Senior Software Engineer - Applied AI

About Feathery

Feathery automates data intake workflows for insurance and wealth management firms. Industry leaders rely on Feathery to power mission-critical workflows like underwriting, client onboarding, and automated account openings.

With rapid revenue growth and expanding enterprise demand, we’re scaling our engineering team to support increasingly complex, data-intensive workflows across our platform.

Why We’re Hiring

Feathery is building an AI-native product experience — from a conversational workflow builder that creates complex forms and logic on behalf of users, to intelligent document extraction and multi-LLM orchestration.

As our AI capabilities become central to the product, we're hiring a Full Stack Engineer to join the AI team and build these features end-to-end — from designing LLM-powered services and streaming APIs to crafting the interactive UI that brings them to life.

About the Role

This is a high-ownership role on the AI team which blends:

Working across the full stack to ship AI-powered product features

Building systems that orchestrate LLM agents, process documents, and generate workflows

Owning the frontend experiences that make them intuitive

Working across TypeScript services, Python APIs, React interfaces, and cloud infrastructure

You’ll zoom out to understand system architecture and zoom in to deliver polished, end-to-end product experiences.

What You’ll Do

AI Product Development

Build end-to-end AI features from backend services through to frontend UI

Design and implement LLM agent systems including tool use, planning, and multi-step execution

Develop streaming APIs (SSE) that power real-time conversational interfaces

Own features from concept through production, iterating based on user feedback

Backend Systems & AI Infrastructure

Build and scale TypeScript and Python services for AI orchestration and document processing

Work with multiple LLM providers (Claude, GPT, etc.) and optimize for cost, latency, and quality

Develop asynchronous pipelines using AWS services (Lambda, SQS, S3, Textract)

Design APIs and data models that connect AI capabilities to the core platform

Frontend Experience

Build responsive, interactive UIs using React and TypeScript

Implement real-time streaming interfaces for conversational AI features

Collaborate with design to create polished, accessible experiences

Contribute to frontend architecture and state management patterns

Cross-Functional Collaboration

Partner with product and design to define AI feature roadmaps

Integrate with the core platform team on APIs, data models, and SDK surfaces

Contribute to architectural decisions around agent design, prompt engineering, and system reliability

Translate customer workflows into AI-powered solutions

About You

3–6+ years of experience building full stack applications

Strong TypeScript/JavaScript proficiency with React experience

Backend experience with Node.js/Express, Python/Django, or similar

Genuine interest in AI/LLM technology and building AI-powered products

API design experience, including streaming and event-driven patterns

AWS or cloud infrastructure familiarity

Comfort shipping iteratively in a fast-paced, high-growth startup

Strong communication and collaboration skills

Bonus

Hands-on experience building with LLM APIs (Claude, GPT, etc.) — tool use, prompt engineering, or agent architectures

Document processing, OCR, or data extraction experience

Experience with streaming protocols (SSE, WebSockets) and real-time UIs

Familiarity with multi-model orchestration or AI pipeline design

High throughput and low latency optimization background

Financial services or regulated industry experience

High-growth B2B SaaS company background

What We Offer

Competitive compensation and equity

Health, dental, and vision coverage

Unlimited PTO

Downtown Toronto office location

Office snacks and lunches

A supportive, low-ego team that values ownership and growth

Company offsite to connect and recharge

If you’re excited about building AI product experiences that power critical workflows — and want to have a meaningful impact at a fast-growing startup — we’d love to meet you.

Feathery is an equal opportunity employer and does not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or any other legally protected characteristic. We’re committed to building an inclusive team and provide reasonable accommodations upon request.