About Tailshift:

Jargon alert! We’ve tried to make this simple, but if any of it doesn’t make sense, don’t stress. We’ll happily answer questions about the company at any stage of the process.

Tailshift is an AI-native startup building the intelligence layer for the insurance industry. Insurance is one of the biggest markets in the world, but most of its data is messy and stuck in PDFs, spreadsheets, and outdated systems. This makes it hard for companies to understand risk (what could go wrong), price it fairly, and share that risk with other insurers (through reinsurance, where insurers transfer part of their risk to other companies so no one carries the full cost of a very large loss).

We focus on casualty insurance (covering car accidents, workplace injuries, or lawsuits — risks tied to people and businesses). The data here comes from claims (records of accidents or losses), bordereaux (industry spreadsheets that track thousands of policies at once), and underwriting files (information insurers use when deciding whether to cover someone).

Our AI-powered tools help the market:

• Parse messy data so companies can price risk more confidently
• Spot hidden drivers of reserve deterioration (when insurers set aside money to pay claims, but it turns out not to be enough)
• Enable new types of reinsurance transactions (risk-sharing deals between insurers that weren’t possible before)

As we expand across reinsurers, brokers (middlemen who connect buyers and sellers of insurance), and cedants (insurance companies that pass risk to reinsurers), we’re wiring together a federated learning system (a way for companies to learn from data collectively without sharing sensitive raw data). The end goal: making casualty portfolios transparent, comparable, and ultimately tradable.

We’re already market leaders in specialty casualty and we’re just getting started.

About the team:

You’ll be surrounded by people who love markets, data, and technology — and who are eager to mentor and share what they’ve learned.

Our team has:

• earned PhDs at Stanford,
• built scalable investment strategies at Citadel and DE Shaw,
• created federated learning software for genetics labs,
• and developed financial infrastructure at Mercado Libre

We’re a well-funded startup, founded in 2022 and backed by Lightspeed Venture Partners, Munich Re Ventures along with other fintech VC funds and insurance angels — so we’re not going anywhere.

Why this matters for you: you get the rare chance to learn directly from people who’ve solved some of the hardest problems at world-class institutions, but in a small startup where your work will have an immediate impact.

About the role: