Senior Software Engineer - Applied AI

About Feathery

Feathery is the AI operating system for financial institutions. With hundreds of clients and over $30 million raised, Feathery is the fast-growing leader in financial agentic automation. Industry leaders like Tokio Marine, Sequoia Financial, and Cerity Partners run their client-facing workflows on Feathery, from onboarding and risk assessment to reconciling systems and generating proposals and reports.

At the center of it all is Robin, our AI operations assistant. Robin scans client documents, configures and deploys workflows, assists users in their day-to-day work, takes notes during meetings, and supports a growing range of operational tasks across the client lifecycle.

We're building a future where financial operations shift from paperwork, manual data entry, and disconnected systems to intelligent, automated workflows that let firms spend their time on clients instead of process. We're proud to be backed by world-class investors who share that vision, including Portage Ventures, Allstate Ventures, and Index Ventures, among others.

We're driven by a shared commitment to excellence and velocity. Our values — Own the Problem, Grit Beats Gloss, Say It Straight — shape how we work and grow as a team.

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.