Software Engineer II

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. I thought it would be helpful to highlight what I’m looking for on my team. This role is a good fit for you if:

• You enjoy working at the intersection of engineering and enablement. You’ll be the bridge between our external partners and Upside’s internal systems, helping to ensure integrations are smooth, scalable, and reliable.

• You thrive on variety. Some days you’ll be deep in code optimizing partner-facing APIs, and other days you’ll be troubleshooting an integration or shaping reusable tooling to accelerate partner onboarding.

• You value collaboration. You’ll work closely with internal product and platform teams, as well as directly with external technical stakeholders, to solve real business problems with clean, pragmatic engineering.

• You care about quality and clarity. Whether it’s writing resilient Python services, improving observability, or documenting integration flows, you take pride in building solutions that others can easily extend and rely on.

• You care about ownership: You enjoy owning technical relationships through different stages in the partner lifecycle: Vetting, Launching, Growing, and Maintaining.

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:
Python (primary), Java (partner APIs and internal services). Other areas of our engineering stack include AWS (API Gateway, Lambda, DynamoDB, EventBridge, CloudWatch), Snowflake, DBT, logging/metrics tooling, and GitHub Actions. We also leverage numerous AI tools, including OpenAI, AWS Bedrock, and GitHub Copilot.

Ideal qualifications:

• Innate curiosity for improving quality, scalability, and observability

• Passionate about building resilient partner-facing systems that drive measurable business value

• Analytical mindset with a knack for experimenting, learning, iterating, and growing

• Foundational debugging skills to investigate data, build hypotheses, and make meaningful improvements

• A desire to apply generative AI across the SDLC (from ideation and design to coding, testing, and release) to boost 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 $120,000 - $145,000 + 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 [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.