Siena AITechnical Support Engineer
Meet Siena
Siena is the first intelligence layer for customer experience. We're creating an operating system of AI agents that learn, remember, and act across every customer touchpoint—from support conversations to shopping experiences to voice and social media interactions.
Siena doesn't just automate support; it powers shopping agents, builds persistent customer memory, generates actionable business insights, and creates empathetic interactions that feel human.
We're transforming how businesses understand and connect with their customers, turning every interaction into intelligence that makes the next one better.
The team
We're a small, distributed team that punches way above our weight. Every person here has outsized impact because we've built leverage into everything we do. This philosophy makes us faster and, frankly, more fun to work with.
If you're excited about building something that doesn't exist yet, keep reading. We're building agents that don't just respond to customers—they remember them, learn from every interaction, and connect experiences across channels.
About the Role
We're seeking an exceptional Technical Support 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
1+ year of software engineering experience with production systems in a SaaS environment
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 Siena?
Meaningful impact. Your work directly shapes our product and company.
Globally distributed team working at the bleeding edge of CX and AI.
Great salary plus the opportunity for equity or stock grants.
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.
AI-fluency. Make AI your second nature.
Tackle unsolved problems. We’re redefining how customer experience will look like in the next decades.
Our values
The people who thrive here are curious, customer-obsessed, and take ownership without being asked. They fix problems first and explain later. They're direct about feedback—both giving and receiving it—because they care more about getting things right than being polite.
They maintain high standards while moving at startup speed, and they build real relationships with teammates because they know that's how great work gets done. When things get tough, they adapt and keep pushing forward.
Our approach to AI
The people who thrive here treat AI like a natural extension of themselves. They've built their own ecosystem of agents - some for research, others for debugging, writing, analysis, or writing code. They know which AI works best for what problem.
Everyone gets premium accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) plus a quarterly budget for new tools. But the magic happens in how we share knowledge. Demo days where someone shows off a clever workflows. Slack threads about which model handles a specific use case better. Learning from each other's AI workflows.
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.