Chief Compliance Officer

Grayscale is the largest digital asset-focused investment platform in the world by AUM and offers the broadest selection of digital asset investment products in the U.S. based on number of products. Our platform spans the full spectrum of institutional-grade solutions—from single-asset exposures to diversified and thematic strategies—with a goal of providing every investor with access to the hyper-expanding digital asset universe.  Our firm offers a rare combination of decades of traditional finance work experience and digital asset leadership that brings an institutional mindset to the maturing digital asset industry. This convergence of capabilities positions us to deliver investment solutions and client experiences that are both institutionally robust and technologically advanced, which we believe offers a competitive edge that is difficult to replicate. We’re proud of our deep crypto expertise and work closely with individual and institutional investors as they explore this asset class as part of their portfolio allocation.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 > 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, a...