Head of Technical Product at Grayscale Investments in Stamford, CT

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 Head of Technical Product to define and lead product across core business systems and platforms. You will operate as a player-coach, leading a team of Product Managers while staying deeply involved in defining, building, and scaling the solutions that drive the business forward. This role reports to the Chief Technology Officer and is responsible for shaping product direction and execution as we scale.  You will play a key role in shaping system architecture and solution design, working closely with Engineering to define how our platforms are built and scaled. Technology Environment: Our platform is modern and evolving, built on AWS with infrastructure managed through Terraform and containerized services across Docker and serverless environments. We utilize GitLab for CI/CD to support reliable and scalable delivery across systems.  The environment includes a mix of APIs, data pipelines, and internal systems that support both client-facing and operational workflows. AI is an emerging focus area across Grayscale, with significant opportunity to define how it is applied across internal workflows, data systems, and product capabilities. Responsibilities: Define and own product vision and strategy, translating company goals into clear roadmaps and measurable outcomes. Build, lead, and develop a high-performing team of Product Managers, establishing a strong product culture and maintaining a hands-on, player-coach approach. Set and own product priorities, aligning teams around shared goals, timelines, and measurable outcomes, and ensuring the product backlog reflects priorities. Serve as a commercial partner to the business, using customer insights and data to shape product decisions and priorities. Drive end-to-end solution architecture alignment across products, ensuring cohesive system design, scalability, and interoperability. Evaluate and make trade-off decisions across build vs. buy, technical debt, performance, and scalability to support long-term platform strategy. Lead technical discovery and solution design for complex, cross-functional initiatives, translating ambiguous business problems into well-architected systems Partner with Engineering to define system boundaries and integration patterns (APIs, event-driven architecture, data pipelines). Bring an informed perspective on industry trends and emerging technologies, shaping how they are applied across our products with a focus on responsible use of AI. Qualifications: 10+ years of experience building and owning products, platforms, or systems, ideally within fintech, SaaS, or data-driven environments. Experience leading and developing product teams, with a track record of building high-performing organizations. Demonstrated ability to define product direction in ambiguous environments and translate business objectives into scalable product and system solutions. Strong technical fluency, with the ability to engage in architecture discussions across APIs, data models, integrations, and distributed systems. Experience building or scaling products involving data platforms, workflows, or AI/ML capabilities. Track record of making tradeoff decisions across competing priorities, balancing speed, quality, and long-term platform considerations. Strong communication and influence across technical and business stakeholders. Experience operating in a scaling environment, either within a growing company or through transformation within a larger organization. Familiarity with financial services or other regulated industries is a plus. Experience working in engineering-adjacent roles or closely with technical architecture teams. Scrum Certification (Preferred). 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.