Senior Regulatory Counsel

Drw
Chicago, IL
DRW is a diversified trading firm with over 3 decades of experience bringing sophisticated technology and exceptional people together to operate in markets around the world. We value autonomy and the ability to quickly pivot to capture opportunities, so we operate using our own capital and trading at our own risk. Cumberland - a DRW Company , is the cryptoasset arm of DRW, established in 2014 after pursuing an early interest in cryptoassets and their underlying technologies. Today, Cumberland is a global leader in cryptoassets, uniquely positioned between the traditional financial markets and the cryptoasset ecosystem. From our offices in Chicago, London and Singapore, Cumberland provides 24-hour access to a wide array of cryptoassets while helping the crypto ecosystem evolve in a responsible, sustainable way.

We are currently seeking a Senior Regulatory Counsel to join our global legal team and work on a wide variety of regulatory and strategic matters. This role will be located in either Chicago or Washington D.C. Candidates from other U.S. locations may also be considered, depending on experience.

Core Duties:
  • Regulatory Counsel : Provide practical, risk-weighted legal and regulatory advice to the Cumberland team in connection with new business opportunities and day-to-day operations.
  • Strategic Direction : Provide thought leadership and strategic direction on innovative Cumberland initiatives, including on-exchange and over-the-counter trading, venture capital investments and strategic partnerships. Work directly with Cumberland’s executive team to structure and develop cutting-edge opportunities in the crypto space.
  • Project Execution : Collaborate across functional groups within Cumberland and DRW globally to drive strategic objectives, including internal legal colleagues, outside counsel, tax, HR, accounting, treasury and trading operations.
  • Regulatory Engagement: Monitor legislative and regulatory developments impacting Cumberland's business and collaborate with internal stakeholders to develop positions and, where necessary, engage with industry groups, policymakers, and regulators with respect to such positions.
Required Skills and Experience:
  • J.D. from an accredited law school and admission to a state bar
  • 5-10 years of legal experience with a focus on financial laws and regulations, particularly SEC and CFTC
  • Experience analyzing legal and regulatory issues relating to both cryptoassets and “TradFi” products
  • Understanding of U.S. regulatory regimes applicable to cryptoasset trading (SEC, CFTC, NYDFS, AML)
  • Some experience with non-U.S. cryptoasset regulatory matters is a plus
  • Experience with and interest in crypto and TradFi policy is also a plus (e.g., SEC and CFTC rulemakings, comment letters, policy advocacy, market structure issues, etc.)
  • Must be comfortable working independently in a fast-paced environment
  • Ability to effectively collaborate with diverse stakeholders and communicate at all levels of the firm and across all functional groups
The annual base salary range for this position is $150,000 to $275,000 depending on the candidate’s experience, qualifications, and relevant skill set. The position is also eligible for an annual discretionary bonus. In addition, DRW offers a comprehensive suite of employee benefits including group medical, pharmacy, dental and vision insurance, 401k (with discretionary employer match), short and long-term disability, life and AD&D insurance, health savings accounts, and flexible spending accounts. For more information about DRW's processing activities and our use of job applicants' data, please view our Privacy Notice at []( . California residents, please review the California Privacy Notice for information about certain legal rights at []( . #LI-DW1
Posted 2026-06-06

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