Principal Software Engineer

The role

The Principal Engineer will own the architecture and technical strategy for an AI-native platform. This role involves making high-stakes engineering decisions and setting technical direction across AI, data, infrastructure, and product.

What you will do

• Own architecture and technical strategy across AI, data, infrastructure, and product
• Drive the most consequential and ambiguous technical decisions to resolution
• Establish engineering principles and standards adopted org-wide
• Mentor staff and senior engineers and elevate the whole team's technical judgment

Required qualifications

• 10+ years of engineering with a record of org-wide technical leadership
• Mastery of system design and architecture at scale, with deep hands-on ability
• History of making high-stakes technical bets that paid off
• Exceptional judgment, communication, and the ability to align teams on direction

Nice to have

• Deep experience with production AI/ML systems or large-scale data platforms
• Founding or early-stage technical leadership experience

Benefits

• A high-impact role with ownership from day one
• Competitive compensation and meaningful equity
• Direct collaboration with founders and real users
• Remote-first flexibility
• The opportunity to help build an AI-native product from the ground up

About the company

Outmarket is the AI platform for insurance, trusted by more than 250 brokerages to run the work their business depends on. It is an AI-first company that automates quote comparisons, coverage gap and tower analysis, policy review, and proposal generation.