Senior Software Engineer II

Location

Austin, Chicago, DC, NYC

Full time

Hybrid

Engineering

• $170K – $210K

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.

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 are 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 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.

This role is a good fit for you if:

• 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, not only building robust solutions but also communicating their purpose, impact and rationale – so teams can 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.

• Proficiency in one or more modern programming languages, particularly Python or Java
• Proven experience in architecting, deploying and maintaining distributed systems on cloud platforms such as AWS, GCP, or Azure, including hands-on work with serverless and event-driven architectures.
• Fluency in modern SQL-based data platforms such as Snowflake, Databricks, Big Query, or Redshift.
• Hands-on experience working with Python-based orchestration tools like Airflow or Dagster to build scalable, reliable data workflows.
• A proven ability or desire to apply generative AI across the SDLC to boost velocity and quality.
• Strong communication skills; ability to clearly articulate technical concepts to both technical and non-technical audiences.
• Demonstrated ability to collaborate…