Upside operates a two-sided marketplace connecting consumers and physical retailers through a rewards mechanism. The tech stack—Snowflake, dbt, Dagster, Looker, Tableau—reflects a data-driven company; they're adopting Snowflake Cortex for AI workloads while actively hiring senior engineers and data practitioners (52 of 91 open roles), suggesting heavy investment in platform reliability and marketplace optimization. Active projects around merchant enablement, partner integration, and AI-native revenue pipelines indicate a shift from consumer acquisition toward B2B partnership scaling.
Notable leadership hires: Retailer & Channel Partnerships Director, Channel Partnerships Director, Retailer Partnerships Director
Upside is a fintech and retail-tech company that operates a cashback and rewards platform designed to increase purchasing power for consumers while driving measurable profit for brick-and-mortar merchants. The business model is two-sided: consumers earn rewards on in-store purchases; merchants gain customer acquisition and loyalty data. Founded in 2016, the company serves millions of consumers and tens of thousands of physical retailers across the United States. Operations are headquartered in Washington, D.C., with a team of 201–500 employees. Current focus areas include expanding merchant acquisition, optimizing the two-sided marketplace mechanics, and building integration tooling to onboard retail partners at scale.
Upside runs on AWS (Lambda, DynamoDB, SNS, SQS, Control Tower), Snowflake for data warehousing, dbt for transformation, Dagster for orchestration, and Looker/Tableau for analytics. For merchant and partnership integrations, they use DocuSign, Conga, Ramp, and Outreach.
Current priorities include merchant acquisition strategy, merchant enablement for pay and marketplace products, partner integration and onboarding tooling, and AI-native systems for revenue pipeline management.
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