Head of Design and Research

Upside Services, Inc.

Job Overview

Location

Job Type

Full-time

Full Job Description

📋 Description

• As Head of Design and Research at Upside Services, Inc., you will lead a small, embedded team to elevate the consistency, polish, and craft of the consumer and payments experience, transforming the product from functional to flawless during a critical Phase II of scaling toward 10M MAU and billions in payments GMV.
• You will own quality and consistency across user journeys, lead and grow a team of designers and researchers, architect cohesive design systems, partner cross-functionally to embed design in discovery, deepen research integration into decision-making, and apply AI-native approaches to scale impact.
• You will join a mission-driven company that has already helped millions earn 2–3x more cashback and enabled hundreds of thousands of brick-and-mortar businesses to gain profitable customers, with billions in commerce flowing through its platform annually, directly benefiting retailers, consumers, and sustainability initiatives.
• In this role, you will sharpen your systems-level product thinking, scale design and research practices in a high-growth consumer environment, prove UX impact through data, and lead a team to achieve craft excellence while navigating ambiguity with bias to action.

🎯 Requirements

• Deep consumer product design experience in trust, credibility, and onboarding psychology driving conversion and retention, ideally in fintech, marketplaces, or transaction-driven products
• Track record designing habit-forming systems for frequency, retention, and cross-category adoption at consumer scale
• Personal experience scaling a consumer app from ~3M to 10M+ MAU during hypergrowth
• Strong systems-level product thinking with judgment on consistency vs. speed
• Comfort in analytical environments using data to drive and prove UX impact
• Experience leading design/research teams of 5–10 and raising individual craft
• AI-centric approach to design and research
• Bias to action; effective in ambiguity without needing perfect conditions

🏖️ Benefits

• Medical, dental, and vision coverage starting on Day 1
• Equity (ISOs)
• 401(k) program
• Family planning programs + paid parental leave
• Physical fitness and wellness memberships
• Emotional and mental health support programs
• Unlimited PTO + 10 paid federal holidays + annual week-long Winter Break
• Flexible work environment
• Lunch reimbursement for in-office employees
• Employee Resource Groups
• Learning and Development stipend
• Transparent culture
• Amazing mission

Skills & Technologies

Hybrid

$274k-289k

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Upside Services, Inc.

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About Upside Services, Inc.

Upside Services provides a cash-back platform that connects consumers with nearby fuel stations, grocery stores, and restaurants. The company earns revenue through performance-based marketing agreements with merchants, who pay only when Upside drives incremental profit above baseline sales. The mobile app delivers personalized offers and processes rebates to users’ bank accounts or digital wallets. Founded in Washington, D.C., Upside uses anonymized transaction data and machine-learning models to forecast demand and set dynamic incentives, aiming to increase foot traffic and basket size for partner businesses while rewarding consumer loyalty.

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