Siena
AI
TechnicalSupportEngineer
Neural analysis suggests this role is
optimal for Entry candidates.
“Technical Support Engineer at Siena. Skills: Technical Support, API Debugging, JavaScript Debugging, AI Agent Behavior. Own technical resolution end-to-end. Take full ownership of Tier 2+ escalations”
What You'll Achieve.
Engineers are no longer pulled into support escalations; Tier 2+ resolution time baseline is established; Mapped the most common technical failure patterns; Tier 2 pattern has moved back to Tier 1; Resolution time is measurably improving; CSAT on technical issues is improving; Engineering is fully protected from support interruptions; Feedback loop to Engineering is running systematically; Support team is resolving more independently; Shipped at least one systemic improvement project
Industry & Context.
Diagnose; Resolve; Debug; Triage; Problem-solving; Analytical skills
Available to cover North America timezones
What They're Looking For.
Must Have
1+ year of technical support at a SaaS company, Owned hard technical threads end-to-end, Debug REST APIs, Debug webhooks, Debug auth flows, Debug JSON, Debug HTTP protocols, Fluent in customer-side JavaScript, Browser devtools, Event handlers, Script conflicts, Timing issues, Write diagnostic SQL, Comfortable with production systems, Logs analysis, Monitoring tools, System debugging, Strong written and verbal English, Build trust quickly, Empathy and urgency coexist, Work independently in a remote environment, Async communication, Comfortable in ambiguity, Create structure where there isn’t any, Leverage mindset is already a habit, Coached or trained non-technical teammates, Available to cover North America timezones
Nice to Have
Experience with LLMs, Prompt engineering, AI model integration, Triage AI agent behavior, Distinguish prompt/config issue from model-level problem, Familiar with how LLM-based systems fail, Experience with AI APIs, Supported AI or LLM-based products before, Background in e-commerce or DTC, Familiar with modern observability tooling, Built internal tooling or automation, Fluent with Claude Code or equivalent AI coding tools
What You'll Do.
Own technical resolution end-to-end
Take full ownership of Tier 2+ escalations
Diagnose and resolve without pulling engineers
Debug API integrations independently
Diagnose and resolve customer-side JavaScript issues
Triage AI and chatbot behavior
Run diagnostic SQL on data discrepancies
Work Tier 1 tickets alongside Support team
Move patterns back to Tier 1
Build and maintain internal documentation
Scope and drive systemic improvements
Own the customer-facing experience
Own complex technical issues directly with customers
Translate complex technical problems
Manage expectations confidently
Escalate to Engineering only when required
Support customers integrating with Siena’s AI agents
Troubleshoot LLM-based agent behavior
Troubleshoot integration edge cases
Troubleshoot platform failures
Use AI tools actively in diagnostic workflow
How You'll Work.
Team & Collaboration
Collaborate with Engineering on issues; Work with product team; Work alongside the Support team; Build a working partnership with Support Manager; Share knowledge about AI workflows
Communication Scope
Strong written and verbal English; Explain complex technical issues; Translate complex technical problems into clear explanations
Process & Methodology
Scope and drive systemic improvements, Drive systemic improvements
Full Job Description
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
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