Meet Siena

Siena is the Agent of Record for consumer brands. One agent that owns the entire customer journey running on a shared intelligence layer no point tool can replicate.

Consumer brands run ten or more disconnected tools to manage their customers. We collapse that stack into a single agent. It started with support the hardest surface a brand has and it expands from there: Shopping Agent Social Agent Siena working alongside a brands own operators. One agent across every surface with shared memory shared context and shared tools.

Hundreds of brands already run real customer volume on Siena in production. This is built working and growing and we are racing to build what comes next.

The team

We are a small fully distributed global team. We have built leverage into how we work which is what lets a team this size move at the speed we do.

We hire athletes. Everyone here owns real outcomes defaults to writing over meetings communicates with directness and acts the moment they see something worth acting on. Low ego high standards fast clock.

If you want to own real problems rather than close tickets keep reading.

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 theres a genuine product bug or infrastructure issue underneath not as a default path.

Youll work directly with the e-commerce brands running Sienas AI agents across complex integration environments. Youll 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 thats 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 Youll Do

Own technical resolution end-to-end

• You take full ownership of Tier 2 escalations. You diagnose and resolve without pulling in engineers unless theres 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. Youre 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 Sienas 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. Youre not just supporting AI products youre fluent in them.

Who You Are

Technical skills

• You have 1 year of technical support at a SaaS company. Youve 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.

• Youre fluent in customer-side JavaScript: browser devtools event handlers script conflicts timing issues. Youre 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.

• Youre 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.

• Youre 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

• Youre comfortable in ambiguity. You create structure where there isnt any.

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

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

• Youre 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.

• Youve 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.

• Youve 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.

• Youve shipped at least one systemic improvement project: auto-triage observability access or equivalent.

Nice to Have

• Youve 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.

• Youre familiar with modern observability tooling: Honeycomb Grafana Splunk Sentry Kibana or equivalents.

• Youve 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.

• Youre 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

• Real ownership. You will own problems not tasks with the autonomy to solve them your way and the trust to do it without a manager in your inbox.

• Work that ships and matters. What you build reaches real consumer brands fast.

• A category we are creating. The Agent of Record is new ground with unsolved problems and cutting-edge models not a crowded field to compete in.

• A team that respects your judgment. Globally distributed async-first low bureaucracy. We hire adults and treat you like one.

• Great salary plus equity or stock grants. Own a piece of what you build.

• Learning budget. If you are growing so are we.

• AI-fluency by default. Few places will push your work with production AI further or faster.

Our values

The people who thrive here are curious customer-obsessed and take ownership without being asked. They fix problems first and explain later. Theyre direct about feedbackboth giving and receiving itbecause 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 thats 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. Theyve 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 others AI workflows.

At Siena were not just looking for people who can do a job. Were looking for people who want to break boundaries create the future and reshape industries. If thats 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 .

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.

Required Experience:

IC