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 Upside
This is the first engineering hire on a new internal platform effort inside Upside's Revenue Operations organization. You'll be building a zero-to-one, AI-native system for our go-to-market teams; a substrate for agentic orchestration that is meant to take over the work our teams do today across cumbersome legacy tooling.
🎯 The Role
Reporting to the Sr. Director of Revenue Operations, you'll operate as a forward deployed engineer: embedded directly with the business, close to the people whose problems you're solving, and measured on outcomes rather than output. You'll sit with revenue teams, understand how they actually work, and build the systems that change it. You will define the architecture and technical direction of this platform.
✅ Key Responsibilities
Build the first version of an AI-native platform for Upside's go-to-market teams, working across agentic orchestration, automation, and the interfaces our revenue teams use every day
Embed with revenue teams to learn their workflows firsthand, then design and ship systems that meaningfully change how that work gets done
Own technical direction. You'll make the architecture calls, choose the tools, and set the patterns this platform grows on
Move from prototype to production quickly, then keep iterating as AI capabilities change underneath you
Anchoring your work to business outcomes. Success here is measured in what the platform unlocks for the business, not in tickets closed
Work with our security and infrastructure partners to make sure what you build is sound and supportable
Document decisions and tradeoffs clearly so the team that follows you can build on your work
📌 Required Qualifications
Staff-level engineering experience — roughly 8 years or comparable depth built through another path with a history of owning systems end to end
Experience taking something from zero to one: greenfield systems, early-stage products, or internal platforms you built from nothing
Real experience building with LLMs and AI APIs in production, including prompt design, output evaluation, and iterating toward reliability
Fluency with AI-assisted development tools as part of how you work, not as an experiment
Strong judgment about technical tradeoffs, and the ability to refactor and change direction as requirements shift
Genuine interest in the business side. You'll be spending time with revenue and operations teams, and curiosity about how they work is a real requirement of this role
The ability to work with a high degree of independence and ambiguity, and to bring stakeholders along as you go
Clear communication with both engineers and non-engineers
⭐ Desirable Experience
Understanding of CRM and revenue data models — Salesforce, HubSpot, or similar. Note that this role is about building what comes after those tools, not integrating deeply with them
Experience as an early or founding engineer at a startup, or as the person who built an internal tooling function
Familiarity with retrieval-augmented generation (RAG), vector databases, and embedding-based search
Experience in marketplace or high-growth environments
Experience with modern data platforms such as Snowflake
🎁 Benefits
Medical, dental, and vision coverage starting on Day 1
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 candid
