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Staff Software Engineer

2 weeks ago

Toronto, Ontario, Canada Liberate Full time $120,000 - $200,000 per year
About Liberate

Liberate builds AI agents to automate manual tasks for the $2.7T insurance industry. We started with voice — the hardest and most valuable channel in insurance — and are now expanding into full workflow automation across sales, servicing, and claims. Our long-term vision is to build reasoning agents capable of handling the entire spectrum of insurance carrier and broker operations. We've raised $72M to date, including a $50M Series B in October 2025, backed by top-tier venture firms.

About The Role

We are looking for a seasoned Staff Software Engineer to join our development team and help build scalable, reliable, and innovative AI-driven applications. You'll be a key technical leader within the organization, guiding architectural direction, mentoring engineers, and helping shape our next phase of growth.

You will join an amazing team of talented and motivated engineers with diverse backgrounds and experience who value collaboration, learning and improvement, trust and respect, and technical excellence. We believe in creating an environment where teammates enjoy working together, celebrate successes, and have fun solving interesting problems.

Key Responsibilities

  • Define and drive the technical vision for one or more core platforms or domains, including architecture, infrastructure, tooling, and performance.

  • Design, develop, and maintain software applications that leverage foundational LLMs and are built with high performance, scalability, resilience, and observability in mind.

  • Lead cross-functional initiatives: collaborate with data scientists, product managers, other engineering teams, and infrastructure/DevOps to translate business strategy into scalable, technical roadmaps.

  • Serve as a technical mentor and coach: influence coding practices, meet quality standards, perform deep code reviews, share knowledge, and raise the bar for engineering excellence.

  • Actively drive architectural design and trade-off decisions, balancing fast iteration and long-term maintainability. You will gain buy-in from senior stakeholders across the organization and ensure alignment on strategic initiatives.

  • Own operational excellence: troubleshooting, debugging, and resolving issues across the entire stack; lead the on-call rotation; define and measure reliability metrics (SLA/SLO/SLI) and lead post-mortem follow-ups.

  • Evangelize best practices: proactively identify technical debt, propose improvement initiatives, and help deliver them; introduce new technologies and processes that accelerate team productivity and quality.

  • Represent the engineering organization externally when needed (conference talks, open-source contributions, partner engagements) to raise our profile and bring back learnings.

Required Qualifications

  • 8 + years of experience building high-quality production software (Python preferred).

  • Demonstrated experience architecting and delivering asynchronous, high-throughput, distributed systems in production.

  • Strong expertise with FastAPI, Django, asyncio (or similar frameworks) in Python.

  • Proficiency with NodeJS, React, Typescript and/or Express (or equivalent) — with the ability to evaluate when to use which stack and to mentor others.

  • Deep knowledge of SQL and real-time or near-real-time distributed data processing systems (e.g., RabbitMQ, SNS, SQS, Kafka).

  • Strong cloud experience (AWS, Google Cloud, or Azure) and familiarity with DevOps practices, infrastructure as code, monitoring/observability, CI/CD pipelines.

  • Proven ability to navigate ambiguity, make principled trade-offs between speed and quality, and drive innovation while maintaining long-term sustainability.

  • Experience working in a fully remote, asynchronous, distributed team environment; excellent communication skills and ability to influence without authority.

  • Passion for emerging technologies and the curiosity to explore how they apply to real business problems.

Preferred Qualifications

  • Experience working with foundational LLMs (large language models) and understanding of the various approaches to maximizing their efficiency and reliability.

  • Experience in regulated industries (insurance, finance, healthcare) or high-compliance environments.

  • Previous experience in high-growth, fast-paced startup environments where you have helped scale the engineering organization.

  • Proven track record of mentoring senior and mid-level engineers, building high-performing teams, or leading technical communities.

  • Experience in public-facing technical work (open source, conference presentations, publications) is a plus.

If you're excited by the prospect of driving technical direction at a high-growth AI company and helping reshape the insurance industry, we'd love to hear from you.

*Strong preference to be Boston or San Francisco based, but open to remote within the U.S.

Benefits:
  • Competitive salary with equity options
  • Flexible PTO
  • 401(k) plan
  • Comprehensive health, dental, and vision insurance coverage
  • Flexible work environment with remote work options
  • Collaborative and innovative company culture