[Hiring] Technical Support Engineer @Siena AI

Role Description

You own the space between our customers and Engineering. As Technical Support Engineer, you take Tier 2+ escalations end-to-end: diagnose, resolve, close. You pull in engineers only when there’s a genuine product bug or infrastructure issue underneath — not as a default path.

You’ll work directly with the e-commerce brands running Siena’s AI agents across complex integration environments. You’ll sit within the Engineering org, report to our Support Manager, and collaborate with Engineering on the issues that actually require them.

What separates this from a senior IC support hire is what happens after the ticket closes. Every Tier 2+ resolution carries two follow-up questions you own:

• Does this pattern belong back in Tier 1?
• How do you build the system so the next instance never escalates, or reaches you faster?

Runbooks, auto-routing, observability access for the Support team — that’s the leverage this role is built to create.

When the Tier 2+ queue is quiet, you work Tier 1 tickets alongside the Support team, staying close to the volume that tells you what to systematize next.

The bar: diagnose it, resolve it, make the system better so it happens less often.

Qualifications

• You have 1+ year of technical support at a SaaS company.
• You debug REST APIs, webhooks, auth flows, JSON, and HTTP protocols.
• You’re fluent in customer-side JavaScript: browser devtools, event handlers, script conflicts, timing issues.
• You write diagnostic SQL to validate data, trace ingestion paths, and answer your own data questions.
• You’re comfortable with production systems: logs analysis, monitoring tools, system debugging.

Requirements

• You have experience with LLMs, prompt engineering, or AI model integration.
• You can triage AI agent behavior and distinguish a prompt/config issue from a model-level problem.
• You’re familiar with how LLM-based systems fail: hallucinations, retrieval gaps, prompt sensitivity, workflow misconfiguration, Custom Action misfires.
• You have experience with AI APIs (OpenAI, Anthropic, etc.).

Benefits

• 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.

Company Description

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.