Director of System Integrations

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.

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. 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.
  
• Travel & Onsite Leadership:
  
• Travel to Chennai, India, approximately 50% of the year for at least the first 12 months to build delivery infrastructure, leadership relationships, and operational trust.
• Candidates interested in temporary relocation to Chennai for one year are strongly encouraged to apply.

• 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.

• 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.

• Experience with AI-driven automation, RPA, or agentic workflows in enterprise environments.
• Demonstrated success in building delivery frameworks or playbooks from scratch.
• History of leading integration programs post-acquisition or during major operational transitions.
  

• Market-leading base salary and bonus
• Employee stock
• Medical, dental, and vision insurance for you and your dependents
• We expect you to unwind and disconnect for three weeks per year while still getting paid