Principal Software Engineer

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.