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UpsideUpsideAustin, TX

Senior CX Systems Engineer, AI & Automation

Build and maintain AI-powered workflows, backend services, and integrations to automate customer support operations using Python, JavaScript/TypeScript, SQL, and LLM platforms like OpenAI and Claude.

130k – 150k
Hybrid5+ YOESupport Engineering

About the role

What You’ll Do

Build AI-Powered Customer Operations Solutions

  • Design, develop, and maintain AI-powered workflows that improve customer support operations and customer experience.
  • Leverage LLM platforms such as OpenAI, Claude, and similar technologies to automate repetitive tasks and enhance agent productivity.
  • Improve chatbot experiences through workflow automation, knowledge integration, and operational tooling.
  • Partner with Consumer Operations stakeholders to identify opportunities where AI can reduce manual effort and improve service quality.
  • Measure and iterate on AI solutions using operational data, customer feedback, and performance metrics.

Develop Systems and Integrations

  • Build and maintain integrations across systems such as Zendesk, Retool, Slack, and internal platforms.
  • Develop backend services, APIs, and automation workflows using Python, SQL, and JavaScript/TypeScript.
  • Identify operational bottlenecks and build scalable solutions that eliminate repetitive work.
  • Ensure systems are reliable, maintainable, and well-documented.
  • Troubleshoot production issues and continuously improve operational tooling.

Deliver Insights Through Data

  • Build reporting and dashboards that help teams understand customer experience trends and operational performance.
  • Analyze support interactions and customer feedback to identify opportunities for process improvement.
  • Partner with Operations and Product teams to turn customer insights into actionable improvements.
  • Use data to evaluate the effectiveness of automation initiatives and support investments.

What We’re Looking For

Required Qualifications

  • 5–8 years of software engineering experience in a fast-paced technology environment.
  • Strong proficiency in Python.
  • Strong proficiency in JavaScript or TypeScript.
  • Experience building backend services, APIs, integrations, and automation workflows.
  • Hands-on experience working with LLM platforms such as OpenAI, Claude, or similar AI technologies.
  • Experience building, improving, or supporting chatbot and AI-assisted workflow solutions.
  • Strong SQL skills and experience working with operational or analytical data.
  • Experience integrating third-party platforms using APIs and webhooks.
  • Ability to work effectively with Operations, Product, and Engineering stakeholders.
  • Strong problem-solving skills with a practical, business-oriented mindset.

Preferred Qualifications

  • Experience with Zendesk, Retool, or similar customer operations platforms.
  • Experience with Snowflake, Hex, Looker, or other analytics tools.
  • Experience working in fintech, marketplaces, SaaS, or other high-growth environments.
  • Experience with AWS services and serverless architectures.
  • Familiarity with prompt engineering, LLM evaluation, and AI workflow optimization.
  • Experience building internal tools that improve operational efficiency.

Technology Stack

Python, JavaScript/TypeScript, SQL/MySQL, React, AWS (Lambda, API Gateway, DynamoDB, EventBridge, CloudWatch), Snowflake, Zendesk, Retool, Terraform, GitHub Actions, OpenAI, Claude.

Skills

PythonJavaScriptTypeScriptSQLOpenAIClaudeLLMsZendeskRetoolAWS
Upside

Senior CX Systems Engineer, AI & Automation

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Build and maintain AI-powered workflows, systems integrations, and automation using Python, JavaScript/TypeScript, and SQL to improve customer support operations and tooling.

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