability to decide team priorities in ambiguous situations.
• Experience with AI/LLM-backed systems in production.

Responsibilities

• Own what the team ships and decide priorities.
• Hands-on leader who can write/test code and review features for 4-10 engineers.
• Operate with ambiguity and make calls before data arrives.
• Lead and participate in code and architecture reviews.
• Own the agent in production: task completion, safe failure, escalation, cost and latency.
• Define autonomy boundaries for agent actions and human-in-the-loop decisions.
• Staff teams to meet objectives and recruit onboarding of new engineers.
• Mentor team members on unit testing, TDD, CI/CD, and linting.
• Coordinate complex technical activities with Product Managers.
• Mentor Tech Leads and contribute to design across the lifecycle.

Skills

Team leadership

LLM-backed systems

DevOps

Ruby on Rails

Angular

Python in AI context

Cloud architecture

CI/CD

Code reviews

Mentoring

Tools

Ruby on Rails

Angular

Python

Job description

• Location Remote - United States
• Base Pay $150,000.00 - $195,000.00 / Year
• Other Compensation Annual Performance Bonus Eligible
• Job Category People Management, Training & Mentorship, Hands-on Coding & Leadership
• Relocation Expense Covered No
• Employee Type FT Exempt
• Travel 5%
• Manage Others Yes
• Minimum Experience 8 Years

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.

Requirements

YOUR LOCATION

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

Skills & Experience

• 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.

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.

Summary

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

Stay connected to the Glacier.

We have great SLACK channels for work and play. We also like to video conference and hold all-hands "Waddles" regularly.

Penguin bling.

Like swag themed after a certain Antarctic bird? Just. You. Wait.

Bold Penguin believes in inclusion. That’s why we’re proud to be an equal opportunity employer that considers all qualified applicants regardless of race, color, religion, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. To learn more about our results-focused culture and employee-focused perks, read more on our careers page.