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

At Upside, engineers are expected to gather the right context from those around them and take thoughtful, calculated risks. By doing so, we help our teams move quickly and make informed decisions that lead to high quality software and delightful user experiences.

We're looking for engineers who are curious about the "why" behind what we build, and strive to understand the bigger picture so they can make better technical choices. We value individuals who seek out opportunities to improve our systems and deliver real business impact through their work. We embrace change and foster open conversations to help ideas evolve and grow.

Here are some ways we have seen engineers drive impact at Upside:

• Help cultivate a collaborative and safe environment. You can speak up to name problems, which will invite conversations that will then drive solutions.

• Learn and innovate on the ways we can improve our system. You are able to hone in on gaps in quality, security, performance, and speed of execution and generate buy-in to raise those bars.

• Partner deeply with cross functional teams. Whether it's aligning with marketing on experimentation, enabling better personalization with data science, or integrating feedback from designers, you are proactive in surfacing insights and turning them into technical action.

• Drive quality through documentation. You record your decisions, communicate tradeoffs, and ensure others can build upon your work.

• Set clear expectations on delivery. We all understand that plans change. You focus on setting an accurate and achievable goal from the start, and then keeping close alignment with key partners when milestones shift.

Why You Should Apply

Engineers come in many different shapes and sizes. This role is a good fit for you if:

• You put the customer at the center of every decision. You strive to build best in class consumer experiences, proactively surfacing friction in the journey and partnering with peers to remove it.

• You aren't afraid to challenge the status quo when it makes the team and business better. You learn from those around you while utilizing data to advocate for informed change.

• You thrive at the intersection of systems and storytelling. Whether creating helpful insights for merchants tracking their value on the platform, providing accurate billing or payments or ensuring the customer journey is well understood, you bring empathy for both merchants and consumers—and build solutions that empower others to experiment, iterate, and act confidently.

• You care about building resilient systems that scale. You bring a mindset of continuous improvement, and know when to invest in observability, automation, or new infrastructure to reduce toil and improve outcomes for the team and end users.

• You believe that pulling quality upstream starts with engineering. You champion best practices, encourage early testing and validation, and work closely with peers to build a culture of quality from the ground up.

Engineering Culture

We want our engineers to have the time and support to grow in their craft and contribute meaningfully to impactful technical decisions. Engineers are encouraged to focus deeply on their work, collaborate effectively with team members, and continuously develop their skills. Teams are thoughtfully staffed to create a dynamic and diverse environment that enhances learning and innovation.

Technology Stack

We don't require them all, but love those that have experience in or are interested in learning:

React, Typescript, JavaScript, Python, Snowflake, AWS (including API Gateway, Lambda, DynamoDB, Cloudwatch, EventBridge), Terraform, SQL/MySQL and Github Actions. We also leverage numerous AI tools, including OpenAI and Github Copilot.

Ideal Qualifications

• Guide, mentor and upskill the team to raise overall effectiveness and impact

• Drive experiences that deliver measurable business value

• Apply an analytical mindset to experiment, learn, iterate and grow

• Debug complex systems by interpreting data, forming hypotheses and making meaningful improvements

• Build with semantic HTML, CSS, and core JavaScript concepts

• Apply strong knowledge of core web and browser fundamentals (e.g., how a browser parses and constructs a web page)

• Write reliable automated tests as a foundation for quality

• Demonstrate a proven ability or strong desire to apply generative AI across the SDLC, from ideation and design to coding, testing and release, to increase velocity and quality

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 - $160,000 + 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.

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 View email address on click.appcast.io.

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.