Stay AI

Senior Technical Support Lead

Stay AI

full-time

Posted on:

Location Type: Remote

Location: Remote • 🇺🇸 United States

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Job Level

Senior

Tech Stack

CloudSQL

About the role

  • Serve as the highest-tier technical escalation point for complex, cross-system, and high-impact customer issues.
  • Diagnose and resolve issues involving APIs, integrations, webhooks, data pipelines, authentication, and platform configuration.
  • Perform deep technical investigations using logs, monitoring tools, databases, and internal debugging environments.
  • Lead the technical response during major incidents, coordinating with Engineering, Product, and Support stakeholders.
  • Drive root-cause analysis and post-incident reviews, documenting findings and ensuring preventive actions are implemented.
  • Maintain ownership of long-running or multi-team technical issues until full resolution.
  • Develop, refine, and enforce best practices for troubleshooting, escalation, and customer communication.
  • Identify recurring product issues or operational gaps and proactively propose solutions.
  • Contribute to internal runbooks, knowledge base articles, and tooling improvements to streamline support workflows.
  • Act as a bridge between Support and Engineering/Product teams, translating customer issues into actionable technical insights.
  • Provide feedback on product reliability, edge-case behaviors, and customer experience pain points.
  • Participate in technical reviews for new features to ensure support readiness and identify potential risk areas.
  • Manage high-stakes customer interactions that require deep technical understanding and clear communication.
  • Assist customers with advanced debugging, configuration best practices, API usage, and integration flows.

Requirements

  • 5–7+ years of experience in technical support, technical operations, or product support roles in a SaaS or cloud environment.
  • Expert troubleshooting skills across Shopify solutions with a focus on subscriptions
  • Ability to break down complex technical problems and communicate findings clearly to both technical and non-technical audiences.
  • Experience working directly with engineering teams on bug triage, debugging, and release readiness.
  • Nice-to-Haves
  • Strong familiarity with tools such as Postman, cURL, SQL, logging/monitoring systems, and debugging utilities.
  • Familiarity with incident management frameworks (e.g., ITIL, post-mortems, RCA methodology).
  • Background supporting products with APIs, integrations, or data pipelines.
  • Prior experience in a customer-facing senior escalation or technical lead role.
Benefits
  • Collaboration is at the heart of everything we do, as we firmly believe in the power of teamwork.
  • We try to create opportunities to meet each other, organizing annual offsite retreats in beautiful Park City and Mexico!

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
APIintegrationswebhooksdata pipelinesauthenticationtroubleshootingdebuggingSQLincident managementroot-cause analysis
Soft skills
communicationproblem-solvingleadershipcollaborationcustomer serviceanalytical thinkingdocumentationproactive approachtechnical translationstakeholder management