Senior Software Engineer; Infrastructure

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’re looking for an experienced Software Engineer (Infrastructure) who wants to own core systems end‑to‑end, not just close tickets. You’ll design, implement, and evolve the infrastructure that keeps our AI products fast, reliable, and secure from AWS architecture and networking, to observability, performance, and deployment pipelines for real‑time decisioning. You’ll work in a small, senior team where you can actually shape architecture, tooling, and engineering standards, and see your decisions show up directly in what ships to customers.

We have engineering hubs in New York City and Vancouver, 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.

• Design, develop, and maintain scalable infrastructure solutions using AWS services.
• Implement infrastructure as code (IaC) using tools such as Terraform, Cloud Formation, or similar.
• Automate deployment, monitoring, and management of infrastructure.
• Collaborate with software development teams to ensure seamless integration and deployment of applications.
• Monitor and optimize infrastructure performance, scalability, and security.
• Troubleshoot and resolve infrastructure-related issues.
• Implement best practices for security and compliance.
• Participate in on‑call rotation and incident management.

• 3-6 years of experience as a Software Engineer with a focus on infrastructure.
• Strong proficiency in AWS services such as EC2, S3, RDS, Lambda, and VPC.
• Experience with infrastructure as code (IaC) tools like Terraform or Cloud Formation
• Proficiency in scripting languages such as Python, Bash, or similar.
• Familiarity with CI/CD tools and practices.
• Strong understanding of networking concepts, security principles, and cloud architecture.

• 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) 🩺
• 401K / 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 🚀

Base Salary Range: $150,000 - $250,000 local currency

Our salary ranges are benchmarked and are determined by role and level. The range displayed on each job posting reflects the minimum and maximum target for new hire salaries for the position across all locations and could be higher or lower based on a multitude of factors, including job‑related skills, experience, location, and relevant education or training.

Join us at  and be part of a dynamic team driving innovation in the insurance industry. If you’re passionate about leveraging AI to tackle real‑world challenges and eager to make a meaningful impact, we’d love to hear from you!