Senior Software Engineer
2 hours ago
Winnipeg, Manitoba, Canada
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Full-time
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At Cloudbeds , we're not just building software, we're transforming hospitality. Our platform powers hotels across 150 countries, processing billions in bookings annually. From boutique properties to large hotel groups, we help hoteliers transform operations and uplevel their commercial strategy through a unified platform that integrates with hundreds of partners. And we do it with a completely remote team. Imagine working alongside global innovators to build AI-powered solutions that solve hoteliers' biggest challenges. Since our founding in 2012, we've continually been recognized for excellence, most recently earning top honors at the 2026 HotelTechAwards for Best Hotel Management Software and landing on Deloitte's Technology Fast 500 again, but we're just getting started.
As a Senior Software Engineer on the Core AI Squad, you'll design, build, and operate customer-facing AI platform capabilities that power intelligent product experiences across Cloudbeds. This is a product engineering role focused on production AI systems, agentic workflows, evaluation, and observability - not an internal tooling role. You'll work primarily in Python while collaborating across our broader PHP and Java ecosystem, building systems where correctness, reliability, latency, cost, and model quality are core to the job. Your goal is to help Cloudbeds ship AI-powered customer experiences that are useful, trusted, scalable, and measurable.
The Core AI Squad owns the customer-facing AI platform infrastructure, agentic workflows, and evaluation and observability foundations that enable AI-powered experiences across Cloudbeds products. The team builds the production capabilities that let us evaluate models and providers for specific use cases, orchestrate tools and workflows, measure quality over time, and integrate AI safely into real customer journeys. You'll join a senior, product-minded group that values ownership, pragmatic architecture, fast learning, and strong collaboration across product, design, data, and engineering.
Design, build, and operate customer-facing AI platform services and product features primarily in Python, while integrating with PHP and Java systems as needed
Build and evolve agentic harnesses, including agent runtimes, workflow orchestration, tool execution, state management, recovery paths, and evaluation hooks
Integrate agents and LLM-powered workflows into production systems with strong attention to reliability, correctness, latency, scalability, and cost
Evaluate models and providers for specific product use cases, using clear success criteria and abstractions that keep the platform flexible as the AI ecosystem evolves
Own evaluation, tracing, observability, and quality feedback loops for AI features so the team can detect regressions, understand behavior, and improve over time
Write clean, well-tested, well-documented code and advocate for engineering best practices, test automation, maintainability, and operational excellence
Collaborate with product, design, data, security, and engineering partners to turn ambiguous AI product opportunities into reliable customer-facing features
Comfort building, debugging, and operating services that interact with PostgreSQL, SQS, gRPC, and REST APIs, including data models, event streams, service contracts, and versioning
Contribute as a senior individual contributor through technical leadership, architecture input, pair programming, code reviews, and mentorship
5+ years of software engineering experience building, shipping, and operating production systems
Strong proficiency with Python in production environments, including APIs, services, tests, debugging, and operational ownership
Hands-on experience building, integrating, or evaluating agentic systems, agent harnesses, tool orchestration, or LLM-powered workflows
Experience with agentic frameworks and tooling such as LangChain, LangSmith, LangGraph, or similar platforms (PydanticAI, CrewAI, etc)
Experience with MCP, vector databases, retrieval patterns, RAG architectures, or AI evaluation platforms
Comfortable working across a polyglot stack, especially contributing to or integrating with PHP and Java services when the product requires it
Familiarity with prompt and version management, guardrails, tracing, LLM observability, cost and latency optimization, or human-in-the-loop workflows
Experience with cloud infrastructure and containerization such as Docker, Kubernetes, and AWS, plus experience working with remote-first, globally distributed teams
Experience with API-driven design, distributed systems, data modeling, and reliable service boundaries
Strong knowledge of software best practices, design patterns, performance, security-minded development, and testing across unit, integration, and end-to-end levels
Excell
As a Senior Software Engineer on the Core AI Squad, you'll design, build, and operate customer-facing AI platform capabilities that power intelligent product experiences across Cloudbeds. This is a product engineering role focused on production AI systems, agentic workflows, evaluation, and observability - not an internal tooling role. You'll work primarily in Python while collaborating across our broader PHP and Java ecosystem, building systems where correctness, reliability, latency, cost, and model quality are core to the job. Your goal is to help Cloudbeds ship AI-powered customer experiences that are useful, trusted, scalable, and measurable.
The Core AI Squad owns the customer-facing AI platform infrastructure, agentic workflows, and evaluation and observability foundations that enable AI-powered experiences across Cloudbeds products. The team builds the production capabilities that let us evaluate models and providers for specific use cases, orchestrate tools and workflows, measure quality over time, and integrate AI safely into real customer journeys. You'll join a senior, product-minded group that values ownership, pragmatic architecture, fast learning, and strong collaboration across product, design, data, and engineering.
Design, build, and operate customer-facing AI platform services and product features primarily in Python, while integrating with PHP and Java systems as needed
Build and evolve agentic harnesses, including agent runtimes, workflow orchestration, tool execution, state management, recovery paths, and evaluation hooks
Integrate agents and LLM-powered workflows into production systems with strong attention to reliability, correctness, latency, scalability, and cost
Evaluate models and providers for specific product use cases, using clear success criteria and abstractions that keep the platform flexible as the AI ecosystem evolves
Own evaluation, tracing, observability, and quality feedback loops for AI features so the team can detect regressions, understand behavior, and improve over time
Write clean, well-tested, well-documented code and advocate for engineering best practices, test automation, maintainability, and operational excellence
Collaborate with product, design, data, security, and engineering partners to turn ambiguous AI product opportunities into reliable customer-facing features
Comfort building, debugging, and operating services that interact with PostgreSQL, SQS, gRPC, and REST APIs, including data models, event streams, service contracts, and versioning
Contribute as a senior individual contributor through technical leadership, architecture input, pair programming, code reviews, and mentorship
5+ years of software engineering experience building, shipping, and operating production systems
Strong proficiency with Python in production environments, including APIs, services, tests, debugging, and operational ownership
Hands-on experience building, integrating, or evaluating agentic systems, agent harnesses, tool orchestration, or LLM-powered workflows
Experience with agentic frameworks and tooling such as LangChain, LangSmith, LangGraph, or similar platforms (PydanticAI, CrewAI, etc)
Experience with MCP, vector databases, retrieval patterns, RAG architectures, or AI evaluation platforms
Comfortable working across a polyglot stack, especially contributing to or integrating with PHP and Java services when the product requires it
Familiarity with prompt and version management, guardrails, tracing, LLM observability, cost and latency optimization, or human-in-the-loop workflows
Experience with cloud infrastructure and containerization such as Docker, Kubernetes, and AWS, plus experience working with remote-first, globally distributed teams
Experience with API-driven design, distributed systems, data modeling, and reliable service boundaries
Strong knowledge of software best practices, design patterns, performance, security-minded development, and testing across unit, integration, and end-to-end levels
Excell