Shepherd (Series B) | ONSITE | San Francisco, CA & New York City, NY

At Shepherd, we're pursuing the most ambitious technical vision in commercial insurance: fully autonomous underwriting. Shepherd is an AI-native commercial insurance platform transforming how high-hazard industries get covered.

The infrastructure behind the AI boom (data centers, semiconductor fabs, renewable energy assets) has to be built and insured, but traditional carriers weren't built for this speed. We built Shepherd to solve that.

We announced our $42M Series B earlier this year! That brings our total funding to over $60M — led by Intact Private Capital, the investment arm of one of the largest insurers in the world. Intact is not only our lead investor but also a carrier partner, a testament to the confidence the incumbent industry has in what we're building.

We’re looking for product-minded, high ownership engineers to join our team! The Engineering team is HQ’d in SF, but we’re growing in NYC now too!

We’re hiring for 2 Senior Full Stack Software Engineers, 1 Machine Learning Engineer and 1 AI Product Manager in SF, and 2 Staff Full Stack Software Engineers in NYC. Engineers own projects end-to-end so full stack ability is expected.

Check out our open roles here: https://shepherdinsurance.com/careers Our stack includes: Typescript, React, Next.js, GraphQL w/ Apollo, Node.js, Postgres & Redis – If you have experience building AI agents or multi-step reasoning systems, we’d love to hear from you.

* In the form, be sure to mention that you heard about this opportunity via Hacker News. If you want to read more about our team and culture, check out our blog: https://shepherdinsurance.com/blog

PrairieLearn (Remote US) — Full-Stack Software Engineer — TypeScript / Postgres / React / AI

PrairieLearn (https://www.prairielearn.com) is an open-source assessment platform used by universities across the US (Berkeley, Princeton, Michigan, Illinois, and others). We power mastery-based learning and large-scale exams.

We’re a small, profitable, early-stage company (bootstrapped, no VC) that is growing quickly. Our users love us and we have very high retention and rapid spread through word of mouth. As an early-stage hire, you’ll work across the stack and enjoy meaningful ownership from day one.

Tech we use: Node.js / TypeScript backend, Postgres, AWS, React. We’re also developing AI tooling, including LLM agents to help instructors create content, and vision-language models to help grade student work. PrairieLearn is open core: https://github.com/PrairieLearn/PrairieLearn

Details:

- Location: Remote (US only)

- Salary: $100k-$180k depending on experience

- Benefits: Stock options (0.5% - 1.5%), unlimited PTO, flexible hours

- Role: Full-time. (We’re not able to sponsor visas at this time.)

Apply at https://www.prairielearn.com/jobs-ashby?utm_source=YeEJ5MAKk...