# Senior CX Systems Engineer, AI & Automation

**Company:** [Upside](https://hotfix.jobs/companies/upside)
**Location:** Austin, TX, Washington, DC, New York, NY
**Role:** Support Engineering
**Salary:** $130k – $150k/yr
**Experience:** 5+ years
**Skills:** Python, JavaScript, TypeScript, SQL, OpenAI, Claude, LLMs, Zendesk, Retool, AWS
**Posted:** 2026-06-03

> 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.

## Job Description

## 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.

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