Director, AI Commercialization

Block is building a new generation of AI-powered products with the potential to create entirely new ways for businesses to operate, engage with customers, and grow. We are looking for an experienced commercial leader to turn these emerging products into meaningful businesses. The Director of AI Commercialization will own the path from product to pilot to commercial validation, and turn this into a repeatable go-to-market motion across Block’s emerging AI portfolio. This role will focus on enterprise customers and strategic partners. This is a senior, highly entrepreneurial role, and requires someone who has done this before: taken technically complex, early-stage products into the market, secured sophisticated enterprise customers and partners, built and converted pilots, established pricing and commercial models, and ultimately created a sales and partnership motion that could scale. Initially, this leader will be highly hands-on. They will personally develop our most important enterprise customers and partners, structure our earliest commercial engagements, and work alongside Product and Engineering to shape what we build. As we establish product-market fit, they will determine how we scale the motion and build the organization required to support it. What You’ll Do Own AI commercialization • Develop and own the commercialization strategy for Block’s emerging AI products, including target markets, enterprise customer segments, partner types, use cases, positioning, pricing, packaging, and routes to market. • Translate technically sophisticated AI capabilities into clear, differentiated value propositions for enterprise customers and partners. • Assess market opportunities and determine where Block has the strongest right to win. • Establish clear commercial milestones and determine when products are ready to move from experimentation to broader distribution. • Operate as the senior commercial counterpart to Product and Engineering leaders building Block’s AI portfolio. • Bring together cross-functional infrastructure required to support this motion at scale. Win lighthouse enterprise customers and strategic partners • Personally source, develop, and close relationships with sophisticated enterprise customers and strategic partners. • Engage credibly with C-suite executives and senior technology, product, operations, business development, and commercial leaders. • Identify where strategic partnerships can accelerate distribution, unlock new use cases, or create differentiated product capabilities. • Sell products that may still be evolving, creating conviction around the vision while setting appropriate expectations about what exists today. • Build a portfolio of lighthouse customers and partners that provides product validation, commercial proof points, references, distribution, and a foundation for broader adoption. Build pilots that become scaled commercial relationships • Design commercial pilots with enterprise customers and partners with clear objectives, success metrics, economics, timelines, and paths to production and expansion. • Own the progression from initial conversation → pilot → production deployment or partnership launch → scaled commercial relationship. • Work directly with customers, partners, Product, and Engineering throughout early implementations. • Distinguish between strategically important market feedback and bespoke requests that should not drive the roadmap. • Use early engagements to rapidly test product-market fit, willingness to pay, partnership models, implementation requirements, and the durability of demand. Create the repeatable GTM and partnership model • Turn what we learn from early customers and partners into a scalable commercial playbook. • Establish segmentation, qualification, pricing, contracting, sales process, partner models, implementation, customer success, and expansion motions. • Determine when products should be sold directly, through strategic partners, through existing Block Sales and Partnerships teams, or through a combination of channels. • Identify opportunities to leverage Block’s existing enterprise relationships and broader ecosystem. • Build the pipeline management, forecasting, metrics, and operating cadence required to manage the business. Build the organization • Start as a hands-on commercial leader rather than immediately building a large team. • Determine what capabilities and roles are required as product-market fit develops. • Recruit and lead a high-performing commercial organization when the opportunity is ready to scale. • Create a thoughtful path for successful products to graduate from incubation into Block’s broader GTM organization where appropriate. What We’re Looking For • 15+ years of relevant commercial experience, including significant leadership responsibility in enterprise technology. • This role requires a proven commercialization leader, not simply an experienced enterprise seller or partnerships executive. • Direct, demonstrated experience taking new or emerging technology products from early market entry through commercial scale. • A track record of personally securing lighthouse enterprise customers and strategic partners, structuring pilots and partnerships, and converting them into scaled commercial relationships. • Deep experience selling complex technology to large enterprises and working with sophisticated strategic partners. • Established credibility engaging C-suite, senior technical, product, business development, and commercial executives. • Experience commercializing AI, data infrastructure, developer platforms, cloud infrastructure, or similarly complex and rapidly evolving technology. • Strong understanding of how enterprises and strategic partners evaluate, pilot, procure, integrate, distribute, and scale emerging technologies. • Demonstrated ability to develop pricing, packaging, partnership structures, commercial models, and routes to market