Articles about Upside

Featured Articles

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Taylor Rose Taylor Rose
Published on November 05, 2026

How Upside Engineers Build Mission-Driven Technology That Creates Value for Consumers and Businesses

Learn how Upside’s engineering team connects product development to the company mission. 

Built In Staff, With AI Built In Staff, With AI
Updated on October 29, 2026

21 Top Companies Hiring Developers in Chicago

From global e-commerce giants to high-frequency trading firms, these companies are recruiting developers to build the next generation of enterprise software and industrial technology.

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Alyssa Schroer Alyssa Schroer
Updated on October 27, 2026

109 Chicago Software Companies You Should Know

These are the top software companies that are helping make Chicago a thriving hub for tech.

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Built In Staff Built In Staff
Updated on April 08, 2025

9 Chicago Companies Hiring This Fall

The fourth quarter of 2023 is no time for a hiring slowdown at these Chicago area companies.

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Author Unknown
Updated on December 02, 2025

Upside Company Culture: How the Company Transforms Everyday Purchases into Greater Change

The Washington D.C.-headquartered company has driven $300 million in savings for users and $650 million in profit for merchants since its founding in 2016, all while committing 1 percent of its revenue to sustainability initiatives.

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Abel Rodriguez Abel Rodriguez
Updated on October 29, 2026

38 Top Fintech Companies in Chicago to Know

With Chicago's history as a central trading and banking city, the biggest institutions have inspired a generation of talented, tech-minded financial professionals to build startups that use tech to solve the industry's biggest problems.

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Matthew Urwin Matthew Urwin
Updated on October 09, 2026

73 Major Companies in Chicago to Know

Check out this list of the top companies making Chicago a vibrant tech hub.

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Alyssa Schroer Alyssa Schroer
Updated on October 22, 2026

93 Companies in Downtown Chicago You Should Know

Downtown Chicago is home to some of the world’s top tech companies. Here are a few.

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Recently posted jobs

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Artificial Intelligence • Fintech • Machine Learning • Mobile • Payments • Retail • Software
Own the strategy, roadmap, and growth of Upside’s restaurant vertical. Adapt incrementality measurement and offer optimization to restaurant economics, build merchant-facing reporting and onboarding products, and drive partner adoption, retention, and profitability. Partner with engineering, data science, design, sales, account management, and marketing while making integration decisions across POS, payments, and data systems. Establish OKRs and lead a 0-to-1 business area without direct authority.
One Month AgoSaved
Hybrid
4 Locations
Artificial Intelligence • Fintech • Machine Learning • Mobile • Payments • Retail • Software
Leads the Merchant & Pay engineering organization, overseeing managers and teams responsible for merchant, partner, payment, and internal tooling systems. Owns technical strategy, multi-year roadmaps, reliability, scalability, security, engineering standards, and generative AI adoption. Partners with Product, Data, Security, and company leadership while recruiting, developing, and retaining engineering talent. Requires extensive engineering leadership experience, AWS expertise, marketplace or payments experience, and experience scaling business-critical platforms.
One Month AgoSaved
Hybrid
4 Locations
Artificial Intelligence • Fintech • Machine Learning • Mobile • Payments • Retail • Software
Lead a full-stack Reconciliation team owning transaction-matching pipelines across mobile and backend systems. Drive reliability, observability, and accuracy for post-claim flows, coach and grow engineers, contribute hands-on in high-leverage technical areas, partner cross-functionally, and scale systems and processes to improve transaction success and user trust.