Principal Software Engineer
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At a glance
Job overview
Outmarket.AI is hiring a Principal Software Engineer. Outmarket is seeking a Principal Engineer to define the technical direction for its AI-native platform. This role involves owning architecture and technical strategy, making high-stakes engineering decisions, and acting as a force multiplier across the organization. The Principal Engineer will work closely with founders to shape the product's foundation and mentor other engineers.
Key focus areas include Own architecture and technical strategy across AI, data, infrastructure, and product, Drive the most consequential and ambiguous technical decisions to resolution, and Establish engineering principles and standards adopted org-wide.
Successful candidates bring 10+ Years Engineering Experience. Important skills include Org-Wide Technical Leadership, System Design, Architecture At Scale, Hands-On Ability, Technical Bets, and Exceptional Judgment. Preferred (not required): Production AI/ML Systems, Large-Scale Data Platforms, Founding Technical Leadership, and Early-Stage Technical Leadership.
Skills & qualifications
Skills
Qualifications
Full job description
ABOUT OUTMARKET
Outmarket is the AI platform for insurance, trusted by more than 250 brokerages to run the work their business depends on. Commercial insurance still runs on dense documents and slow, manual workflows, and that is exactly what we automate: quote comparisons, coverage gap and tower analysis, policy review, and proposal generation, all grounded in our customers’ own data and source-cited so teams can trust the output.
The impact is concrete. Teams save 12 to 15 hours per person every week, cut errors by roughly 65 percent, and win more business, all on infrastructure that is SOC 2 Type II certified, single-tenant, and never used to train AI models. We are an AI-first company in both what we build and how we work, shipping quickly and in close partnership with the agencies that rely on us.
WHAT YOU’LL GET
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A high-impact role with ownership from day one.
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Competitive compensation and meaningful equity.
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Direct collaboration with founders and real users.
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Remote-first flexibility.
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The opportunity to help build an AI-native product from the ground up.
ABOUT THE ROLE
We are hiring a Principal Engineer to set technical direction at the company level. You will own the architecture and technical strategy for our AI-native platform, make the highest-stakes engineering decisions, and serve as a force multiplier across the entire organization.
WHY THIS ROLE
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Define the long-term technical vision for an AI-native insurance platform.
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Make the decisions that shape the product's foundation for years.
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Work shoulder-to-shoulder with founders on company-defining problems.
WHAT YOU'LL DO
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Own architecture and technical strategy across AI, data, infrastructure, and product.
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Drive the most consequential and ambiguous technical decisions to resolution.
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Establish engineering principles and standards adopted org-wide.
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Mentor staff and senior engineers and elevate the whole team's technical judgment.
WHAT WE'RE LOOKING FOR
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10+ years of engineering with a record of org-wide technical leadership.
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Mastery of system design and architecture at scale, with deep hands-on ability.
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History of making high-stakes technical bets that paid off.
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Exceptional judgment, communication, and the ability to align teams on direction.
BONUS IF YOU HAVE
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Deep experience with production AI/ML systems or large-scale data platforms.
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Founding or early-stage technical leadership experience.
You've read the whole posting — now see how you match it.