Principal Software Engineer
$220k - $300k per yearOwl.co
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.
$180k - $300k per year
...committed to making a positive impact on its customers, employees, and communities. The Role We are looking for multiple Principal Software Engineers who are self-starters, love solving technical challenges, and have prior experience working on a variety of engineering...SuggestedRemote jobFull timeWork at officeLocal areaWork from home- ...global company with operating centers in the United States, Canada, the United Kingdom, and India. About the Job: The Principal Software Engineer role at Cyderes reports to the VP of Engineering within the Managed Services department. This role will partner with...SuggestedFull time
- ...and auditing of infrastructure. Mentor senior and mid-level engineers, raise the quality bar through design and code review, and influence... ...how we handle your personal information. ZoomInfo may use a software-based assessment as part of the recruitment process. More...SuggestedContract workWorldwide
$140k - $260k per year
...conference providers using SDKs What you bring: ~7+ years of software development experience using Python ~ Proven experience with... ...: ~ BSc in Computer Science, Mathematics, Software Engineering, or equivalent experience The US base salary range...SuggestedFull time- ...Governance (OIG) organization is looking for a Principal Engineer to join our team — OIG is Okta’s... ...challenge of building enterprise-grade software that millions of users depend on.... ...platforms Familiarity with workflow engines or approval/routing systems (e.g., finite...SuggestedLocal areaRemote workWorldwideFlexible hours
$216k - $297k per year
...times a week. The Auth0Lab Team We are a small team of engineers exploring new Auth0 products and features ideas. We take things... ...ll be doing We are looking for a very senior, knowledgeable Software Architect (P6) that both wants to be hands on and think about...Full timeWork at officeLocal areaWorldwide$196.3k per year
...Do you want to develop more than just a product? Then Jobber might be the place for you! We’re looking for a Mobile Principal Software Engineer to be part of our Software Engineering team. At Jobber, we don’t just build a product - we work on real problems that help people...Long term contractFull timeInternshipWork at office$180k - $300k per year
...committed to making a positive impact on its customers, employees, and communities. The Role We are looking for multiple Principal Software Engineers who are self-starters, love solving technical challenges, and have prior experience working on a variety of engineering...Remote jobFull timeWork at officeLocal areaWork from home$50 - $150 per hour
...include Benchmark , General Catalyst , Peter Thiel , Adam D'Angelo , Larry Summers , and Jack Dorsey . Position: Software Engineer Type: Freelance Compensation: $50–$150/hour Duration: 1–2 months Commitment: 15–25 hours/...Full timeSummer workFreelanceImmediate start- ...security experience, many have been successful at Vanta without it. Vanta is transforming how companies build and scale trust. As a Principal Engineer, you'll define the golden path for frontend development across the organization—establishing patterns, standards, and systems...Full timeManual laborRemote workFlexible hours
$70 - $95 per hour
...include Benchmark , General Catalyst , Peter Thiel , Adam D'Angelo , Larry Summers , and Jack Dorsey . Position: Software Engineer Type: Contract Compensation: $70–$95/hour Location: Remote Role Responsibilities...Full timeContract workSummer workRemote work$85 - $115 per hour
...include Benchmark , General Catalyst , Peter Thiel , Adam D'Angelo , Larry Summers , and Jack Dorsey . Position: Software Engineer IV – Data Collection and Engineering Type: Contract Compensation: $85–$115/hour Location: Redmond,...Full timeContract workSummer work$185k - $230k per year
...experience is an employee first process. Our vision is the same, a place where employees know they can thrive. As an Azure Principal Software Engineer, you will be focused on client engagement, project leadership, and technical solution design of Azure solutions for our...Remote jobFull time$114.3k - $164.3k per year
...drives the core gameplay experience under the hood. We’re looking for outstanding engineers with a passion for technology and the desire to work in a team with dynamic strengths. The Principal Software Engineer will be working with a complementary team of software engineers to...Full timeLocal area$175k - $192.5k per year
...talk. Role Overview We are seeking an accomplished Principal Engineer to lead the technical architecture and evolution of our hybrid... .... Required Qualifications Experience: 8–10 years in software engineering, specializing in SaaS platform architecture and distributed...Local areaWorldwide- ...Principal Software Engineer The global capital markets are among the largest markets in the world valued at $50T+ and growing. Transactions in these markets are complex. Critical, nuanced legal terms are woven into lengthy documents. These documents must be digested and...Long term contractFull timeWork at officeLocal areaFlexible hours2 days per week3 days per week
