Outmarket

Principal Software Engineer

United States · Remote (country restricted) · FullTime

Apply on the employer’s site ↗See how well you match this job

You apply directly with the employer. ROLIVA does not submit applications from this page and is not the employer.

About the role

Description from the employer’s posting. Check the employer’s page for the current version.

EmployerOutmarket
LocationUnited States
Work styleRemote (country restricted)
Employment typeFullTime
Employer posted3 months ago

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

A high-impact role with ownership from day one.

Show full description

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 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

- Define the long-term technical vision for an AI-native insurance platform.

- Make the decisions that shape the product's foundation for years.

- Work shoulder-to-shoulder with founders on company-defining problems.

WHAT YOU'LL 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.

WHAT WE'RE LOOKING FOR

- 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.

BONUS IF YOU HAVE

- Deep experience with production AI/ML systems or large-scale data platforms.

- Founding or early-stage technical leadership experience.

See how well you match this job Apply on the employer’s site ↗

Check your resume against this job Free, no sign-up. Nothing you paste is stored.

Staying safe while you apply

Never pay to apply, interview or accept an offer. ROLIVA never asks you for payment to apply to a job.
Apply only through the official “Apply on the employer’s site” button, on the employer’s own site, and check that a recruiter’s email uses that employer’s own domain rather than a free email address.
Be cautious of an offer made with no real interview, or pressure to decide quickly or share financial details early.

Does something look wrong with this listing? Use “Report broken link” in the role details, or read ROLIVA’s full job-safety guidance ↗.

Preparing for this role with ROLIVA

Check the fit.
Compare the requirements with the experience you have confirmed, including gaps.
Prepare honestly.
Build interview stories and application drafts from your own evidence.
Keep track.
Save the role and record your own application status and follow-ups.

Create a free workspace or log in.