Technical Support Engineer

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About Siena
Siena is building enterprise empathic AI Agents powered by reasoning-adept LLMs. Siena is the first AI Agent of its kind, designed to integrate with existing systems and interact with customers across multiple channels from a single, unified platform.

About Siena
Siena is building enterprise empathic AI Agents powered by reasoning-adept LLMs. Siena is the first AI Agent of its kind, designed to integrate with existing systems and interact with customers across multiple channels from a single, unified platform.
If you're excited about the intersection of human-to-machine communication and want to be part of a team driving innovation and making a real impact in automating agentic workflows, join us on our mission to revolutionize customer experience through empathetic AI.
Our AI-First Philosophy
At Siena, AI isn't just a tool—it’s embedded in our DNA. We believe that leveraging AI-first workflows empowers individuals to work smarter, faster, and more creatively. Our team embraces AI-powered augmentation in everything we do, from research to execution, making us more efficient and innovative every day.
About The Role
We're seeking an exceptional Technical Solutions Engineer to join our Customer Experience team at Siena. This isn't your typical support role: you'll be solving complex engineering problems that directly impact our customers' success. You'll work at the intersection of customer experience and deep technical problem-solving, becoming the bridge between our customers and our engineering team.
What Makes This Role Special

• Real Engineering Work: Debug production systems, write code, and deploy solutions
• Direct Customer Impact: Your technical expertise directly drives customer success and retention
• Growth Opportunity: Join a rapidly scaling AI company with significant career advancement potential
• Technical Leadership: Own end-to-end technical investigations and become the go-to expert for complex issues
  

What You'll Do
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
  

Who You Are
Technical Skills

• 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
  

AI/LLM Expertise (preferred)

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

Customer-facing Skills

• 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
  

Why Join Us
We’re a startup, so no fancy offices or corporate fluff. But here’s what we do offer:

• Make a real impact. Your work directly shapes our product and company.
• A Voice that matters. In a small team, every perspective counts—yours included.
• Working at Siena. We are a fully remote, globally distributed team working at the bleeding edge of CX and generative AI.
• 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. If you're growing, so are we.
• The thrill of building something new. Join us at a stage where your contributions matter most.
• Tackling meaningful challenges. We’re redefining how work gets done through AI.
  

Our values
We’re not about corporate jargon—here’s what truly matters to us:

• Curiosity and creativity: You always seek new knowledge, ask questions, and explore different perspectives to deepen your understanding.
• Customer empathy: You are driven by our customers’ success. You see needs they can’t articulate.
• Resilience: You bounce back from setbacks, adapt to change, and thrive in the face of challenges.
• Ownership and autonomy: When things break, you fix first, explain later.
• Relationships: You create bonds with your colleagues - building trust and sharing success.
• Craft and speed: You balance vision with pragmatism. Your standards pull everyone higher.
• Open and direct: You share and receive feedback. You are open about what’s working and what not.
  

AI-First Tooling
To ensure you stay at the cutting edge of AI-driven work, we provide:

• Perplexity Pro account
• ChatGPT Pro account
• Claude Pro account
• Quarterly budget for experimenting with new AI tools
• A culture that encourages AI experimentation and adoption
  

We encourage our team to explore and integrate AI tools into their workflows, allowing them to maximize efficiency and innovation in their roles.
At Siena, we’re not just looking for people who can do a job. We’re looking for people who want to break boundaries, create the future, and reshape industries. If that’s you, we look forward to your application.
Siena provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.
Seniority level

• Seniority level Mid-Senior level

Employment type

• Employment type Full-time

Job function

• Job function Information Technology
• Industries Technology, Information and Internet

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