Founding Engineer

Ultrassure; Toronto; On-site; CAD 110,000 - 170,000; Full time

Benefits offered by this job

Gym membership

Equity

Job summary

Ultrassure, located in downtown Toronto, is building an AI-driven system for commercial insurance. We seek a full-stack software engineer to help shape core product and AI systems as an early team member.

You will work closely with the CTO and customers to take problems from conversation to architecture to production, shipping high-impact solutions quickly. You will own end-to-end features across frontend, backend, infrastructure and applied AI, interacting directly with customers to refine

Qualifications

• Strong software engineering fundamentals.
• Experience with TypeScript and modern React or Next.js applications.
• Experience building backend applications and APIs.
• Experience working with production cloud infrastructure, ideally AWS.
• Experience building real applications with LLMs rather than simply calling a model API.
• Strong product judgment and an instinct for simple solutions.
• A bias toward shipping and iterating with users.
• High ownership and comfort operating with limited direction.
• Good instincts around security, reliability and production systems.
• Curiosity about difficult workflows, messy documents and unstructured data.
• The ability to work from our office at Bay & King in downtown Toronto.

Responsibilities

• Build and ship product using Next.js, TypeScript, Python, Django and AWS.
• Design features end-to-end, from database models and APIs to frontend UX.
• Build production AI workflows using OpenAI, Anthropic and other leading models.
• Work with agents, tools, MCP, structured outputs, retrieval systems and evals.
• Use Codex and other AI development tools extensively as part of your daily workflow.
• Build systems for document parsing, clause extraction, data enrichment, comparison and workflow automation.
• Turn complex insurance documents and workflows into simple, reliable software.
• Improve authentication, RBAC, multi-tenancy, queues, caching and secure data pipelines.
• Build and maintain production infrastructure on AWS.
• Improve testing, observability, monitoring, CI/CD, security and release quality.
• Work directly with customers to understand messy real-world workflows and rapidly turn those problems into product.

Skills

TypeScript

React/Next.js

Backend development

AWS

LLMs

Product sense

Ownership

Tools

OpenAI

Anthropic

Job description

Ultrassure is building the AI system of work for commercial insurance.

Insurance is a roughly $7.5 trillion global industry, but much of it still runs on PDFs, spreadsheets, email and legacy software. We build AI-native software that helps insurers, reinsurers, MGAs and brokers turn complex, unstructured insurance data into structured information, automated workflows and better decisions.

Our platform is used by insurance organizations across Canada, the United States, the United Kingdom, Bermuda and the Cayman Islands. More than $10 billion of premium already flows through the platform.

We grew from zero to six-figure ARR, are growing quickly and are now at the seed stage.

We are a small, focused team in downtown Toronto. We ship every day, work closely with our customers and care more about building useful software than process for the sake of process.

The Role

We are looking for a Full-Stack Software Engineer to join Ultrassure as one of our early engineers.

You will work closely with our CTO, leadership team and customers to build the core product and AI systems behind Ultrassure.

This is a high-ownership role. You will take problems from customer conversation to architecture to implementation to production. You will have a meaningful influence on what we build, how we build it and the engineering culture we create as the company grows.

This is not a "wait for the next sprint" environment. We talk to customers constantly, identify valuable problems and ship solutions quickly.

If you like owning meaningful problems, moving fast and seeing your work used by real customers shortly after you build it, you will probably enjoy working here.

What You Will Do

You will work across frontend, backend, infrastructure and applied AI.

You will:

• Build and ship product using Next.js, TypeScript, Python, Django and AWS
• Design features end-to-end, from database models and APIs to frontend UX
• Build production AI workflows using OpenAI, Anthropic and other leading models
• Work with agents, tools, MCP, structured outputs, retrieval systems and evals
• Use Codex and other AI development tools extensively as part of your daily workflow
• Build systems for document parsing, clause extraction, data enrichment, comparison and workflow automation
• Turn complex insurance documents and workflows into simple, reliable software
• Improve authentication, RBAC, multi-tenancy, queues, caching and secure data pipelines
• Build and maintain production infrastructure on AWS
• Improve testing, observability, monitoring, CI/CD, security and release quality
• Work directly with customers to understand messy real-world workflows and rapidly turn those problems into product

You will not be limited to one part of the stack. If something important needs to be built, you should be comfortable figuring it out and owning it.

What We Are Looking For

We care much more about what you can build than how many years you have been working.

You should have:

• Strong software engineering fundamentals
• Experience with TypeScript and modern React or Next.js applications
• Experience building backend applications and APIs
• Experience working with production cloud infrastructure, ideally AWS
• Experience building real applications with LLMs rather than simply calling a model API
• Strong product judgment and an instinct for simple solutions
• A bias toward shipping and iterating with users
• High ownership and comfort operating with limited direction
• Good instincts around security, reliability and production systems
• Curiosity about difficult workflows, messy documents and unstructured data
• The ability to work from our office at Bay & King in downtown Toronto
• Legal eligibility to work in Canada

You do not need a specific number of years of experience.

You might be an exceptional new graduate who has built a lot outside of school. You might have several years of experience shipping production software. We care most about engineering ability, product taste, speed, curiosity and evidence that you build things.

Bonus Points

We would be particularly interested if you have experience with:

• Insurance, fintech, B2B SaaS or other regulated industries
• Document parsing, OCR or extraction pipelines
• LLM evals and production AI systems
• Agents, MCP servers or tool-using AI systems
• Retrieval, embeddings or vector databases
• Complex authorization or permissions systems
• Multi-tenant B2B software
• AWS infrastructure at meaningful production scale
• Open-source projects, side projects or products you built yourself

None of these are requirements.

Why Ultrassure

Real customers, real usage

You will be building software used in production by insurance organizations across Canada, the United States, the United Kingdom, Bermuda and the Cayman Islands, with more than $10 billion of premium already flowing through the platform.

A massive market undergoing a major technology shift

Commercial insurance is one of the world's largest industries and many of its most important workflows still revolve around documents, spreadsheets and email. AI makes it possible to redesign how much of this work gets done.

Build at the application layer of AI

We are not building another generic chatbot. You will work on difficult problems involving long and complex documents, structured extraction, agentic workflows, evidence, permissions, reliability and high-stakes business processes.

Join at the seed stage

The product is live, customers are paying and usage is growing, but the team is still small enough that an individual engineer can have an outsized impact on the product, architecture and company.

Meaningful ownership

You will have significant influence over product decisions, technical architecture and engineering standards as the engineering team grows.

Work directly with customers

Our engineers are close to the people using what we build. You will see the problems firsthand, ship solutions and get feedback quickly.

We ship continuously and regularly turn customer feedback into production features within days rather than quarters.

Meaningful equity

Competitive compensation plus meaningful equity in a seed-stage company.

Downtown Toronto

We work together from our office at Bay & King. Gym and squash memberships are included.