Technical Lead, Founding Engineer

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

This role is remote to start, based in the United States, with the potential to become a hybrid position (Austin, NYC, Nashville, and Atlanta under consideration)

Why SafeStay?
The problem: Short-term rental managers run real businesses on coverage designed for other industries. Nobody has built this properly, so we are.
The stage: We are early. The platform, the products and the way we work are all still being decided, and the person doing the work is usually the person making the call.
The team: A small group of insurance operators and builders who move fast and hold a high bar. High standards, low ego.
The offer: Competitive pay, equity, and benefits.