Senior CX Systems Engineer, AI & Automation

Meet Upside:

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retailprofit measurement attribution and incrementalityto provide users with more value on their everyday purchases and brick-and-mortar businesses with new profitable customers. Weve 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 youll build and maintain the systems integrations and AI-powered workflows that enable our support teams to operate efficiently while delivering exceptional customer experiences. Youll 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 Youll 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 Were Looking For

Required Qualifications

• 58 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 dont 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 Youll 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 youre excited about building systems that help people work smarter and deliver better customer experiences wed 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. Were 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 theres anything we can do to support a disability or special need during your application or interview process please email

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.

Required Experience:

Senior IC