Tailwind
Frontend Product Engineer
Toronto
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hirly's read of this role
- Seniority
- Mid level
- Country
- CA
- Work mode
- Remote-friendly
- First seen by hirly
- 2 Sept 2026
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the posting
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 Frontend Product Engineer , you’ll be building the core user-facing product experience at Tailwind. This role is perfect for someone who cares deeply about usability, aesthetics, and performance — the craftsperson who wants to ship delightful, reliable software at a rapid pace.
You’ll work directly with the CTO, product managers, and designers to define, build, and polish features that brokers use daily to run their businesses. Every pixel and interaction you create will directly impact how insurance gets done across thousands of workflows each week.
What You’ll Do
Own the frontend experience for key product areas: from design handoff to production.
Build high-performance, elegant UIs in React JS/TS and Tailwind CSS with an obsession for user experience and polish.
Collaborate with backend engineers on full-stack features, ensuring seamless API integration and data flow.
Work closely with Product & Design to translate user pain points into intuitive, delightful experiences.
Contribute to design systems and frontend best practices as we scale the engineering team.
Ship fast: our CI/CD pipeline takes from merge to production — every engineer deploys on day one.
What Makes You a Great Fit
2+ years of frontend experience building and shipping production web apps.
Strong in React and modern JS/TS frameworks; exposure to design systems is a plus.
Eye for visual design, user interaction, and performance optimization .
Startup-ready: you thrive in ambiguity, enjoy wearing multiple hats, and bias toward action.
Bonus: experience with AI-driven products or interest in agentic AI/RPA workflows.
Why You Should Work Here
Impact: Every feature you build transforms how brokers run their business.
Speed: We ship fast, with minimal red tape and direct access to founders
Growth: Early role = huge career upside as we scale engineering and product.
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.
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