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Added 23 mins ago
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Principal – Municipal Engineering
WalterFedy
Kitchener, ON
- Full-time
Lead high-profile projects from conception through completion, ensuring that all design elements align with client goals and project objectives.
Added 1 hour ago
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ModiFace - DevOps Developer
L'Oréal
Toronto, ON
- Full-time
Work directly with the application development team’s tech lead and/or product owner to prioritization of infrastructure and DevOps tasks to meet the team’s business roadmap
Added 1 hour ago
SC
Wet Utilities Engineer (P.Eng)
SYSTRA Canada
Toronto, ON
- Full-time
Seeking an experienced Wet Utility Engineer for a new LRT Project. The role focuses on water, storm, and sanitary infrastructure, including water main relocation and sizing, drainage…
Added 1 hour ago
Program Director
Lightworks
Toronto, ON
Lead delivery governance across complex AI, cloud, and modernization programs, ensuring milestones, dependencies, risks, decisions, and outcomes are clear across all workstreams
Added 1 hour ago
CG
Software Engineer III - Financial Services
Cover Genius
Vancouver, BC
- $115,000 to $145,000 CAD / year
- Full-time
As a Software Engineer 3 in the Financial Services and Merchants domain, you will design, build, and maintain solutions for our top-tier partners across multiple platforms. Each partner…
Added 1 hour ago
FT
Senior Workday Functional Specialist
Fanshawe Toronto@ILAC
London, ON
- Full-time
…implementation of Workday, a modern cloud-based enterprise platform that is reshaping how we support our employees, finances, and future student services. Having successfully deployed…
Added 3 hours ago
Development Lead - Air Canada Mobile Application
Air Canada
Toronto, ON
As the most senior engineer on the mobile application, the Development Lead is both the design authority for the mobile platform and the primary delivery authority within Air Canada’s…
Added 3 hours ago
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Principal Full-Stack Developer - Platform & Infrastructure
MaintainX (An Autodesk Company)
Remote, Canada
- $131,000 to $230,000 CAD / year
- Full-time
- Remote
MaintainX is a leading mobile-first work execution platform for industrial and frontline teams. More than 13,000 customers, including Duracell, McDonald's, Shell, DHL and Volvo, use…
Added 3 hours ago
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Principal Full-Stack Developer - Platform & Infrastructure
MaintainX
Montreal, QC
- $131,000 to $230,000 CAD / year
- Full-time
MaintainX is a leading mobile-first work execution platform for industrial and frontline teams. More than 13,000 customers, including Duracell, McDonald's, Shell, DHL and Volvo, use…
Added 3 hours ago
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Principal Full-Stack Developer - Platform & Infrastructure
MaintainX
Toronto, ON
- $131,000 to $230,000 CAD / year
- Full-time
MaintainX is a leading mobile-first work execution platform for industrial and frontline teams. More than 13,000 customers, including Duracell, McDonald's, Shell, DHL and Volvo, use…
Added 3 hours ago
XC
Senior Developer Engineer/Leader - Montreal
Xcelerated Consulting Group, LLC.
Montreal, QC
- Contract
…regulatory obligations with precision, efficiency, and security. The platform serves as a centralized engine for data capture, validation, transformation, and reporting, integrating…
Added 3 hours ago
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Controls and Automation Engineer
Saltworks Technologies
Richmond, BC
- $90,000 to $120,000 CAD / year
- Full-time
Saltworks is a 2025 Technology Fast 50 company and EY Entrepreneur of the Year award winner. We lead our industry in adopting and developing AI across our products, projects, and…
Added 3 hours ago
MS
Consultant Conversion - Director, Infra Prod Mgmt & RE III
Morgan Stanley
Montreal, QC
- Full-time
Site Reliability Engineer, Logging Squad SRE Lead Organization: Observability
Added 3 hours ago
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Data Platform Engineer
Shift4
Toronto, ON
- Full-time
Shift4 is seeking a Data Platform Engineer to join our Data Platform team and build, maintain, and optimize the pipelines that move data from our production systems into our analytics…
Added 4 hours ago
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Manufacturing Engineer I
VitalBio
Oakville, ON
- Full-time
Lead comprehensive validation activities including planning and execution of validation protocols for equipment, facilities, and processes;
Added 4 hours ago
P
Senior Security Engineer - Cloud Security
PagerDuty
Toronto, ON
- Full-time
Senior Security Engineer - Cloud Security (Platform Engineering, Kubernetes & Identity)
Added 4 hours ago
H
Senior Application Security Engineer
Hays
Toronto, ON
- Contract
We are seeking a Senior Application Security Engineer / Snyk Migration Lead to join a critical application security initiative.
Added 4 hours ago
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Senior AI Machine Learning Engineer
SAP
Montreal, QC
- Full-time
We are hiring a Senior Machine Learning Engineer Scientist to lead the development of scalable graph-based and transformer-based modeling systems, along with production-grade ML pipelines.…
Added 5 hours ago
AC
Development Lead - Air Canada Mobile Application
Air Canada
Toronto, ON
- Full-time
As the most senior engineer on the mobile application, the Development Lead is both the design authority for the mobile platform and the primary delivery authority within Air Canada’s…
Added 5 hours ago
SC
Design Manager
SYSTRA Canada
Toronto, ON
- $120,000 to $160,000 CAD / year
- Full-time
The team will work closely with the Design Lead/Manager and other team members to ensure the successful execution of the projects. Their responsibilities include developing project plans,…
Added 5 hours ago
SC
Systems Safety Engineer
SYSTRA Canada
Toronto, ON
- Full-time
The Systems Safety Specialist will lead and support safety and assurance activities from concept through design, verification, validation, operation, and change management. The role…
Added 5 hours ago
SC
Senior Project Manager – Conventional Signaling
SYSTRA Canada
Toronto, ON
- $170,000 to $220,000 CAD / year
- Full-time
Lead the end-to-end delivery of conventional rail signaling projects, ensuring scope, schedule, budget, and quality objectives are achieved.
Added 5 hours ago
SC
Utilities Engineer – Interface Management (Senior)
SYSTRA Canada
Toronto, ON
- Full-time
The Utilities Engineer – Coordination and Interface Management is responsible for the identification, coordination, and resolution of interfaces between the High-Speed Rail (HSR) project…
Added 5 hours ago
SC
OCS Design Lead
SYSTRA Canada
Toronto, ON
- Full-time
The OCS Lead is an engineering role responsible for leading overhead contact system (OCS) design and delivery for rail and transit infrastructure projects. The position operates within…
Added 5 hours ago
SC
Noise & Vibration Junior Specialist
SYSTRA Canada
Toronto, ON
- Full-time
Lead the subject matter team tasked to complete investigation work and reporting

