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

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:

1) Does this pattern belong back in Tier 1?

2) 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.

What You’ll Do

Own technical resolution end-to-end

• You take full ownership of Tier 2+ escalations. You diagnose and resolve without pulling in engineers unless there’s an actual product bug or infrastructure issue underneath.

• You debug API integrations independently: auth failures, webhook issues, data sync gaps, rate limiting, intermittent failures, provider-specific limitations.

• You diagnose and resolve customer-side JavaScript issues: widget behavior, event tracking, data passing, script conflicts, cross-browser bugs.

• You triage AI and chatbot behavior — wrong answers, workflow misconfiguration, hallucination patterns, Custom Action misfires — tracing whether the issue is prompt, KB, workflow config, or model.

• You run diagnostic SQL on data discrepancies, missing records, and report mismatches.

• When the escalation queue is clear, you work Tier 1 tickets alongside the Support team, staying close to the patterns that tell you what to systematize next.

Build leverage, not just resolution

• After every Tier 2+ resolution, you ask: can this move back to Tier 1? If a pattern can be handled by the Support team with a runbook or training, you move it back.

• You build and maintain internal documentation for common failure modes, turning one-off resolutions into team-wide capability.

• You scope and drive systemic improvements: auto-routing, observability access, tools that turn recurring manual tasks into repeatable systems.

• You surface patterns, recurring bugs, and product gaps to Engineering systematically — not ad hoc.

Own the customer-facing experience

• You own complex technical issues directly with customers. You’re the technical face of Siena when depth is required.

• You translate complex technical problems into clear explanations for customers and non-technical teammates.

• You manage expectations confidently through multi-step debugging processes.

• You escalate to Engineering only when an issue genuinely requires a code fix, infrastructure access, or schema migration.

Work at the edge of AI-native infrastructure

• You support customers integrating with Siena’s AI agents across Shopify, Gorgias, Zendesk, Kustomer, Gladly, and custom environments.

• You troubleshoot LLM-based agent behavior, integration edge cases, and platform failures.

• You use AI tools actively in your diagnostic workflow. You’re not just supporting AI products — you’re fluent in them.

Who You Are

Technical skills

• You have 1+ year of technical support at a SaaS company. You’ve owned hard technical threads end-to-end, from customer report to closed ticket, without handing the thread to engineering.

• You debug REST APIs, webhooks, auth flows, JSON, and HTTP protocols. You find the break and distinguish customer-side cause from product cause.

• You’re fluent in customer-side JavaScript: browser devtools, event handlers, script conflicts, timing issues. You’re comfortable using AI coding tools like Claude Code to navigate unfamiliar codebases quickly.

• You write diagnostic SQL to validate data, trace ingestion paths, and answer your own data questions without waiting on a data team.

• You’re comfortable with production systems: logs analysis, monitoring tools, system debugging.

AI/LLM expertise (preferred)

• 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.).

Customer-facing skills

• Your written and verbal English is strong. You explain complex technical issues to non-technical stakeholders without losing them.

• You build trust quickly. Customers feel like their problem is in capable hands.

• Empathy and urgency coexist naturally for you.

• You work independently in a remote environment with strong async communication.

Built for startup pace

• You’re comfortable in ambiguity. You create structure where there isn’t any.

• The leverage mindset is already a habit: when you talk about past wins, you naturally mention what you did so the next instance wouldn’t escalate — not just how you fixed the ticket.

• You’ve coached or trained non-technical teammates. Pairing sessions, documentation that got used, concrete evidence of being a multiplier.

• You're available to cover North America timezones

What Success Looks Like

90 days

• Engineers are no longer pulled into support escalations. Tier 2+ resolution is yours by default.

• Tier 2+ resolution time baseline is established and surfaced.

• You’ve mapped the most common technical failure patterns across the customer base.

• At least one Tier 2 pattern has moved back to Tier 1 with a runbook the Support team is actively using.

• You’ve built a working partnership with the Support Manager and are co-prioritizing what to systematize next.

6 months

• Resolution time is measurably improving from the 90-day baseline.

• CSAT on technical issues is improving.

• Engineering is fully protected from support interruptions.

• The feedback loop to Engineering is running systematically — patterns, bugs, and product gaps surfaced before things break loudly.

• The Support team is resolving more independently. Your internal documentation covers the most common failure modes.

• You’ve shipped at least one systemic improvement project: auto-triage, observability access, or equivalent.

Nice to Have

• You’ve supported AI or LLM-based products before: hallucination patterns, prompt sensitivity, retrieval-grounded responses.

• You have a background in e-commerce or DTC and understand the merchant world: catalog, orders, fulfillment, returns.

• You’re familiar with modern observability tooling: Honeycomb, Grafana, Splunk, Sentry, Kibana, or equivalents.

• You’ve built internal tooling or automation to improve support workflows — a triage bot, runbook generator, custom dashboard, or anything that turned a recurring manual task into a repeatable system.

• You’re fluent with Claude Code or equivalent AI coding tools. Your value is judgment about when to automate and how to verify output, not syntax recall.

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.

We use AI-assisted screening tools as part of our hiring process. All decisions are made by humans. You can request a human-only review at talent@siena.cx.

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.