Upside Services, Inc. logo

Deputy General Counsel

Job Overview

Location

DC

Job Type

Full-time

Category

Product Management

Date Posted

May 21, 2026

Full Job Description

📋 Description

  • Oversee the entire company’s contract review and execution process, ensuring legal compliance and efficiency across all commercial agreements.
  • Draft, negotiate, and finalize commercial contracts with merchant partners, data providers, and third-party vendors, managing the full lifecycle from inception to execution.
  • Provide comprehensive legal advice across key areas including contract law, data privacy, data protection, consumer protection laws, and commercial litigation.
  • Collaborate with and manage relationships with outside counsel, coordinating strategy, billing, and deliverables to align with company objectives.
  • Develop, communicate, and monitor company-wide legal policies to ensure regulatory compliance and mitigate legal risk across operations.
  • Work closely with cross-functional teams including finance, product, engineering, and operations to provide timely and practical legal guidance on business initiatives.
  • Identify emerging legal risks in the technology and retail commerce space and proactively implement solutions to safeguard company interests.
  • Maintain rigorous attention to detail in all legal documentation, ensuring accuracy, consistency, and enforceability of agreements and policies.
  • Manage multiple legal projects simultaneously under tight deadlines while maintaining consistently high-quality work product in a fast-paced environment.
  • Serve as a trusted legal advisor to business leaders, translating complex legal concepts into actionable business recommendations.
  • Represent the company in legal matters requiring internal coordination and external advocacy, including disputes, regulatory inquiries, or compliance reviews.
  • Ensure all legal activities align with Upside’s mission of transforming brick-and-mortar commerce through technology-driven cashback and profit-sharing models.
  • Work from the company’s DC office on Mondays, Tuesdays, and Thursdays, with potential for increased in-office attendance based on project needs or policy changes.
  • Operate with significant autonomy, handling complex legal issues with minimal supervision while maintaining alignment with the CFO and broader legal team.
  • Maintain up-to-date knowledge of evolving federal and state regulations impacting data use, consumer transactions, and digital commerce platforms.
  • Contribute to a transparent, collaborative culture by fostering open communication and legal education across departments.
  • Support the growth of a small but expanding legal function by establishing scalable processes and documentation frameworks.

Skills & Technologies

Hybrid
$200k-220k

Ready to Apply?

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Upside Services, Inc. logo
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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