Urban Ridge Supplies

Principal Software Engineer

Toronto, ON, Canada

Salary Range: $220,000 - $300,000 CAD Our salary ranges are benchmarked and are determined by role and level. · Full-time

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Job details

Pay: Salary Range: $220,000 - $300,000 CAD Our salary ranges are benchmarked and are determined by role and level.
Job type: Full-time
Experience: 7+ years of experience in software development, with a proven track record operating at a Staff or Principal level within a product-driven organization.
Posting language: English
Posted: Sep 24, 2026

Original job description

We’re building applied AI systems for high‑stakes, real‑world decisions. Our platform ingests and reasons over large, messy data to surface evidence with hard constraints around fairness, auditability, and low bias.

The single gnarliest, most impact‑heavy place this problem shows up is in insurance claims, so that’s where we’re deployed today, running in production at some of the largest carriers in North America.

We are seeking a visionary Principal Software Engineer to join our Engineering team. In this role, you will drive our technical strategy, tackle our most complex engineering challenges, and lead the integration of advanced AI models into highly scalable, production-grade features.

We have engineering hubs in New York City and Toronto, and this role is 5 days per week onsite in one of those offices. We optimize for people who like to think deeply, whiteboard with other sharp engineers, and ship ambitious systems together in person.

Join us at Owl.co and become an integral part of a forward-thinking team dedicated to transforming the insurance industry through technology. Your technical leadership will play a crucial role in shaping our product roadmap and delivering massive value to our clients.

