Location: Toronto, ON (Hybrid In Office Monday, Thursday and every second Tuesday)

BUILD SOMETHING YOUR NEIGHBOURS WILL LOVE

We’re building Toronto’s dedicated platform for home management to empower the city’s homeowners and to better connect our neighbours and the local Pros they trust.

Our focus is purely on the GTA market right now. We build our property base one street at a time, and our marketplaces one neighbourhood at a time. We’re a local tech company in every sense of the word. We start with integrity, neighbourhood values, and competitive craftsmanship, and we build our business on neighbourhood trust.

We believe in holistic solutions to consumer problems. We believe in high-trust hyperlocal communities. We believe in low commission marketplaces that the best Pros can actually say yes to. And we believe that tech companies should go to work for the locally loved Pros of the GTA rather than trying to get those Pros to effectively work for the tech company. We believe that it’s good business to care. We believe that this problem space deserves a form of digital transformation that the people and Pros of Toronto can trust and invest in.

If this resonates with you and you’re at a point in your career and your life where you want to do something uniquely difficult for a meaningful outcome, you’ve found your next home.

ROLE OVERVIEW

The engineering team is looking for an AI Engineer who can build the LLM and agentic capabilities that bring intelligence into the Quartermaster experience. This role is less about traditional ML modelling and more about the hands-on software engineering needed to get LLMs into production: prompting, agentic workflows, and API-based model integration, shipped through our existing Python/TypeScript stack.

This is a hands-on role for an ambitious engineer, someone with a strong SaaS software background who's looking to grow into owning intelligent features end-to-end. You don't need a modelling or academic ML background; you need solid engineering fundamentals, real experience shipping LLM-backed features, and the initiative to help figure out where intelligence belongs in the product next.

ROLE SALARY BAND

$150,000 - $190,000

TEAM VALUES

❤ Integrity – We prioritize integrity over comfort, convenience, and the short-cuts of success that drive metrics but undermine trust.

❤ Trust – We cannot win unless we win on trust. Trust is hard to earn and easy to lose. We need to be built for it in our DNA.

❤ Competitiveness – We believe that competitiveness is a critical complement to integrity and trust. If we’re not our customer’s best choice, then we’re wasting their time. We believe in the power of healthy competitive markets, and we believe we need to be uniquely competitive to win in this space. We have too much respect for the other players in this space to expect things to be easy. That’s a good thing.

❤ Empowerment – Any win we achieve needs to be first and foremost a win that we deliver to others, starting with our customers, and their long term best interests.

VACATION AND BENEFITS

We know the power it takes to be successful in a challenging mission and we want to ensure our team is rested and ready to go.

We offer 30 days of PTO annually, which can be used for vacation, personal days, or illness. Five of these days are designated as company-wide closures around the start and end of the year.
In addition, our benefits plan covers health, dental and wellness to add that extra pep in our step, and help us sleep at night.
We have a tech allowance benefit to help set you up for work.
We have pregnancy and parental leave policies, and we’re ready to support your family’s next stage of growth.

EMPLOYEE OWNERSHIP:

We’re a team on a mission. We expect a high degree of ownership from each other and we pair that with higher than usual employee ownership in the company.

Key Responsibilities

Design, build, and ship LLM-powered and agentic features across the Quartermaster product — maintenance guidance, contractor matching, document understanding, conversational experiences, and similar user-facing intelligence
Integrate LLM APIs and agentic frameworks into our Python/TypeScript SaaS stack, following our existing engineering patterns and conventions
Take ownership of these features from API design and prompt/agent design through testing, deployment, and monitoring in production
Collaborate with product and engineering to scope what to build next, not just execute a fixed spec
Apply sound software engineering practice (testing, code review, incremental delivery) to LLM-based features — including evaluating and regression-testing prompt and agent behavior, not just conventional code paths
Help establish internal patterns and conventions for building and maintaining LLM/agentic features as the team grows this capability

Required Qualifications

Hands-on experience building with LLMs — prompting, API integration, and/or agentic workflows (not limited to a research or notebook context)
Strong software engineering fundamentals, with hands-on experience in Python
Background in SaaS web development — building and shipping features in a production web application
Experience with agentic frameworks (e.g., LangChain, PydanticAI, LangGraph, or equivalent)
Experience deploying and operating production services in a cloud environment
Awareness of LLM API cost, latency, and rate-limit tradeoffs when designing production features
Comfortable working across the stack — from backend APIs to the LLM/agent layer
A product-engineering mindset: you care about shipping a feature that works for real users, not just a model that scores well offline

Preferred (Nice to Have)

Experience with a Python async web framework (FastAPI or similar) and a document database (MongoDB or similar)
Experience with Typescript
Experience with Claude Code or similar AI-assisted development tools
Experience with vector search / retrieval pipelines
Prior experience in a small-team or early-stage SaaS environment, owning features end-to-end

THIS IS A GOOD FIT FOR YOU IF…

You’re mission-driven and looking to solve the mission’s hardest problems.
You’re at a point in your life and your career where you want to tackle a uniquely demanding job to produce meaningful impact.
You’re keen to work in-person with a team on a set Monday, Thursday and every second Tuesday schedule.

LOCATION

Hybrid #LI-HYBRID