Senior Regulatory Counsel

Sorry, this job was removed at 12:07 a.m. (CST) on Thursday, Jul 10, 2025
Easy Apply
Chicago, IL, USA
Hybrid
Fintech • Financial Services
Our people make us exceptional.
The Role

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.

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.

Required Skills and Experience:

  • J.D. from an accredited law school and admission to a state bar
  • 6+ years of legal experience with a focus on financial laws and regulations
  • Experience analyzing legal and regulatory issues relating to cryptoassets
  • 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
  • Must be comfortable working independently in a fast-paced environment
  • Ability to effectively communicate at all levels of the firm and across all functional group

The annual base salary range for this position is $200,000 to $300,000, 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 https://drw.com/privacy-notice.

California residents, please review the California Privacy Notice for information about certain legal rights at https://drw.com/california-privacy-notice.

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DRW Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about DRW and has not been reviewed or approved by DRW.

  • Career-Linked Recognition & Rewards Pay is considered competitive to strong in revenue-adjacent roles, with substantial cash components that reward performance. Feedback suggests totals can be compelling when teams and markets perform well.
  • Wellbeing & Lifestyle Benefits Day-to-day perks such as daily catered meals, wellness offerings, and on-site amenities are consistently highlighted. These office-centric benefits enhance the overall value of the package, especially in major hubs.
  • Healthcare Strength Core medical, dental, and vision coverage is described as comprehensive with broad networks under common plan options. Feedback suggests health coverage is a solid pillar of the total rewards.

DRW Insights

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The Company
HQ: Chicago, IL
1,825 Employees
Year Founded: 1992

What We Do

A diversified trading firm that utilizes our own capital and trades at our own risk. We bring sophisticated technology and exceptional people together to solve complex problems in markets around the world and across many asset classes. We are motivated to compete at the highest level and commit to operate with respect, curiosity and an open mind.

Why Work With Us

The DRW approach is simple: tenure, experience and titles don’t matter as much as ideas, execution and results. We believe in creating opportunity to take on more complex problems, more interesting projects and more specialized skills. It’s a results-driven environment where friendships grow and respect is the norm.

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