Full Stack Engineer

Department: Engineering

Location: Toronto, San Francisco

Employment Type: FullTime

About Tailwind

Tailwind is organizing the world's insurance information.

Insurance is one of the largest markets in the world, and it runs entirely on PDFs and antiquated infrastructure. We like it that way. While the industry takes years to roll out change, we ship in days.

Tailwind is backed by the earliest investors in financial infrastructure and technology titans Ramp ($23B), Robinhood ($100B) and Cognition ($10B), as well as over a dozen founders and leaders of billion dollar+ companies (including Segment, Newfront, Qualtrics, Cursor, etc) and even NBA champions.

About the Role

As a Full Stack Engineer, you’ll work across Tailwind’s core application and backend systems, shipping features that directly power our insurance automation platform.

This role is perfect for someone who enjoys working end-to-end — from APIs to UI — and wants to build in a fast-moving, high-impact startup environment.

What You’ll Do

• Design and implement backend services in Java / Spring Boot for insurance automation workflows.

• Build full-stack features spanning APIs, backend logic, and frontend UI (React).

• Collaborate with AI engineers to integrate LLM-powered extraction and automation pipelines.

• Work closely with product & design on user-facing features for brokers and carriers.

• Help scale our workflow orchestration system (50+ customers × 1M+ annual workflows).

• Contribute to engineering best practices, architecture decisions, and code reviews.

What Makes You a Great Fit

• 2+ years of experience building full-stack or backend-heavy applications.

• Proficiency in Java or interest in learning it quickly (Spring Boot experience a plus).

• Experience with React or similar frontend frameworks.

• Comfort working with APIs, orchestration systems, or data pipelines.

• Startup mindset: bias toward shipping, iteration, and learning fast.

Why You Should Work Here

• Impact: Every feature you ship transforms how brokers handle renewals.

• Speed: Ship to production daily in a <5 min CI/CD pipeline.

• Career growth: Early role = huge upside as we scale engineering and product orgs.

• Hybrid culture: High-collaboration office time balanced with focus days.

• Elite Team: Our core team has worked together 3 times now, hailing from Carta ($7B) and AppDirect ($2B) and includes veterans from Ramp, Apple, Salesforce and C3 AI - people who know what great product looks like, and what it takes to build it fast.

Tailwind is backed by the earliest investors in financial infrastructure and technology titans Ramp ($23B), Robinhood ($100B) and Cognition ($10B), as well as over a dozen founders and leaders of billion dollar+ companies (including Segment, Newfront, Qualtrics, Cursor, etc) and even NBA champions.