“TJ Boskelly is a Revenue Operations and Sales Systems expert with deep expertise in software architecture, automation, and go-to-market strategy. With a strong background in enterprise SaaS, sales engineering, and CRM optimization, TJ specializes in designing and implementing scalable software solutions that drive efficiency and revenue growth for high-performing organizations. As the Director of Revenue Operations – Sales Systems at Datadog, TJ leads the strategy, implementation, and management of revenue technology stacks, optimizing processes across sales, marketing, finance, customer success, and product teams. His expertise in Salesforce Revenue Cloud (CPQ & Billing), sales automation, and data-driven decision-making ensures seamless execution of go-to-market initiatives. Prior to Datadog, TJ held key roles at Salesforce, where he leveraged his technical expertise to architect and implement sales and billing automation solutions, optimizing quote-to-cash processes for enterprise clients. With a passion for software development, revenue intelligence, and business process automation, TJ is a subject matter expert in software-driven revenue operations, enabling organizations to scale through technology, automation, and strategic process design. As the Director of Revenue Operations – Sales Systems at Datadog, TJ leads the strategy, implementation, and administration of revenue productivity tools, ensuring seamless integration and optimization of sales technology stacks. Prior to Datadog, he held key roles at Salesforce, where he specialized in Salesforce Revenue Cloud (CPQ and Billing), helping businesses streamline their quote-to-cash processes and optimize revenue workflows. With expertise in CRM architecture, sales process automation, and revenue analytics, TJ enables organizations to maximize sales efficiency and drive sustainable revenue growth. Passionate about leveraging technology to enhance go-to-market execution, he plays a pivotal role in aligning sales strategy with scalable, data-driven solutions.”