Job Description
Meet Upside:
We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail—profit measurement attribution and incrementality—to provide users with more value on their everyday purchases and brick-and-mortar businesses with new profitable customers. We’ve helped millions of users earn 2 to 3 times more cashback than any other product and hundreds of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year and that value goes directly back to our retailer partners the consumers they serve and important sustainability initiatives.
The Impact You'll Make:
Upside is seeking an experienced attorney to serve as Deputy General Counsel. The Deputy General Counsel will report to the CFO to identify develop communicate and monitor policies that will ensure compliance with law by the entire company. This is a great opportunity to join a small but growing legal team and to work on novel issues in an exciting fast-paced environment!
What you’ll do:
Oversee contract review and execution process for entire company
Draft and negotiate commercial contracts with merchant partners data providers and vendors
Provide legal advice across many subject areas including contract law privacy data protection consumer protection laws and commercial litigation
Work with and manage outside counsel
Competencies You'll Need:
12+ years of experience as a practicing attorney (including in house or at a law firm)
Extensive experience and expertise with drafting and negotiating commercial contracts
Experience with data privacy law is preferable
Ability to handle major problems in practice areas with little or no supervision
Sound business judgment and industry knowledge
Experience managing client relationships with business leaders
Experience in the technology industry is highly preferred
Ability to manage multiple projects and meet deadlines with consistently high-quality work product in a fast-paced environment
Strong interpersonal skills with ability to interact effectively and work collaboratively with individuals at all levels
High attention to detail with strong organizational skills and ability to work independently
J.D. degree and membership in at least one US state bar
Location:
This hybrid role is based in our DC office. In-office attendance is required on Monday Tuesday and Thursday and may increase based on project-based needs and changes to Upside’s in-office policy over time.
Compensation:
The U.S. base salary range for this full-time position is $200000 - $220000 + equity + benefits. The final starting pay will be determined based on job-related skills experience qualifications work location and market conditions. Your recruiter can share more about the specific salary range during the hiring process.
#LI-Hybrid
#LI-CO1
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 + our 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!
Diversity and Inclusion:
Diversity drives innovation and our differences make us stronger. We‘re passionate about building a workplace that represents a variety of backgrounds skills and perspectives and we do not discriminate based on race religion color national origin gender sexual orientation age marital status veteran status or disability status. Everyone is welcome here!
If there's anything we can do to support a disability or special need during your application or interview process please email [email protected].
This email is for accessibility accommodations only it should not be used to submit job applications.
Notice To Recruiters And Placement Agencies:
This is an in-house search with a dedicated recruiter. Please do not submit resumes to any person or email address at Upside. Upside is not liable for and will not pay placement fees for candidates submitted by any party or agency other than its approved recruitment partners.
Skills Required
- 12+ years of experience as a practicing attorney
- Extensive experience in drafting and negotiating commercial contracts
- Experience with data privacy law
- J.D. degree and membership in a US state bar
What the Team is Saying




Upside Compensation & Benefits Highlights
- Healthcare Strength—Comprehensive medical coverage and mental-health programs are highlighted with dental and vision included. Additional offerings such as abortion‑travel support and wellness resources broaden the health safety net.
- Parental & Family Support—Generous parental leave for all new parents is emphasized alongside adoption assistance childcare benefits and a partnership with Carrot Fertility. These elements signal robust support for family‑forming and caregiving needs.
- Leave & Time Off Breadth—An unlimited PTO policy and paid time off (including holidays and sick days) are consistently featured. Flexible and hybrid/remote work options further support time away when needed.
Upside Insights
What We Do
Upside is a technology company that increases the financial power of people and businesses in the real world. Our technology has helped millions of people get more purchasing power on the things they need and tens of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year and that value goes directly back to our retailers the consumers they serve and towards important sustainability initiatives.
Why Work With Us
We proactively apply our company values in everything we do so that we develop thoughtful leaders create inclusive spaces and develop creative solutions for our communities inside and outside the office.
Gallery
Upside Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
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Date Posted
05/19/2026
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