Careers

Build an insurance company from zero

SafeStay is building an insurance company for the short-term rental industry, from the ground up. This is the first engineering hire, which means the platform gets built from nothing by whoever takes the job.

Remote to start, United States · Full-time · First engineering hire
Why this one

Early enough that every decision is still yours to make

Most people never get to build the whole thing. This one gets built now, from nothing, by a very small number of people, and the person who takes this role sets the technical direction for all of it.

A real business, not an experiment

This is not a side project or a prototype. The company exists and the platform you build will carry the business itself from the day it goes live.

The technical direction is open

There is no legacy stack to inherit and no committee to convince. The first engineer decides what gets built, what gets bought, and what waits.

Insurance is a real engineering problem

Quoting, binding, billing, reconciliation, claims, regulatory reporting. Correctness matters, the domain has rules, and getting the details right is the craft.

Open roles

One role, open now

If it fits, apply. If it nearly fits, apply anyway and tell us why.

Technical Lead, Founding Engineer

Full-time Remote to start · United States Engineering · first hire

You will build the platform this company runs on: the system of record and billing, and the claims tooling the team works in. As a player-coach you will be equally comfortable in the architecture diagrams and in the codebase, and you will hire and lead the engineers who follow you.

About SafeStay

SafeStay is building an insurance company for the short-term rental industry. It is a category the insurance market has never served properly, so the people running these businesses have made do with products built for other industries and stitched together from more than one provider. We are building for this industry from the ground up rather than adapting to it.

About the role

We are hiring a founding Engineering Manager and Technical Lead to build this from the ground up. This is a rare 0-to-1 opportunity: you will help shape the technical vision, stand up the platform, and hire and lead the engineering team that brings it to life.

As a player-coach, you will be equally comfortable in the architecture diagrams and in the codebase. You will own the systems that ingest partner activity, serve as the billing source of truth, and power claims handling for our partners and operators. The decisions you make in the first year will define how this business scales for years to come.

What you will own

1
System of record and billing

The financial backbone of the business. You will build the systems that ingest partner activity and serve as the authoritative billing source of truth, and turn that activity into accurate monthly invoices.

2
Internal claims portal

The internal system that makes claim handling efficient and compliant. You will build the tooling our team relies on to track, adjust and resolve claims with a clean audit trail.

What you will do

  • Build the team. Hire, onboard and lead a high-performing team of engineers, and set the bar for talent, culture and technical excellence.
  • Set technical direction. Own architecture and technical strategy across ingestion, the system of record, reconciliation and invoicing, and the claims portal.
  • Ship as a player-coach. Stay hands-on in the codebase, especially in the early months, while growing the team's ability to deliver without you in the critical path.
  • Guard data integrity. Treat billing and claims data with the rigor of a financial system. Correctness, auditability and reconciliation are non-negotiable.
  • Partner cross-functionally. Work closely with product, operations, finance and partner-facing teams to translate business needs into reliable systems.
  • Establish the foundations. Set engineering practices, on-call, quality standards, and the roadmap for a durable, scalable platform.

What we are looking for

  • Seven or more years of full-stack software engineering experience.
  • Two or more years managing or formally leading engineering teams.
  • A track record of building and scaling backend systems and APIs, ideally financial, billing or transactional systems where correctness matters.
  • Experience integrating with third-party partner systems and building bi-directional sync.
  • Experience in modern tech stacks and architectures.
  • An AI-forward engineering leader: a technical leader who builds with AI daily.
  • Proven ability to hire, grow and lead engineering teams, with a genuine appetite for both leadership and code.
  • Strong data modeling instincts and comfort with reconciliation, audit trails and systems of record.
  • Excellent communication and cross-functional partnership skills.

Great to have

  • Experience taking a product, platform or a new business line from 0 to 1.
  • Experience in the insurance or fintech spaces.
  • Familiarity with billing, invoicing or reconciliation platforms.
  • Background operating in an early-stage or new-business-line environment inside a larger company.

Location and how to apply

This role is remote to start, based in the United States, with the potential to become a hybrid position. Apply through our application page, where you can upload your CV directly. It goes to the hiring manager, not to a queue, and you will hear back either way.

SafeStay is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Apply

Technical Lead, Founding Engineer

Every application is read by the hiring manager, not a queue, and you will hear back either way.

Applications are handled through our hiring system. It takes a few minutes, and you can upload your CV directly.

Apply on our application page

Want to see every open role? View all openings. SafeStay is an equal opportunity employer.