Job Description Toast is recruiting on behalf of this company for a Senior Software Engineer, AI to join their Engineering team in Toronto. They are looking for an experienced backend engineer who is excited to build and optimize LLM-powered systems that help users uncover meaningful business insights.

In this role, you will lead the design and development of search, retrieval, and agentic workflows that transform large volumes of competitive data into trusted, actionable intelligence. This company is seeking someone who can own projects end to end, make thoughtful architectural decisions, and help shape the future of AI-powered product experiences at scale.

This is an opportunity to work on complex, high-impact problems in a collaborative environment where curiosity, ownership, and continuous learning are valued. This company welcomes candidates who may not meet every listed qualification but can demonstrate strong potential and relevant experience.

Responsibilities

• Design, build, and maintain backend systems that power LLM-driven and agentic workflows
• Develop retrieval pipelines, orchestration layers, and multi-step agent architectures that support scalable AI-powered search experiences
• Lead the evaluation of agentic systems using automated, offline, and human-in-the-loop frameworks to measure relevance, quality, latency, and task success
• Improve retrieval and ranking systems across hybrid retrieval, re-ranking, query rewriting, and post-retrieval synthesis
• Optimize LLM-powered workflows for speed, accuracy, reliability, and production readiness
• Own technical projects from concept through launch, including experimentation strategy, architecture decisions, and operational excellence
• Collaborate closely with product, infrastructure, and data teams to align technical solutions with user needs and business goals
• Stay current with advances in LLMs, retrieval systems, and agentic reasoning, and apply relevant developments to product and engineering work
• Contribute to engineering best practices that support maintainability, observability, testing, and continuous delivery

Requirements

• 5+ years of experience building and operating backend systems in production
• Strong experience in at least one of the following areas: search and retrieval, data pipelines, distributed systems, or API-driven service architectures
• 2+ years of hands-on experience working with search, retrieval, or ranking systems
• Experience building or evaluating LLM-powered or agentic systems, including retrieval-augmented generation or multi-step workflows
• Strong software engineering fundamentals with the ability to write clean, maintainable, and well-tested code
• Proficiency in Python and experience with backend frameworks, APIs, and production infrastructure
• Familiarity with vector databases and search platforms such as FAISS, PGVector, Pinecone, Weaviate, Elasticsearch, or OpenSearch
• Experience with cloud platforms such as AWS, GCP, or Azure in environments with scale, low-latency requirements, and high availability
• Experience using AI coding tools to improve development workflows
• A customer-focused mindset with the ability to connect technical decisions to user outcomes
• Demonstrated ability to lead projects, make sound architectural decisions, and support the growth of others on the team

Benefits

• Competitive compensation with a salary range of CA$145,000–CA$183,000, plus equity
• Extended health and dental coverage starting from day one
• Employee Stock Option Plan for full-time employees
• Flexible vacation policy designed to support rest and balance
• Career development support through coaching, feedback, and performance reviews
• Access to high-quality equipment and tooling
• Hybrid work model with in-office collaboration in Toronto on designated days
• Opportunities to work closely with leadership and contribute to meaningful technical direction
• A workplace that values belonging, authenticity, accessibility, and professional growth
• An inclusive hiring approach that considers potential, transferable experience, and equivalent backgrounds
• Application Review

Submit your application, including your resume and cover letter, through our online portal. Our team will carefully review your qualifications and experiences. We take pride in responding promptly, so if your application aligns with our current opportunities, you’ll hear back from us with next steps. Your journey with Toast begins here, and we’re excited to see what you bring to the table!

• Vetting Call

If your application is successful, we’ll schedule a vetting call with a member of the Toast team. This 30-45 minute informal conversation is designed for us to get to know you better and assess your skills. Be prepared to discuss your past projects, the challenges you’ve tackled, and the impact you’ve made. This is your chance to shine and show us why you’re a great fit for the roles we offer.

• Profile Creation

Once you’ve impressed us in the vetting call, we’ll create an unbiased profile that highlights your experience while minimizing common biases. Instead, we focus on your skills, industry experience, and the impact you’ve made. This way, your profile reflects your true potential and accomplishments.

• Client Submission

After crafting your unbiased profile, we submit it to our trusted clients. We work closely with these clients to ensure they understand the value you bring. Throughout their interview process, we remain by your side, providing support and guidance. Our goal is to help you navigate the hiring process smoothly and confidently, ensuring you have the best chance to secure a role that fits your skills and aspirations.