Senior Software Engineer - Applied AI

About Feathery

Feathery helps insurance and wealth management firms modernize how they collect and process data. Enterprise teams use our platform to run high-stakes workflows — from new client onboarding and underwriting to automated account openings — with speed and precision.

We're growing fast, and as enterprise demand scales, so does our engineering team.

Why We're Hiring

AI is no longer a side feature at Feathery — it's core to how we build. From a conversational workflow builder that generates complex forms and logic on your behalf, to intelligent document extraction and multi-model orchestration, we're making the product smarter at every layer.

To keep pace with that ambition, we're looking for a Full Stack Engineer to join the AI team and own these capabilities end-to-end.

About the Role

You'll be a high-ownership contributor who works across the entire stack — designing LLM-powered backend services, building streaming APIs, and crafting the frontend experiences that bring everything together. This role touches TypeScript services, Python APIs, React interfaces, and cloud infrastructure.

You'll need to zoom out for system architecture and zoom in to ship polished, production-ready features.

What You'll Do

AI Product Development

• Ship end-to-end AI features spanning backend services through to user-facing UI
• Architect and build LLM agent systems — tool use, planning, and multi-step execution
• Design streaming APIs (SSE) that power real-time, conversational product experiences
• Own features from initial concept through production, iterating closely with users

Backend Systems & AI Infrastructure

• Build and scale TypeScript and Python services for AI orchestration and document processing
• Work with multiple LLM providers (Claude, GPT, and others), balancing cost, latency, and quality
• Develop async pipelines on AWS (Lambda, SQS, S3, Textract)
• Design the APIs and data models that connect AI capabilities to the broader platform

Frontend Experience

• Build responsive, interactive UIs in React and TypeScript
• Implement real-time streaming interfaces for conversational AI features
• Partner with design to deliver polished, accessible experiences
• Contribute to frontend architecture and state management decisions

Cross-Functional Collaboration

• Work with product and design to shape the AI feature roadmap
• Partner with the core platform team on APIs, data models, and SDK surfaces
• Contribute to decisions around agent design, prompt engineering, and system reliability
• Translate real customer workflows into AI-powered solutions

About You

• 3–6+ years building full stack applications
• Strong TypeScript/JavaScript skills with hands-on React experience
• Backend experience in Node.js/Express, Python/Django, or equivalent
• Genuine curiosity about AI/LLM technology and what it can unlock in products
• Experience designing APIs, including streaming and event-driven patterns
• Familiarity with AWS or cloud infrastructure
• Comfortable shipping iteratively in a fast-moving, high-growth environment
• Clear communicator and strong team collaborator

Bonus

• Hands-on experience with LLM APIs (Claude, GPT, etc.) — tool use, prompt engineering, or agent design
• Background in document processing, OCR, or data extraction
• Experience with streaming protocols (SSE, WebSockets) and real-time UI
• Familiarity with multi-model orchestration or AI pipeline design
• History optimizing for high throughput and low latency
• Experience in financial services or other regulated industries
• Background in high-growth B2B SaaS

What We Offer

• Competitive salary and equity
• Health, dental, and vision coverage
• Unlimited PTO
• Downtown Toronto office
• Daily office snacks and team lunches
• A low-ego, supportive team that values ownership and growth
• Annual company offsite

If you're excited about building AI experiences that power critical workflows — and want real impact at a fast-growing startup — we'd love to hear from you.

Feathery is an equal opportunity employer committed to building an inclusive team. We do not discriminate on any legally protected basis and provide reasonable accommodations upon request.