Outmarket AI
InsuranceDirect Ashby career site

Staff Software Engineer

Location
Remote (US)
Job type
Full-time
Level
Lead / Staff
Experience
7+ years
Listed
30 days ago

Skills & highlights for this role

  • system design
  • distributed systems
  • AI/ML systems

Also useful

  • large data platforms

What You’ll Get

  • 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 Role

We are hiring a Staff Software Engineer to provide technical leadership across teams without stepping out of the code. You will drive architecture for our most important systems, de-risk hard problems, and multiply the output of the engineers around you.

Why This Role

  • Set the technical direction for systems that the whole product depends on.
  • Solve the hardest cross-cutting problems in an AI-native platform.
  • Influence how the entire engineering org builds, without managing people.

What You’ll Do

  • Lead architecture for major systems spanning AI, data, backend, and frontend.
  • Identify and remove the biggest technical risks and bottlenecks.
  • Set engineering standards (design, testing, reliability, performance) and make them stick.
  • Mentor senior engineers and raise the technical bar across teams.

What We’re Looking for

  • 7+ years of software engineering, with a record of leading complex, cross-team systems.
  • Deep system design expertise and strong hands-on coding ability.
  • Demonstrated technical influence beyond your own direct work.
  • Sound judgment about trade-offs, scope, and what to build vs. defer.

Bonus If You Have

  • Experience scaling AI/ML systems or large data platforms.
  • Early-stage startup or 0>1 product experience.

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.

Read the original posting

From Outmarket AI's careers page, first listed on Rolev.ai on October 10, 2026. Rolev.ai is not the employer.

How Rolev.ai helps with this application

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Common questions

Where is the Staff Software Engineer job at Outmarket AI located?

Yes, this Staff Software Engineer opening at Outmarket AI is listed as Remote (US). Always check Outmarket AI's application page for specific state eligibility or relocation policies.

What qualifications are required for Staff Software Engineer at Outmarket AI?

For the Staff Software Engineer role, Outmarket AI highlights 7+ years of relevant experience; experience with system design, distributed systems, AI/ML systems. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.

How do I apply for the Staff Software Engineer position at Outmarket AI?

This listing links directly to Outmarket AI's Ashby application page. You can apply directly on Outmarket AI's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Ashby application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.