Position Summary:

Grayscale Investments is seeking a Chief Compliance Officer to lead and own the compliance program across its Registered Investment Adviser, Broker-Dealer, registered fund complex, and overall product strategies, including active and on-chain. Reporting to the Chief Legal Officer, the CCO is the firm’s senior compliance authority, responsible for designing, implementing, and continuously improving a compliance infrastructure that is rigorous, scalable, and commercially minded.

The ideal candidate brings deep regulatory expertise, a hands-on management style, and a genuine orientation toward enabling business growth within appropriate guardrails. This is a builder role: the CCO will hire, develop, and lead a growing compliance team while serving as a trusted partner to business stakeholders across the firm.

Responsibilities:

• Design, implement, and maintain a comprehensive compliance program covering RIA, B/D, and 40 Act registered fund obligations, including all policies, procedures, testing, and supervisory controls.
• Monitor proposed SEC, FINRA, NFA, and CFTC rulemaking on an ongoing basis and translate regulatory developments into timely, actionable policy updates and business guidance.
• Assess compliance risk for all new products, funds, vehicles, and business lines prior to launch, delivering clear risk assessments and recommended controls to the CLO and relevant business leads.
• Oversee the marketing compliance and vendor due diligence programs, setting standards and maintaining accountability for outcomes while empowering team members to lead day-to-day execution.
• Serve as primary point of contact for the SEC, FINRA, and NFA, managing all examination logistics, document productions, and regulator communications from initial request through examination close.
• Maintain the regulatory relationships proactively, anticipating exam risk, ensuring audit-ready documentation at all times, and keeping the CLO apprised of open matters and remediation status.
• Build and sustain a firm-wide culture of compliance, serving as an accessible, practical resource for colleagues at all levels and ensuring consistent, effective compliance training across the organization.
• Partner with Legal, Finance, Product, and Distribution to identify compliance requirements at the outset of new initiatives, providing guidance that enables teams to move quickly within regulatory boundaries.
• Advise business stakeholders on complex and emerging compliance risk scenarios, delivering clear, practical recommendations that balance regulatory obligation with business objectives.
• Hire, manage, and develop a growing compliance team, establishing clear performance expectations and career pathways while maintaining a hands-on, player/coach presence.

Qualifications:

• 15+ years of compliance experience in financial services, including substantive experience in a senior compliance leadership role with direct management responsibility.
• Demonstrated expertise across B/D, RIA, and 40 Act compliance programs with hands-on working knowledge of the Investment Advisers Act of 1940, Investment Company Act of 1940, Securities Act of 1933, Securities Exchange Act of 1934, and applicable SEC, FINRA, NFA, and CFTC regulations.
• Proven track record of leading regulatory examinations and managing ongoing relationships with the SEC, FINRA, and/or NFA.
• Experience building, managing, and developing a compliance team of 5 or more professionals.
• Ability to deliver accurate, direct, and commercially practical compliance guidance under time pressure and in ambiguous regulatory environments.
• FINRA Series 7 and Series 24 licenses required.
• Experience with digital assets, cryptocurrency products, blockchain technology, and the evolving U.S. regulatory framework governing digital asset managers.
• Background working in a high-growth or scaling firm where compliance programs were built or significantly expanded.
• J.D. or advanced degree in a relevant discipline.
• Experience with ETFs, statutory trusts, or other registered products in novel or emerging asset classes.