Senior Software Engineer II (Chicago)

Location

Austin, Chicago, DC, NYC

Employment Type

Full time

Location Type

Hybrid

Department

Engineering

Compensation

• $180K $210K

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:

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 its 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

This role is a good fit for you if:

• You arent 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.

Ideal Qualifications

• 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, BigQuery, 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 (from ideation and design to coding, testing, and release) 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 effectively across cross-functional teams to deliver outcomes.

Technology Stack

We dont require them all, but love those that have experience in or are interested in learning:

Python, Java, Snowflake, DBT, AWS (including API Gateway, Lambda, DynamoDB, Cloudwatch, EventBridge), and Github Actions. We also leverage numerous AI tools, including OpenAI, AWS Bedrock, and Github Copilot.

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.

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 Upsides in-office policy over time.

Compensation

The US base salary range for this full-time position is $180,000 - $210,000 + 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. 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 there's anything we can do to support a disability or special need during your application or interview process, please email [email protected] .

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.

Compensation Range: $180K - $210K