Head of Design & Research, Upside
$249-289k
Salary dependent on location. + Equity
More information about location
3 days a week in office
Mobile reward application for retail spending
Be an early applicant
Mobile reward application for retail spending
201-500 employees
Be an early applicant
$249-289k
Salary dependent on location. + Equity
More information about location
3 days a week in office
201-500 employees
Company mission
To advance the economic power of people living and working in the real world.
Role
Who you are
- Deep consumer product design experience where trust, credibility, and onboarding psychology drive conversion and retention — ideally fintech, marketplaces, or transaction-driven products
- Track record designing habit-forming systems (frequency, retention, cross-category adoption) at consumer scale
- Has personally helped scale a consumer app through hypergrowth (~3M → 10M+ MAU)
- Strong systems-level product thinking; sound judgment on where consistency matters vs. where to move fast
- Comfort in highly analytical environments; uses data to drive and prove UX impact
- Has led design/research teams of ~5–10 and raised individual craft
- AI-centric approach to design and research
- Bias to action; effective in ambiguity without requiring a perfect environment
What the job involves
- Upside is in Phase II — scaling toward 10M MAU, ~175K retail locations, and billions in payments GMV. Design & Research's mandate is narrow and clear: raise the consistency and polish bar across the entire consumer and payments experience, moving the product from "functional" to "flawless" and embedding design into early discovery
- This is a hands-on craft-and-scale leadership role for a small, embedded team. It is not a greenfield visionary role or a large-org-building role
- Own the quality, consistency, and polish bar across the consumer and payments experience
- Lead a small, tightly knit team of designers and researchers embedded in delivery pods; systematically grow their craft and how the team operates
- Architect cohesive design systems and frameworks across fragmented journeys and surfaces — balancing design integrity against iteration speed
- Partner with Product, Engineering, and Marketing to pull design into discovery and drive measurable outcomes across onboarding, discovery, redemption, and retention
- Deepen the research practice and its integration into decision-making
- Apply an AI-native approach to how design and research scale
Our take
Loyalty systems, vouchers, and other special offers have a proven track record at winning over new customers for businesses. However, customers can be reluctant to sign up due to the sheer number of these schemes. Upside exists to unify these loyalty schemes with a single flexible reward app.
While retail reward platforms are nothing new, Upside functions more like a marketplace, linking participating businesses to potential customers. It also rewards customers with cash back on eligible purchases, a more flexible reward than is traditional in loyalty schemes.
With over 50,000 businesses enrolled and 30 million app users, Upside has grown into a major player in this sector. The company is well-funded and ever-expanding its offering, with a product that is increasingly appreciated by consumers in an expensive world, as well as the businesses who depend on their custom.
Freddie
Company Specialist at Welcome to the Jungle
Insights
24% employee growth in 12 months
Company
Funding (1 round)
Apr 2022
$65m
SERIES D
Total funding: $65m
Company benefits
- Health and Wellness - We’re happy to provide our team members with generous health, vision, and dental insurance options
- Lunch - We cover the cost of lunch everyday for team members onsite to enhance our team building and encourage collaboration. Plus local restaurants appreciate it!
- Stock Options - Our team’s success is our company’s success, and we should all have a stake in that. We’re glad to offer our team members valuable stock options
- Unlimited PTO - Yes, you read that right. When you need time off, we’ve got you covered
Company HQ
Dupont Circle, Washington, DC
Leadership
Alex Kinnier
(CEO & Co-Founder)Experience as Group Product Manager for Google from 2005 to 2008. Senior Vice President of Products and Engineering for Opower from 2012 to 2015.
Wayne Lin
(CPO & Co-Founder)Experience as Product Manager for Google from 2005 to 2010. Vice President of Product Management & Analytics for Opower from 2010 to 2015.
Rick McPhee
(Co-Founder)Experience as Vice President of Engineering for HP's Fortify Software from 2008 to 2012. Senior Vice President of Engineering for Opower from 2012 to 2015.
Joanna Kochaniak
(Engineer & Co-Founder)Experience as Programmer Analyst for the Institute for Physical Sciences from 2007 to 2010. Lead Software Engineer for Opower from 2010 to 2015.
Jan Rubio
(Designer & Co-Founder)Experience as Research Assistant for George Washington University from 2009 to 2011. Senior Software Engineer for Opower from 2011 to 2016.
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