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.

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.

• 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.

• 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.

• 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.

• 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.

• 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.

We don’t expect experience with every technology listed below, but familiarity with several is helpful:

• Python

• JavaScript / TypeScript

• SQL / MySQL

• React

• AWS (Lambda, API Gateway, DynamoDB, EventBridge, CloudWatch)

• Snowflake

• Zendesk

• Retool

• Terraform

• GitHub Actions

• OpenAI, Claude, and other AI platforms

• Build practical AI solutions that solve real customer and business problems.

• Own meaningful projects with measurable impact on customer experience and operational efficiency.

• Work at the intersection of software engineering, automation, and applied AI.

• Partner closely with Operations, Product, and Engineering teams.

• Help shape how Upside scales customer support through technology and innovation.

At Upside, we value curiosity, ownership, collaboration, and continuous improvement. If you’re excited about building systems that help people work smarter and deliver better customer experiences, we’d love to hear from you.

#LI-Hybrid

#LI-NE1

Benefits:

• Medical, dental, and vision coverage starting on Day 1

• Equity (ISOs)

• 401(k) program

• Family planning programs + paid parental leave

• Physical fitness and wellness memberships

• Emotional and mental health support programs

• Unlimited PTO + 10 paid federal holidays + our annual, week-long Winter Break

• Flexible work environment

• Lunch reimbursement for in-office employees

• Employee Resource Groups

• Learning and Development stipend

• Transparent culture

• Amazing mission!

Diversity and Inclusion:

Diversity drives innovation, and our differences make us stronger. We‘re passionate about building a workplace that represents a variety of backgrounds, skills, and perspectives, and we do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Everyone is welcome here!

If there's anything we can do to support a disability or special need during your application or interview process, please email [email protected].

This email is for accessibility accommodations only, it should not be used to submit job applications.

Notice To Recruiters And Placement Agencies:

This is an in-house search with a dedicated recruiter. Please do not submit resumes to any person or email address at Upside. Upside is not liable for, and will not pay, placement fees for candidates submitted by any party or agency other than its approved recruitment partners.