Meet UpsideWe 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 RoleUpside is building a new generation of internal platforms that help our go-to-market teams operate more efficiently and make better decisions. In this role, you will design and build AI-native systems that improve how revenue teams manage pipeline, analyze performance, and automate operational workflows.Reporting to the Sr. Director of Revenue Operations, you will work at the intersection of engineering, AI, and business operations, building systems that support how Upside acquires merchants, serves partners, and scales its go-to-market motion.
You will help define the architecture and technical direction of these platforms as they evolve.This role is a strong fit for engineers who are curious about how GTM teams operate and enjoy translating business workflows into reliable, well-designed software systems. The ideal candidate has fully embraced and applied modern AI tools and automation to real operational challenges and enjoys owning systems end-to-end.What You'll DoBuild high-impact applications and tools that accelerate Upside's go-to-market motion. Develop AI-native tools that help revenue teams manage pipeline, analyze performance, and automate operational workflowsPartner deeply with cross-functional teams to understand business workflows and translate them into scalable technical solutions. Prototype, iterate, ship and maintainOwn systems end-to-end. Design across the stack from front-end interfaces to backend services, automation pipelines, and AI orchestration layersContinuously improve the systems you build. Identify opportunities to increase reliability, performance, and scalability while reducing manual work for the teams that rely on these toolsStrong understanding of prompt design and prompt engineering as a core part of building AI-powered systems, including structuring prompts, evaluating outputs, and iterating on prompt strategies to improve reliability and qualityDrive quality through clear communication and documentation.
Record design decisions, communicate tradeoffs, and ensure others can build upon your workDeliver reliably and transparently. Set clear expectations, communicate progress, and keep stakeholders aligned as priorities evolveWhat We're Looking For8+ years of professional software engineering experience, with demonstrated depth in full-stack development (React/TypeScript plus backend/database experience)Deep experience using AI-assisted development tools to improve engineering velocity and qualityExperience building applications or systems that leverage LLMs, AI APIs, or modern AI frameworksExperience designing and owning internal platforms or operational systems end-to-endFamiliarity with modern deployment and infrastructure platforms (such as Supabase, Vercel, or similar environments)Strong product intuition and the ability to translate business workflows into well-architected technical solutionsTrack record of leading projects, mentoring teammates, and delivering measurable outcomesStrong communication skills and the ability to collaborate effectively with both technical and non-technical stakeholdersNice to HaveExperience working with CRM systems or revenue platforms (Salesforce, HubSpot, or similar)Experience in marketplace or high growth-stage SaaS environmentsFamiliarity with retrieval-augmented generation (RAG), vector databases, and embedding-based searchExperience working with modern data platforms such as SnowflakeTechnology StackWe don't require experience with all of these technologies, but we're excited to work with engineers who have experience in or are interested in learning: React, TypeScript, Next.js, Python (FastAPI), PostgreSQL, Supabase, Vercel, and modern API-driven architectures. We also leverage numerous AI tools across our development workflow, including OpenAI and GitHub Copilot.LocationThis 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.CompensationThe US base salary range for this full-time position is $214,000 - $245,000 + 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.BenefitsMedical, dental, and vision coverage starting on Day 1Equity (ISOs)401(k) programFamily planning programs + paid parental leavePhysical fitness and wellness membershipsEmotional and mental health support programsUnlimited PTO + 10 paid federal holidays + our annual, week-long Winter BreakFlexible work environmentLunch reimbursement for in-office employeesEmployee Resource GroupsLearning and Development stipendTransparent cultureAmazing mission!Diversity and InclusionDiversity 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 is for accessibility accommodations only, it should not be used to submit job applications.Notice To Recruiters And Placement AgenciesThis 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.