Thoughtful AI · 3 days ago
Director of System Integrations
Austin, Texas Metropolitan Area
Full-time
Hybrid
Director/Executive
$200K/yr - $250K/yr
10+ years expThoughtful AI is seeking a Director of System Integrations to lead complex implementation programs that blend human operations with automation technology. This role requires deep expertise in technical implementation and global program management, focusing on operational excellence and collaboration across teams.
Artificial Intelligence (AI)Enterprise SoftwareHealth CareRobotic Process Automation (RPA)
Responsibilities
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
Qualification
Required
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
Preferred
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
Benefits
Market-leading base salary and bonus
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
Company
Thoughtful AI
Thoughtful AI provides an AI operating system designed specifically for healthcare revenue cycle management teams.
51-200 employees
H1B Sponsorship
Thoughtful AI has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2023 (1)
Funding
Current Stage
Growth StageTotal Funding
$35.83MKey Investors
New Mountain CapitalDrive Capital
2025-04-10Private Equity
2024-04-19Series A· $20M
2022-03-31Seed· $10M
Leadership Team
Alex Zekoff
Co-Founder, CEO
Chris Williams
SVP of Customer Engineering, Security, and Support
Recent News
2025-10-03
Company data provided by crunchbase