Senior CX Systems Engineer, AI & Automation

Meet Upside: We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail—profit measurement, attribution, and incrementality—to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We’ve helped millions of users earn 2 to 3 times more cashback than any other product, and hundreds of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives. ABOUT THE ROLE We are looking for a Senior CX Systems Engineer, AI & Automation to help scale the technology that powers our Consumer Operations organization. In this role, you’ll build and maintain the systems, integrations, and AI-powered workflows that enable our support teams to operate efficiently while delivering exceptional customer experiences. You’ll work closely with Consumer Operations, Product, and Engineering partners to automate manual processes, improve support tooling, and leverage AI technologies to solve real business problems. This is a highly hands-on engineering role focused on execution, experimentation, and continuous improvement. The ideal candidate enjoys building practical solutions, working across systems, and using emerging AI technologies to drive measurable impact. 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 (Proficient), Strong 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 platfo