Key Responsibilities:

Own the end-to-end system architecture of our core platform, ensuring it is highly scalable, secure, and capable of processing large-scale unstructured data.
Spearhead the engineering effort to seamlessly integrate, scale, and maintain applied AI and machine learning models in a high-stakes production environment.
Partner with Product leadership and cross-functional teams to define the long-term technical roadmap and translate business goals into actionable engineering initiatives.
Act as a technical mentor and force multiplier for engineers across the organization, setting the gold standard for code quality, system design, and engineering best practices.
Take hands-on ownership of the most difficult technical challenges related to system latency, model inference constraints, and complex data pipelines.
Continuously evaluate and introduce new technologies, frameworks, and engineering practices to improve the speed and reliability of our technical stack.

Ideal Profile:

Bachelor's or Master's degree in Computer Science or a related technical field.
7+ years of experience in software development, with a proven track record operating at a Staff or Principal level within a product-driven organization.
Deep, hands-on experience designing, deploying, and scaling AI/Machine Learning systems or LLM-based applications in a production environment.
Experience with Supervised Fine-Tuning (SFT) and Reinforcement Learning (RL) techniques for LLMs and VMs.
Expert-level proficiency in programming languages such as Python, TypeScript or similar.
Exceptional problem-solving skills and the ability to navigate extreme technical ambiguity.
High-level communication skills and the ability to debate architecture with engineers while explaining technical trade-offs to executive leadership.
Extensive experience with cloud platforms such as AWS or Azure.
Deep knowledge of containerized microservices architecture and modern backend APIs.
Experience building software for highly regulated industries where auditability and bias mitigation are critical.
Experience AI coding agents such as Claude Code, Codex, Cursor to accelerate development workflows.

Benefits:

Industry Leaders: Our technical leadership comes from Meta, Microsoft, X, and Goldman Sachs, bringing world-class expertise to our agile team.
Market Leadership: We hold the largest market share in our space, offering a proven ROI and maintaining a 100% customer retention rate, with renewals consistently doubling their previous terms.
Lean & Impact Driven Team: Our small, nimble team makes swift decisions and encourages direct communication and innovation through a flat organizational structure. You’ll make real, meaningful contributions right from the start.
Established Product-Market Fit: AI-Driven Product that helps shape an AI-powered enterprise solution for insurance companies across the US and Canada.
Healthcare benefits: we cover 100% of the premiums for you and 70% for your family members (medical, dental & vision)
RRSP matching to help you save for your future
Recharge: 4 weeks of paid time off & 5 additional personal/sick days
Daily team lunches
Bi-annual offsites: we'll make sure everyone at Owl has an opportunity to hang out with teammates IRL at least twice a year

Salary Range: $220,000 - $300,000 CAD Our salary ranges are benchmarked and are determined by role and level. The range displayed on each job posting reflects a range target for new hire salaries for the position and could be higher or lower based on a multitude of factors, including job-related skills, experience, location, and relevant education or training.

Job Id: Kp0qCVKvHW0TGyUG7F7u7JksdJc7Ztbaxt8JkGMoDnATxmFm6BH0TL+fxNgam/B8JHy9DXFA6e8XS1pOm8ofk4cdZom3ZDV3JfElRROylMGFPqjT8hXX95n2sjMAqmCGbJ76

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More about this job

Responsibilities

The Principal Software Engineer will own the end-to-end system architecture and spearhead the integration of AI and machine learning models into production. They will also partner with leadership to define technical roadmaps and mentor engineering teams to ensure high standards of code quality.

Requirements

Candidates must have 7+ years of experience in software development with a proven track record at a Staff or Principal level. Deep hands-on experience in designing and scaling AI/ML systems in production environments is required, along with proficiency in Python or TypeScript.

Skills

Software architecture
Artificial intelligence
Machine learning
LLM
Python
TypeScript
System design
Cloud platforms
AWS
Azure
Microservices
Data pipelines
Technical leadership
Mentorship
Problem solving
Communication

Benefits

Healthcare benefits
Medical insurance
Dental insurance
Vision insurance
RRSP matching
Paid time off
Personal days
Sick days
Daily team lunches
Bi-annual offsites

Visa sponsorship

Not detected in the job text

Keywords

Principal Software Engineer
Applied AI
Insurance claims
System architecture
Scalability
Production-grade
Machine learning
LLM
Supervised Fine-Tuning
Reinforcement Learning
Python
TypeScript
AWS
Azure
Microservices
Data pipelines
Latency
Model inference
Auditability
Bias mitigation
Claude Code
Codex
Cursor
Technical strategy
Engineering leadership

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