Founding Engineer

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 RoleWe 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 DoYou 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 ForWe 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 PointsWe 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 UltrassureReal customers, real usageYou 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 shiftCommercial 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 AIWe 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 stageThe 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 ownershipYou will have significant influence over product decisions, technical architecture and engineering standards as the engineering team grows.
Work directly with customersOur 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 equityCompetitive compensation plus meaningful equity in a seed-stage company.
Downtown TorontoWe work together from our office at Bay & King. Gym and squash memberships are included.
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