Director of System Integrations, Smarter Technologies

• This position is ideal for a leader who thrives in high-velocity, execution-first environments and has a strong foundation in management consulting, enterprise systems delivery, or M&A integrations
• 10+ years of experience in technical program management, system integration, or implementation leadership
• Proven success delivering large-scale enterprise technology programs (preferably in SaaS, automation, or healthcare ecosystems)
• Background in management consulting (Deloitte, Accenture, PwC, BCG) or corporate integration/M&A delivery
• Strong operational acumen — excels in process, structure, and global coordination
• Experience managing distributed teams across multiple time zones and delivery centers
• Exceptional communication and executive presence; comfortable influencing across technical and business audiences
• Willingness to travel internationally up to 50% of the year, including frequent extended stays in Chennai, India
• Bachelor’s degree in business, engineering, or a related technical field (MBA a plus)
• Exposure to healthcare technology or revenue cycle management (RCM) systems

Desirable

• As the Director of System Integrations at Thoughtful AI, you’ll lead the execution of our most operationally complex and globally distributed implementation programs
• You’ll be directly responsible for delivering on customer contracts that blend human operations (in Chennai, India) with cutting-edge automation technology developed in the U.S
• This hands-on, delivery-focused leadership role requires deep expertise in technical implementation, cross-system integrations, and global program management
• You will own the Smarter Access program line, with scalable, repeatable processes that enable Thoughtful AI to execute with speed, visibility, and precision across continents
• You’ll help operationalize how humans and AI collaborate globally to transform healthcare revenue cycle management
• Lead Global System Integrations: Drive end-to-end delivery of Smarter Access programs—integrating human workflows technology deployments to ensure seamless, high-quality execution
• Build and Manage a Global Delivery Organization: Establish and lead a distributed team of program managers and ICs across the U.S. and India. Foster a culture of ownership, visibility, and delivery excellence
• Operational Process Automation: Identify delivery bottlenecks and build automation frameworks, dashboards, and reporting tools that drive consistency and efficiency across global operations
• Cross-Functional Partnership: Collaborate with Product, Engineering, Customer Success, and Operations teams to ensure system integrations align with product roadmaps and customer needs
• Governance & Reporting: Develop transparent reporting frameworks that track global program health, delivery velocity, and risk across human and AI workstreams
• Customer-Facing Delivery Leadership: Represent system integration delivery in executive and client-facing discussions, ensuring stakeholder alignment and confidence
• What Success Looks Like
• Global integration delivery structure is operational within the first two quarters
• Scalable, transparent frameworks connecting India-based execution with U.S. product and engineering teams
• Increased automation and visibility into how systems, people, and processes interact across the global delivery model
• Chennai operations are running with clarity, accountability, and predictable outcomes
• Strong partnership with the Head of Program Management, ensuring seamless collaboration across Thoughtful’s Smarter Access and Smarter Agents programs