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.

Role Overview

The Senior Systems & Technology Manager is responsible for the design, optimization, and evolution of the Consumer Operations technology stack. This role serves as the technical owner for key operational systems and integrations, with a strong mandate to identify, build, and scale AI-enabled solutions that improve customer experience and materially reduce operational costs.

This role operates at a highly autonomous level, partnering closely with Product and Engineering while remaining deeply embedded in Consumer Operations. Success requires strong technical depth, systems thinking, and the ability to translate operational pain points into scalable technical solutions.

Primary Focus Areas

Voice of the Customer (VOC) Reporting & Insights:

• Be a thought leader/owner in the development and maintenance of reporting that surfaces Voice of the Customer (VOC) insights across Consumer Operations channels.

• Build scalable, automated reports and dashboards that highlight customer sentiment, recurring issues, friction points, and experience trends.

• Partner with Consumer Operations, Product, and Marketing to ensure VOC insights are actionable and regularly incorporated into decision-making.

• Use data to connect customer feedback to operational drivers and improvement opportunities.

Systems Ownership & Integration:

• Own the operational effectiveness of core Consumer Operations systems, including Zendesk, Retool, Slack integrations, and related tooling.

• Ensure systems are stable, scalable, well-integrated, and optimized for frontline and back-office teams.

• Act as the technical point of accountability for system enhancements, integrations, and issue resolution.

• Proactively identify gaps or inefficiencies in the current tech stack and propose durable solutions.

AI & Automation Strategy:

• Research, evaluate, and build AI and automation opportunities to enhance the Consumer Operations technology stack.

• Partner directly with Product and Engineering to design and build AI-powered tools that:

  • Reduce Consumer Operations OpEx

  • Improve agent efficiency and response quality

  • Enable smarter routing, triage, and decision support

• Lead proof-of-concept development, pilots, and scaled rollouts of AI-enabled solutions.

• Ensure AI implementations meet standards for accuracy, security, customer trust, and regulatory compliance.
  

Required Qualifications:

• 8+ years of experience in a fast-paced, high-growth environment (fintech or similarly regulated industry preferred)

• Strong technical background with hands-on experience in:

  • SQL / MySQL

  • Python/Java or similar backend programming languages

• Demonstrated experience building operational reporting and dashboards to support Voice of the Customer (VOC) or customer experience initiatives

• Experience working with modern analytics and data platforms such as Snowflake, Hex, Looker, or similar tools

• Demonstrated experience working with AI and LLM-based systems, including:

  • Model integration and orchestration

  • AI-assisted workflows or automation

  • Evaluation of model performance and quality

• Experience designing and supporting complex system integrations

• Proven ability to work cross-functionally with Product, Engineering, and Operations

Location:

This hybrid role is based in our Austin, Chicago, DC, or NYC office. In-office attendance is required on Monday, Tuesday, and Thursday and may increase based on project-based needs and changes to Upside’s in-office policy over time.

Compensation:

The US base salary range for this full-time position is $130,000 - $150,000 + equity + benefits. The final starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. Your recruiter can share more about the specific salary range during the hiring process.

#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.