Staff Software Engineer, AI Systems

Company shown to members 🔒 · Remote · US, Canada only

US, Canada only6+ years required$215K–250K/yrPublished 21 September 2026Looks fresh

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First recorded by Psst: 12 October 2026. Your first 3 jobs are free to apply to (the first right away, 2 more with your email). After that, the company and the apply link are for Psst members, from $4.99 for 7 days.

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The 20-second read

Experience
6+ years required
Where you can live
US, Canada only
Skills and tools
python, typescript, b2b, saas

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Job details

Where you can work
United States, Canada
Employment type
Not stated by the employer
Advertised pay
$215K–250K/yr
Experience
6+ years required
Employer publication date
21 September 2026
First recorded by Psst
12 October 2026
Last checked at the source
10 November 2026

About the job

There's nothing more exciting than transforming an industry that's been stagnant for decades.

The company is an AI-native platform that’s bringing agentic AI to the full policy lifecycle. We’re aggressively transforming how insurance work gets done, and the world is paying attention: we've raised $180 million, including a $100 million Series D from Goldman Sachs. We have powerful product-market fit, and we're growing fast globally.

You'll get to work on complex problems with one of the most advanced AI teams you'll find anywhere. If you're the person we need, you know that AI bolted onto legacy systems is too weak to matter. That's why we built our platform to be AI-native from day one. That's why you can do here what you can never do at a legacy software company. move fast and prove it, not theorize it. We think from first principles. You’ll work on problems that matter, building software that fundamentally changes how insurance operates.

Role Overview

We are looking for an Software Engineer, AI Systems to help build the backend architecture behind our emerging agent systems. This role sits at the intersection of software engineering, data infrastructure, and applied AI. You will work across the stack to design and implement systems that power LLM-driven product capabilities — from orchestration and tool integration to evaluation and production deployment. You’ll collaborate closely with product managers, designers, and engineers to bring AI-powered workflows directly into our underwriting platform. This is a high-impact role with significant ownership over both experimentation and production implementation. This role is ideal for engineers who enjoy working across layers of the stack and are excited about shaping how agent systems operate inside real production software.

What You'll Be Doing

  • Design and implement agent workflows and orchestration systems for AI-powered product features
  • Build backend services that integrate LLMs with structured insurance data and platform APIs
  • Develop infrastructure for tooling, context management, and agent execution
  • Contribute to internal frameworks supporting prompt iteration, evaluation, and observability
  • Partner with product and design to translate underwriting workflows into AI-enabled product experiences
  • Help define architectural patterns for building reliable AI-native features in production
  • Work across backend systems, data infrastructure, and product integrations to ship user-facing capabilities

Who We Hope You Are

  • 6+ years of experience in backend engineering, data engineering, or related roles
  • Strong experience building production backend systems and APIs
  • Professional experience working with LLMs, agent systems, or generative AI applications
  • Hands-on experience with prompt design, tool-based agent architectures, or LLM workflows
  • Proficiency in Python or similar backend languages
  • Experience working with cloud infrastructure and distributed systems
  • Comfort working across layers of the stack, from infrastructure to product integration
  • Strong curiosity about emerging AI architectures and agent patterns
  • Comfortable navigating ambiguity and working in a fast-paced, collaborative environment

Bonus Points if...

  • Experience building production systems involving LLMs, agents, or prompt pipelines
  • Experience designing internal platforms or developer tooling
  • Familiarity with insurance, fintech, or B2B SaaS
  • Contributions to open-source AI or data infrastructure projects
  • Experience with Typescript

Why This Role Matters

You will help build the core infrastructure that powers the next generation of the company’s platform. Your work will shape how AI systems interact with underwriting workflows and how intelligent automation is delivered to customers. This is an opportunity to work on foundational architecture for agent-driven software, with real-world impact in one of the world’s largest industries.

Base Salary: $215,000 - $250,000 a year

Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above. Total compensation package includes stock options, benefits and additional perks.

Here at the company, your capabilities are important, but culture fit is essential. We move fast, are eager to listen to our users, take a first principles approach to solving problems, and value learning and the ability to change our minds. Most importantly, we're here to have fun. Our ability to make a difference starts with our people. We would love to work with you!

We are an equal-opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, sex, gender expression, sexual orientation, age, marital status, veteran status or disability status. We will provide reasonable accommodation to individuals with disabilities to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment. Please contact us to request accommodation at [link for members]

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