Senior AI Agent & Evaluations Engineer
ChatGPT Jobs · Portland, OR · 3 wk ago
Business DevelopmentFull-time
Key Responsibilities
- Design, refine, and optimize prompts, tool definitions, routing logic, and decision-making behavior across Vacatia's AI agent ecosystem
- Build and maintain evaluation frameworks, golden datasets, grading systems, and regression testing pipelines
- Develop guardrails and safe-failure mechanisms for customer-facing and financially sensitive workflows
- Monitor production performance, investigate failures, identify edge cases, and improve agent outcomes through data-driven iteration
- Partner with business stakeholders to translate policies and domain expertise into measurable agent behavior
- Collaborate with engineering teams on context requirements, tool contracts, and integration specifications
- Create scalable frameworks and reusable patterns for deploying AI agents across new workflows
- Establish best practices for prompt engineering, evaluation methodologies, observability, and agent operations
Requirements
- Proven experience shipping and owning production AI agents or LLM-powered systems beyond proof-of-concept
- Deep expertise in prompt engineering (system prompts, tool usage, context management, output constraints, agent behavior design)
- Hands-on experience building evaluation frameworks using golden datasets, scoring rubrics, LLM-as-judge methodologies, and regression testing
- Strong familiarity with modern AI development tools (Claude Code, Codex, or similar coding agents)
- Experience with agent observability and evaluation platforms (LangSmith, Langfuse, Arize, Galileo, or comparable)
- Able to distinguish prompt issues from data, tooling, model, or evaluation failures
- Strong written and verbal communication skills
- Demonstrated ownership mindset with passion for reliable, measurable AI systems
Strongly Preferred
- Experience building agents for communication-based workflows (emails, support tickets, chat interactions, transcripts)
- Experience with multiple agent frameworks and understanding of their tradeoffs
- Familiarity with the evolving LLM landscape and model selection strategies
- Experience designing end-to-end evaluation pipelines and agent operations workflows
- Production experience with online evaluation systems and automated scoring of live traffic
Nice to Have
- Experience integrating AI systems with Salesforce, AWS Connect, or customer engagement platforms
- Background in customer-facing industries requiring accuracy, compliance, and communication quality
- Contributions to open-source projects, technical writing, or public thought leadership in AI/prompt engineering/agent development