Principal Engineer, AI-Enabled Engineering

Job Overview

Principal Engineer, AI-Enabled Engineering

THE ROLE:  

At Polly, we've created the future of car insurance. Our innovative mobile technology enables car-buyers to view multiple insurance quotes and immediately purchase online and/or connect with licensed insurance agents. This is all powered by our people. We are bold trailblazers who are passionate about doing amazing things – together. If this sounds like you, we’d love to hear from you!

WHAT YOU’LL DO:  

Our engineering team is hiring a principal-level engineer who combines strong technical skills with a “can-do” attitude, who continuously thinks about quality and modern engineering practices.  The most qualified candidates will exhibit the following competencies and work attributes:

Technical depth

• Expert-level proficiency in C# / .NET is strongly preferred. We will consider exceptional Java engineers with a demonstrated ability and appetite to move into a .NET-dominant environment
• Experience designing and building distributed, cloud-native systems (Azure preferred)
• Strong API design, microservices, and event-driven architecture experience
• Hands-on with AI/ML integration

AI-enabled engineering mindset

• Demonstrated use of AI tooling to accelerate software delivery
• Experience building AI-assisted or AI-augmented features into production systems
• Passion for exploring how emerging tech changes the practice of engineering, not just the product
• Comfortable operating in ambiguity

Engineering leadership & maturity

• Proven track record of maturing engineering teams
• Establishes engineering standards and practices that stick across teams and outlast their direct involvement
• Coaches engineers at all levels and leads by example  
• Creates a culture of continuous improvement through direct, constructive conversations about quality and craft

Cross-functional influence

• Ability to translate complex technical concepts into clear guidance for engineers, product, and business stakeholders
• Works fluidly across product, data, and business teams
• Influences without authority

The Polly signal

• Excited by the opportunity to reshape how an industry operates through software
• Bias toward action and shipping
• Comfortable with ambiguity and fast-moving environments where the answer isn't always obvious

WHAT YOU NEED TO SUCCEED:  

Key Technical Experience

• Strong backend and/or frontend development (C#, .NET, React, Python, or similar).
• Experience with cloud platforms (Azure preferred) and microservices architecture.
• Proven experience with automated testing, CI/CD pipelines, and observability/monitoring.

WORK AND LIFE BALANCED, WE’RE HERE FOR YOU:

• Medical, dental and vision insurance 
• HSA, FSA, Dependent Care FSA and Commuter pre-tax benefit 
• Flextime PTO and generous holiday time 
• Paid Parental leave + baby cash 
• Matching 401(k) contributions 
• Employer paid Life Insurance
• Life & disability Insurance 
• Work from anywhere options 

Polly is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, gender, national origin, age, genetic information, creed, marital status, sexual orientation, gender identity, disability status, protected veteran status, or any other protected status as defined by federal, state or local law.

About Polly

Polly is the most trusted and complete digital insurance marketplace for automotive retailers and their valued customers. The company’s innovative mobile technology enables car-buyers to view multiple insurance quotes and immediately purchase online and/or connect with licensed insurance agents to complete the process. With an exclusive combination of partnerships among premier automotive retailers and data providers, an industry-best insurance carrier network, and access to Polly Insurance licensed agents, Polly is recognized for its place at the forefront of Insurtech. Polly Insurance is a licensed insurance agency, with licenses to operate in the lower 49 states.

Salary Minimum $155,000 +