Grayscaleinvestments is hiring a

Web3 Head of Technology

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 is seeking a Head of Technology to lead all aspects of technology across the firm, including both Engineering and Product. This leader will own today’s holistic technology stack while shaping the design for the future, driving alignment between business objectives and scalable technology solutions. Reporting into the Chief Operating Officer, this role serves as a key strategic and commercial partner, ensuring that technology is integrated into the firm’s growth, operations, and client experience. The Head of Technology will partner closely with the CISO, while managing the engineering and product teams, to ensure resiliency, forward-looking vision, and secure, efficient technology delivery. This is a player-coach role: the ideal candidate can speak deeply with engineers on technical details and step up as a cross-functional leader shaping the long-term roadmap. The Head of Technology will ensure technology is an enabler of business growth, regulatory compliance, and innovation. Responsibilities: Leadership and Strategy

Lead all aspects of technology at Grayscale; managing Product and Engineering as a unified function, fostering collaboration and accountability. Act as a strategic and commercial partner to the COO and executive team, ensuring technology aligns with and drives firmwide priorities. Define and execute a long-term technology [and data] vision to balance innovation, scalability, security, and cost efficiency, while guiding prioritization across technology and providing visibility to the COO and executive team. Translate business priorities in areas such as client onboarding, investor reporting, fund operations, and regulatory compliance into a clear technology roadmap. Identify and evaluate opportunities to apply AI and automation across operations, data, and client platforms, ensuring innovation is balanced with compliance and risk management. Encourage adoption of modern engineering practices and pragmatic product design. Evaluate when to build versus buy, applying a flexible, cost-conscious approach to solutions.

Infrastructure and Organizational Management

Oversee current technology platforms, databases, and applications, ensuring reliable, scalable, and secure delivery across the business. Manage the technology budget, resource allocation, and vendor relationships to ensure efficient and scalable delivery aligned with firm priorities. Drive vendor management and key strategic partnerships that expand and strengthen Grayscale’s technology capabilities.

Organizational Resiliency

Build resiliency and bench strength across the technology function, ensuring continuity and succession depth through both internal talent and vendor relationships. Partner with the CISO to embed security principles into all aspects of technology design and delivery, with particular emphasis on cloud security, data protection, and regulatory compliance. Mentor leaders across technology, fostering a culture of ownership, innovation, and collaboration. Partner with cross-functional leaders in finance, operations, compliance, and client-facing teams to ensure technology is a proactive enabler of growth while also monitoring emerging regulatory requirements to maintain compliance.

 Qualifications:

12–15+ years of progressive experience in technology leadership, in both product and engineering. Track record of scaling technology in both startup or early-stage settings and in highly regulated industries such as financial services or healthcare. Strong background in managing cloud-first platforms, data strategy, governance, and architecture, and enterprise applications. Ability to engage directly with engineers on technical details while operating effectively with executive and commercial stakeholders. Experience partnering with security and integrating security into tech design and delivery with exposure to cloud and data security best practices. Demonstrated success in building and leading high-performing product and engineering teams. Excellent strategic, analytical, and communication skills, with the ability to influence both technical and business audiences. Strong preference for experience managing both product and engineering functions. Awareness of AI/automation trends and ability to evaluate their application in regulated, client-facing environments. We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

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