About Rentsync:
Rentsync is an award-winning, high-growth organization that provides high quality websites, marketing services, and software solutions to the rental and property management industry throughout Canada and the United States.
About the Role:
We're building the AI products that will define the next decade of rental housing technology. We're looking for a senior engineer who doesn't just use AI tools, but ships production systems on top of them.
What you'll build:
- Software features and products in the rental housing / proptech landscape
- Production LLM-powered features and agents
- Eval harnesses, prompt versioning, and observability
- Integrations via MCP and APIs
Stack you may work with:
TypeScript / Node · React / VueJS / Vite / Tailwind · PostgreSQL / MySQL / MsSQL · Python · CloudFlare · AWS · Azure · MCP · and more
This is a hybrid/remote position, all qualified candidates are encouraged to apply, however preferential consideration may be given to individuals who can report to one of Rentsync’s regional offices (located in Toronto, St. Catharines and Montreal) 2 days per week on average. Only candidates who currently reside in and are authorized to work in Canada are eligible to be considered for this role.
Duties & Responsibilities:
- Design, develop, test, and maintain scalable web applications across the full stack
- Write clean, maintainable, well-tested, and well-documented code following established best practices
- Participate in architectural discussions and contribute to technical design decisions
- Design, maintain, and optimize database schemas and queries
- Develop and maintain background processing and job queues
- Integrate and maintain third-party APIs and external service integrations
- Implement caching strategies and performance improvements
- Monitor, troubleshoot, and resolve production issues in a timely manner
- Participate in code reviews to ensure code quality, security, and adherence to standards
- Collaborate with product managers, designers, and stakeholders to translate business requirements into technical solutions
- Contribute to sprint planning, estimation, and Agile ceremonies using Jira
- Maintain application security best practices, including proper authentication, authorization, and data protection
- Assist in deployment and environment configuration across cloud infrastructure, with applications containerized using Docker
- Continuously evaluate and recommend improvements to systems, tooling, and development processes
- Design and ship AI products
- Collaboratively establish patterns others adopt; reference implementations, scaffolding, standards
- Partner with product and operations
Required Knowledge, Skills & Abilities:
- Strong backend development skills and comfort across modern frontend frameworks
- Sound judgment on reliability, cost, latency, and security trade-offs in AI systems
- You build with AI daily
- Senior-level communication: you can explain a trade-off to an engineer and a stakeholder in the same meeting
- Experience designing and consuming RESTful APIs (GraphQL a plus)
- Strong analytical, debugging, and problem-solving skills
- Effective communicator, able to collaborate across engineering, product, and design
- Proficiency with Git and collaborative workflows using GitHub
Essential Qualifications:
- 6+ years building and shipping production software, with a track record of owning systems end to end
- Hands-on experience putting LLMs into production; RAG, agents, tool use, structured outputs, evals
Additional Preferred Qualifications
- Workplace experience Python for ML / data work
- Workplace experience with autonomous or multi-step agents in production
- Background in proptech, marketplaces, or high-volume consumer platforms
- Familiarity with Cloudflare's platform (Workers, Zero Trust)
- Experience standing up AI observability and eval tooling
Rentsync is an equal opportunity employer. If you are selected to participate in the interview process and require unique accommodations, please don’t hesitate to let us know.
Successful candidates may be required to complete a criminal background check in the final phase of the interview process.
This is an open-ended job posting and may not represent a specific vacancy within the organization.
Rentsync reserves the right to use Artificial Intelligence to screen and/or assess candidates.
Rentsync Toronto, Ontario, CAN Office
672 Dupont St, Toronto, Ontario, Canada, M6G 1Z6
