AI Automation Engineer

Osmow's | Digital & Technology Team

Reports to: Director of Digital

Location: Hybrid, GTA

Type: Full-time, permanent

Build the AI platform behind a leading QSR brand

Osmow's is one of Canada's fastest-growing restaurant brands, with over 250 locations across Canada and the United States. We are building technology to support our continued growth.

Our Digital & Technology team operates more like a focused product team than a traditional restaurant IT department. We build, automate, experiment quickly and scale what works across hundreds of restaurants.

Our approach is simple: Automate Improvement. We identify areas where data, AI and automation can remove friction, accelerate decision-making and improve how the business operates at scale.

We are building an internal data, AI and automation platform to improve reporting, streamline repetitive work and support business decisions across the organization.

Our phased roadmap includes tools supporting Operations, district managers, Finance, Marketing, training and franchisees. Projects may include workflow automation, accessible business insights, franchisee assistance and learning management capabilities, based on business priorities.

That's where you come in.

Working directly with the Director of Digital, you will maintain and expand our data, AI and automation capabilities. Your initial priorities will be keeping existing data pipelines and APIs reliable, connecting new business systems, and developing practical automation and platform functionality. The Director will define business priorities and desired outcomes, review code and approve production deployments, while you independently develop, troubleshoot and maintain the solutions. The Director will also provide backup coverage during absences.

What you'll build

Production-grade Python data pipelines and services connecting restaurant data, third-party APIs, business systems and databases.
AI workflows and agents using LLM APIs and appropriate development frameworks.
Practical web applications and interfaces that make business information easier for employees and franchisees to understand and use.
Tools and integrations that help teams access information and act on business needs.
Automation for reporting, restaurant onboarding, ownership transfers and operational handoffs.
Monitoring, reconciliation, testing and appropriate controls to support reliable, auditable data and AI-assisted workflows.
Internal platforms and services designed to scale across hundreds of locations and multiple business functions.

What you'll do

Develop and deploy software services and web applications using Git, code review and production deployment approval from the Director of Digital.
Build, prompt, test and evaluate LLM-powered workflows and agents.
Design SQL tables and views that support trusted operational and financial reporting.
Validate and reconcile new data sources with Finance before they are used in production reporting.
Integrate REST APIs, webhooks, OAuth flows and third-party platforms, including the ones with no clean documentation.
Turn repetitive manual processes into reliable, scalable automation, proving each in a dry run first.
Own ongoing monitoring, data accuracy and troubleshooting for existing pipelines, APIs and integrations, including updates for restaurant openings, ownership transfers and changes to connected systems.
Work with Finance, Marketing, Operations, training teams and senior leadership to clarify requirements and identify practical improvements.
Document solutions, dependencies, monitoring and recovery procedures so the team can support, maintain and extend them.

We work in short, practical phases with clear go/no-go gates. We would rather ship something small, validated and useful than spend months designing the perfect architecture.

What we're looking for

Must have

2 to 6 years of experience building production software, automation or data pipelines, with Python as your primary language and demonstrated ability to develop and maintain reliable solutions independently.
Strong Postgres and SQL skills: you can write views, reason about keys and duplicates, and explain why two totals differ.
Hands-on experience shipping something with an LLM API such as Anthropic, OpenAI or similar that people actually use.
Understanding of prompts, evaluations, failure modes, latency and API cost.
Experience with REST APIs, webhooks, OAuth and third-party integrations.
Practical Linux and cloud knowledge, including logs, secrets and deployments.
Git as part of your normal workflow.
Strong written communication and documentation skills, with the ability to clarify incomplete requirements, identify dependencies and recommend practical solutions in collaboration with business stakeholders.

Nice to have

Claude Code, MCP or agent frameworks such as Pydantic AI or LangGraph.
Supabase and AWS experience.
Observability for pipelines and agents: dead-man checks (Healthchecks.io or similar), structured logging, and alerting that catches silent failures.
Restaurant, retail or franchise technology experience.
Experience working with high-volume operational or transactional data.
js on Vercel, including streaming AI responses into the UI (Vercel AI SDK or similar).
Experience working with Finance teams where numbers must reconcile.

This role may not be the right fit if

You want to work exclusively in no-code tools.
You are looking primarily for AI research or model-training work.
You prefer a large engineering organization with multiple layers between engineering and the business.
You are uncomfortable owning a problem from investigation through deployment.

Compensation and benefits

Base salary: $95,000 to $125,000 CAD, based on experience and demonstrated production AI/LLM work.

You'll also receive:

Company laptop and the tools required to do the job.
AI development tools, API budgets and cloud access.
Relevant professional development may be supported, subject to Company policy, budget and prior approval.

Location

This is a hybrid role based in the GTA, with 3 days per week at the Osmow's head office in Mississauga and regular remote work.

Occasional restaurant visits are part of the role because some of the best technology decisions come from seeing how the business operates.

Why this role and why Osmow's

Osmow's started as a single restaurant and has grown into a major North American franchise brand. That entrepreneurial mindset still shapes how we work: we move quickly, challenge old processes and build technology ourselves when the right solution does not already exist.

We already use AI and automation in our business. Your work will support practical improvements for employees and franchisees, with deployment based on testing and business priorities.

You'll have direct access to the business, the data and the people making decisions, with very few layers between identifying an opportunity and building the solution. You'll also help define what ‘Automating Improvement’ means in practice.

You will help improve an evolving platform with real users and business needs. If you enjoy building and maintaining practical software, data and automation solutions, we'd like to hear from you.

How to apply

Apply through this posting with:

A resume or LinkedIn profile.

An optional portfolio or link to a relevant software, data or AI project, with a brief description of your contribution.

Shortlisted candidates will be invited to an initial interview and a practical technical assessment. Assessment instructions and the expected time commitment will be provided at that stage.

We thank all applicants for their interest; however, only those selected for an interview will be contacted due to the high volume of applications. No phone calls or agencies please.

We are committed to providing an inclusive and accessible recruitment process in accordance with the Accessibility for Ontarians with Disabilities Act (AODA) and applicable employment legislation, including fair hiring and transparent recruitment practices. Accommodation is available upon request throughout the recruitment process.