Full-Stack 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 Full-Stack 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 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

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

Why You’ll Love This Role

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