Staff Forward Deployed Engineer, GTM Platform

About the role

As the first engineering hire for a new internal platform within Upside’s Revenue Operations, you’ll act as a forward‑deployed engineer embedded with go‑to‑market teams, building a zero‑to‑one AI‑native system that orchestrates and automates revenue workflows, defines the platform’s architecture, and delivers measurable business outcomes.

About the company

Upside transforms brick‑and‑mortar commerce by applying online‑retail technology—profit measurement, attribution, and incrementality—to give consumers higher cashback and help physical retailers acquire profitable customers. The platform handles billions of dollars in commerce annually, supports sustainability initiatives, and serves millions of users and hundreds of thousands of merchants.

Requirements

• ~8 years of staff-level engineering experience or comparable depth with end‑to‑end ownership of systems
• Proven experience taking zero‑to‑one greenfield systems, early‑stage products, or internal platforms from concept to production
• Hands‑on production experience building with LLMs and AI APIs, including prompt design, output evaluation, and reliability iteration
• Fluency with AI‑assisted development tools as part of regular workflow
• Strong technical judgment and ability to refactor or change direction as requirements shift
• Genuine interest in business operations; ability to work closely with revenue and operations teams
• Ability to work independently in ambiguous environments and bring stakeholders along
• Clear communication skills for both engineers and non‑engineers
• Language‑agnostic mindset; comfortable with React, TypeScript, Python or other stacks
• Understanding of CRM and revenue data models such as Salesforce or HubSpot (preferred)
• Experience as an early or founding engineer at a startup or building internal tooling functions (preferred)
• Familiarity with retrieval‑augmented generation (RAG), vector databases, and embedding‑based search (preferred)
• Experience in marketplace or high‑growth environments (preferred)
• Experience with modern data platforms such as Snowflake (preferred)