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Staff Forward Deployed Engineer, GTM Platform

Upside · NYC · Remote

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About Upside

Earn every time you shop gas, grocery, or food with Upside's free top-rated app. Get cash back on everyday necessities, making your purchases more rewarding. Download and start earning today! Backed by Bessemer and General Catalyst.

About the role

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.

What they're looking for

  • 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
More about this role

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.

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.

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...

Read the full posting on Upside's site ↗

GTM Strategy & Operations

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