Technical Support Engineer

Summary

Join Siena, a company building enterprise empathic AI Agents, as a Technical Solutions Engineer. This role goes beyond typical support; you will solve complex engineering problems impacting customer success, bridging the gap between customers and the engineering team. You will engage in real engineering work, directly impacting customer success and offering significant growth opportunities. The position involves technical leadership, owning end-to-end investigations and becoming an expert on complex issues. Siena offers competitive compensation, flexible time off, a learning budget, and the chance to build something new while tackling meaningful challenges. The company values curiosity, customer empathy, resilience, ownership, relationships, craft, speed, and open communication.

Requirements

• 3+ years of software engineering experience with production systems
• Strong programming background in JavaScript, Python, or similar languages
• API debugging expertise - REST APIs, JSON, HTTP protocols, authentication
• Production systems experience - logs analysis, monitoring tools, system debugging
• Database knowledge - SQL queries, data analysis, performance troubleshooting
• Excellent English communication (written and verbal)
• Experience explaining technical concepts to non-technical stakeholders
• Problem-solving mindset with customer empathy
• Ability to work independently in a remote environment
• Work NA time zones - 9:00 AM EST - 6:00 PM EST

Responsibilities

• Technical problem solving
• Debug complex API failures, LLM hallucinations, and integration bugs using production tools
• Analyze system traces in Honeycomb and other observability platforms
• Write and deploy JavaScript code snippets for customer website integrations
• Perform root cause analysis on system-level issues and data inconsistencies
• AI & LLM expertise
• Troubleshoot and optimize prompt engineering configurations
• Diagnose LLM response issues and implement solutions
• Work with AI model behaviors and performance optimization
• Debug autonomous agent workflows and decision-making processes
• Integration & development
• Fix customer integration issues through code modifications
• Deploy and maintain JavaScript implementations for Live Chat and Shopping Agent features
• Work with REST APIs, webhooks, and third-party integrations
• Create technical documentation and implementation guides
• Customer Engineering
• Conduct technical deep-dives with customer engineering teams
• Lead complex technical implementations and migrations
• Provide architectural guidance for customer integrations
• Escalate and collaborate with Product Engineering only when necessary
• Process & documentation
• Own technical investigations from initial report to final resolution
• Create detailed technical documentation and runbooks
• Build debugging workflows and troubleshooting guides
• Contribute to internal tools and automation

Preferred Qualifications

• AI/LLM expertise
• Experience with LLMs, prompt engineering, or AI model integration
• Understanding of machine learning concepts and model behavior
• Experience with AI APIs (OpenAI, Anthropic, etc.)

Benefits

• Competitive compensation
• Great salary plus the opportunity for equity or stock grants
• Flexible time off
• Take at least 15 days—more if you need it
• A Learning budget
• Perplexity Pro account
• ChatGPT Pro account
• Claude Pro account
• Quarterly budget for experimenting with new AI tools