The AI Engineer will design, develop, and deploy AI-powered systems, improve operations with intelligent workflows, and collaborate on high-leverage AI opportunities.
At Portless, we specialize in global delivery solutions for SMBs and enterprise merchants, enabling businesses to ship direct-from-factory from manufacturing hubs like China to destinations worldwide. As an AI Engineer, you will own the design, development, and deployment of AI-powered systems that make our operations faster, our team smarter, and our merchants more successful — from intelligent automation and agentic workflows to LLM integrations embedded across our product and internal tooling. If you're passionate about building AI systems that create real business impact, thrive in fast-moving environments, and want to work at the intersection of logistics and cutting-edge AI, we'd love to meet you.
Responsibilities:
- Design and build AI-powered features across our B2B portal, internal tooling, and merchant-facing products — including LLM integrations, AI agents, and intelligent automations
- Translate ambiguous business problems into well-scoped AI solutions, from prompt engineering and RAG pipelines to full agentic workflows
- Build, evaluate, and iterate on AI systems using a rigorous experiment-driven approach — tracking quality, latency, and cost tradeoffs
- Collaborate closely with product, operations, and engineering teams to identify high-leverage AI opportunities and deliver them end-to-end
- Develop internal AI tooling and skill frameworks that empower non-technical teams to leverage AI in their daily workflows
- Integrate with third-party AI APIs (Anthropic, OpenAI, etc.) and MCP-based tooling while maintaining security and reliability standards
- Maintain observability over deployed AI systems — monitoring for regressions, prompt drift, and model performance degradation
- Work independently in a remote environment with a strong sense of ownership and ability to ship with minimal oversight
Requirements:
- 3+ years of software engineering experience, with at least 1–2 years focused on building production AI or ML systems
- Hands-on experience with LLM APIs (Anthropic Claude, OpenAI GPT, etc.) and prompt engineering best practices
- Strong programming skills in Python and/or TypeScript/JavaScript; comfortable building both backend services and lightweight frontend interfaces
- Experience building RAG pipelines, embedding workflows, or agentic systems using frameworks like LangChain, LlamaIndex, or similar
- Familiarity with vector databases (Pinecone, Weaviate, pgvector, etc.) and semantic search patterns
- Experience working cross-functionally with non-technical stakeholders to scope and deliver AI projects
- Proven ability to evaluate AI output quality and build evals/testing frameworks for LLM-based systems
- Logistics, supply chain, or B2B SaaS experience is a strong plus
- Experience with MCP (Model Context Protocol), AI agent orchestration, or multi-step tool-use workflows is a bonus
Portless Toronto, Ontario, CAN Office
120 Adelaide St West , 2500, Toronto, ON, Canada, M5H 1P9
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