$180k - $220k per year
...Xello is looking for a Principal Engineer This role is a remote role, looking for candidates within Canada only, working in Eastern Time... ...processes in partnership with our DevOps team, ensuring our software solutions are highly available, performant, and secure. Collaborate...Long term contractFull timeRemote workFlexible hours$120k per year
...actionable insights with lightning speed. We are seeking a Principal Software Engineer to lead the architecture and development of on our Platform... ..., CTEs, and performance tuning across multiple database engines (Redshift, PostgreSQL, Athena). ~ Strong full-stack development...Full timeFlexible hours- ...We are looking for an experienced software engineer to join a team where your work will be front and center to thousands of customers. You will join an elite team who is innovative and flexible; with a weekly, agile release cycle and individual ownership. We expect great...Full timeFlexible hours
$125k - $145k per year
...paperless validation in Life Sciences: valgenesis.com/about The Principal Software Validation Subject Matter Expert (SME) provides strategic and... ...Leadership & Mentorship Collaborate with Quality, IT, Engineering, Manufacturing, QC Labs, and Regulatory Affairs. Mentor...Full timeWork at officeLocal area3 days per week- ...Principal Engineer CoCounsel is our most advanced AI offering to date — combining generative and agentic AI capabilities to help legal... ...professionals move beyond prompting and start delegating. As a Principal Software Engineer focused on Cloud Cost Optimization, you will be the...Full timeWork at officeLocal areaFlexible hours2 days per week3 days per week
- ...Fortune 100, trust the Netskope One platform, its Zero Trust Engine, and the powerful NewEdge network to gain full visibility and... ...products with speed and quality. We are looking for an experienced Principal Software Engineer to own and drive our CI/CD strategy, with a special...
- ...Job Title : Principal Software Developer – Cloud Platform Reporting to : Craig Thorvardson, Director of Software Development, Cloud Platform... ...role is crucial for bridging the gap between Cloud Platform Engineering and development teams , ensuring a balance between...Long term contractFull timeShift workEarly shift
$75 - $80 per hour
...include Benchmark , General Catalyst , Peter Thiel , Adam D'Angelo , Larry Summers , and Jack Dorsey . Position: Software Engineer Type: Freelance Compensation: $75–$80/hour Location: Remote Duration: 1–2 weeks...Full timeSummer workFreelanceImmediate startRemote workFlexible hours$175k - $200k per year
.... Position Summary: The Solution Engineering team is a critical part of League’s growth... ...markets (i.e., Pharmacy Retail). As Principal, Solution Engineering , you serve as... ...Experience in leading solution architecture and software demonstrations for AI-native and/or AI...Full timeWork at officeRemote workFlexible hours$175k - $210k per year
...General Information: Job Title: Principal Engineer - Zynque Location: Toronto (Onsite/ Hybrid) Job Type: Full-Time Hiring Timeline: Immediate Reporting Line: General Manager at Zynque Existing Vacancy: Yes Application Deadline: Open until Filled...Long term contractFull timeInternshipLive InWork at officeImmediate startRemote workFlexible hours$220k - $280k per year
...provider side. Position Summary: League is looking for a Principal Security Engineer to serve as the senior technical leader within our Security... ...workflows Provide technical mentorship to Security Software Engineering and to individuals within Product Security and...Remote jobFull timeWork at officeFlexible hours- ...scale ~️ Build internal platforms and tooling used by AI and engineering teams ~ Reduce manual processes and improve iteration speed on... ...Mentor & Level Up: Bridge the gap between traditional software engineering and AI. You’ll mentor engineers on how to apply rigorous...Long term contractRemplacementFull timeInternshipWork at officeWork from homeShift work
$100k per year
...solutions must evolve to unify innovations in software models, compilers, platforms, networking,... ...looking for an experienced Reliability Engineer to drive and execute reliability testing... ...from wafer to board level. As a Principal Reliability Engineer, you will be expected...Permanent employmentFull timeInternship$150k - $200k per year
...customers, employees, and communities. The Role As a Principal DevOps Engineer for a new product within Veeva, you will be a founding member... ...saving products to market. What You'll Do Provide in-depth software engineering expertise in cloud architecture, design patterns...InternshipWork at officeLocal areaRemote workWork from home
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Principal Software Engineer. Be the first to apply!
- chief engineer Toronto, ON
- project engineer assistant project manager Toronto, ON
- mechanical engineering project manager Toronto, ON
- general engineer Toronto, ON
- engineering project manager Toronto, ON
- director software engineering Toronto, ON
- directeur ingénierie Toronto, ON
- mechanical engineering director Toronto, ON
- chief power engineer Toronto, ON
- développeur logiciel Toronto, ON
