Founding Engineer

The Problem

Insurance agents spend their days doing tons of manual click work, copying and pasting into carrier forms, entering commission payouts into HR systems, and digging for the right pieces of information in 200-page policy PDFs.

Insure Stack is fixing that. We're building the AI-native operating system for insurance distribution - starting with automation that eliminates the most painful manual workflows, and working toward becoming the de facto platform for the industry.

The insurance brokerage and agency market in the U.S. alone generates over $150B+ in annual revenue. It's massive, it's essential, and the tooling is years behind what modern AI makes possible. The opportunity to rebuild this from the ground up is wide open.

Why Insure Stack

We're not guessing at product-market fit. Insure Stack is the acquisition of a YC company, led by operators with ~50 years of collective insurance industry experience. The distribution network is already in place - 800+ agency customers from day one. Sister companies in the portfolio serve as a built-in incubation lab to test every hypothesis with willing, knowledgeable users.

The bottleneck is not distribution, not domain expertise, not customer access. It's engineering execution. That's where you come in.

The Role

You'd be joining as a founding engineer working with a YC-alum CTO (ex-FAANG, multi-time founder). The intent is to build a small team of high-leverage engineers who each own large surface areas of the product and ship autonomously.

This means:

You own features end-to-end. There is no product spec handed to you - you'll shape what gets built and how.
You operate with minimal process and maximum velocity. The philosophy is simple: take shots on goal. Ideas are cheap to test, especially with AI.
There are no closed doors. You’ll have access to speak directly with the customers and leadership of our customers to learn about their pain points directly.
You may be the last engineer we hire. The team stays small and leveraged by design.

Some examples of what you’d work on:

AI agents that fill out carrier quoting forms so agents can focus on selling instead of data entry. This involves Playwright-based browser automation navigating real, messy carrier portals.
Document intelligence pipelines that process hundreds of pages of policy documents and distill them into what actually matters for a sale.
The foundation of an AI-native CRM where insurance agencies can spin up AI agent teams to handle the tedious operational work that currently eats their day.
New verticals we have many more ideas about valuable products for insurance agents than engineers to build them.
Fully remote for the right person.

You should be strong in
Python and Next.js - our core stack
Playwright / browser automation - central to the carrier portal work
Working with LLMs - how do we make AI pipelines fast, accurate, and cost-efficient
AI coding - how can we build 10x faster with the same resources

You might thrive here if
You default to shipping. Ambiguity doesn't slow you down, it's your operating environment.
You take ownership without being asked. If something is broken or unclear, you fix it or figure it out.
You're senior or staff-level in judgment, not just title. No formal years requirement, but you need to operate independently against ambiguous problems with minimal guidance.
You find it genuinely exciting to build something transformative in an industry that's running 20+ year old ancient software.
You want to be one of the key people in taking over the insurance industry. We have the reach, we just need builders now.
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