Senior Software Engineer - Canada

Senior Software Engineer

Remote role based in Canada. Must work at least 6 hours of overlap with US Eastern Time.

What We Do

The company is a modern pet healthcare company built around how pet parents actually care for their pets. We partner with employers to provide a complete approach to pet and pet-parent wellbeing, from preventive wellness plans and emergency coverage to 24/7 pet telehealth guidance. Our purpose is to unlock every pet parent's potential to provide extraordinary care, and we do it by bringing the same intentionality to pet benefits that the best employers bring to human healthcare. Founded in 2017 and female-founded, the company is headquartered in New York City and trusted by leading employers nationwide.

What’s Important To Us

Our mission shapes everything we build and how we work together. We take fearless ownership of outcomes, collaborate with radical candor, and are always driven by the customers and pet parents who trust us. We think critically, follow through relentlessly, and find the extra 10% that turns good work into exceptional work. We keep it weird because the obvious answer is rarely the most interesting one. Our values aren't aspirational. We interview for them and hold each other accountable to them. If what you've read so far resonates with you and you want to be part of a team where every person makes the company meaningfully better, we'd love to hear from you..

About The Role

The company uses AI to process pet wellness and insurance claims. When it works, a pet parent submits a claim and gets reimbursed without anyone on our team touching it. We already automate a meaningful share of claims, and we’re hiring a Senior Software Engineer to take that much further.

You’ll join our Pet Parents squad and take on our claims automation system, the pipeline that reads invoices, decides what’s covered, and pays claims. In your first year, you’ll make it cheaper to run, easier to change, and able to handle claims it can’t handle today. You’ll own that work from design to production and partner with Product on what to build next.

This role is for someone who has shipped AI features that real users and real money depend on, and who knows the difference between a demo and a system you can trust.

Our Tech Stack: Python · Django · TypeScript · React · LLM APIs · OpenRouter · LangSmith · GitHub · Linear · Claude Code · CodeRabbit

Core Responsibilities

• Learn our claims automation pipeline in depth and become a core owner, reviewing and shipping changes on your own within your first few months.

• Lower the cost of every claim we process by routing work to the right models, while keeping accuracy at or above where it is today.

• Restructure the pipeline so each stage can be changed, tested, and rolled out independently, with evaluations gating every change.

• Ship new automation that lets more claims resolve without manual review, working with Product to decide what comes next.

• Use AI to read veterinary records and make better coverage decisions on more types of claims.

What You’ll Need To Be Successful

• You’ve shipped an LLM-powered feature to production that real users or real money depend on. You set up evaluations before rollout, versioned your prompts and models, and planned for rollback.

• You’ve designed or substantially refactored a system the business depends on, such as payments or claims, without breaking it, and left it easier to change than you found it.

• You’ve taken over a complex system someone else built and become the person others trust with it. Your code reviews change designs, not just style.

• You’ve made real tradeoffs between model cost and quality, and you can show the numbers that proved quality held.

• You use coding agents and AI review tools every day, and they’ve changed how fast you ship without lowering the quality of your work.

• Strong Python skills. Experience with Django and TypeScript is a plus.

Why Consider This Role?

• Your work pays real claims to real pet parents. You’ll see the impact in production.

• AI is the core of the product here, not a side project. You’ll own one of the most important systems at the company.

• You’ll have real scope on a small team, making decisions a larger company would spread across several people.

• You’ll help pet parents get reimbursed faster for the care their pets need.

Key Benefits

• Comprehensive health, vision, and dental coverage

• HSA/FSA

• 401(k) retirement planning with employer matching

• Unlimited paid time off

• Annual company holidays

• Additional company-wide recharge days off

• 12 weeks parental leave for eligible employees

• Company paid the company pet wellness and insurance plans

• Regular company-wide events and team gatherings

• Pet-friendly office

• Catered lunches

We here at the company strive to build a workforce composed of individuals with diverse backgrounds, abilities, minds, and identities that will help us to grow, not only as a company, but also as individuals. The company is an Equal Opportunity Employer.