Director of Engineering, Thoughtful AI

• This is an ideal role for a seasoned engineering executive who thrives in complex, high-stakes environments - someone who has successfully led post-merger integrations, built strong cross-border teams, and delivered meaningful technology transformation in enterprise settings
• 10+ years of experience in software or infrastructure engineering, with 4+ years in senior engineering leadership roles
• Proven success leading post-merger or post-acquisition integrations - both technical (system unification, platform alignment) and organizational (team restructuring, culture bridging)
• Demonstrated ability to manage 10+ direct reports at Senior or Staff level over extended periods
• Strong product-oriented mindset, capable of balancing integration execution with business outcomes
• Hands-on familiarity with .NET and legacy technology stacks, with demonstrated experience modernizing or integrating them within cloud or AI platforms
• Experience leading distributed, global engineering teams, particularly across US/India collaborations
• Excellent communication skills - able to simplify complex technical topics for executive and cross-functional audiences
• Willingness and ability to travel frequently (≈50%) to Chennai, India
• Thrives in fast-moving, high-growth, post-merger environments
• Deeply motivated by the mission to improve healthcare through technology
• Understands that impact requires flexibility beyond a 9-to-5 mindset
• Builds rapport quickly across teams, functions, and cultures
• Leads with clarity, empathy, and conviction

Desirable

• We're looking for an Exceptional Director of Engineering for our Integrations team
• As the Director of Engineering, Integrations at Thoughtful AI/Smarter Technologies, you will play a pivotal role in uniting the engineering efforts of Thoughtful AI and AccessHealthcare following SmarterTechnologies’ recent acquisitions
• This role sits at the center of a transformative moment - bringing together advanced AI automation and large-scale healthcare operations to redefine what’s possible in healthcare technology
• You will serve as the primary interface between Thoughtful’s U.S. -based engineering teams and AccessHealthcare’s organization in Chennai, India, leading the integration of systems, teams, and technology into a cohesive, scalable platform
• Your mission: to build the connective framework, technical, cultural, and organizational, that enables the two entities to operate as one high-performing engineering organization
• You'll lead and scale an Integration Engineering organization (~13 Senior and Staff-level engineers) to deliver high-quality technical and organizational integration across Thoughtful AI and AccessHealthcare
• Serve as the technical and organizational bridge between U.S. and India-based teams, spending approximately 25% of your time in Chennai to ensure alignment and momentum
• Define and execute the integration roadmap, unifying systems, data flows, and automation platforms across both companies under the SmarterTechnologies umbrella
• Collaborate with Product, Engineering, and Operations leadership across Thoughtful and AccessHealthcare to design and deliver joint product offerings that combine AI-driven automation with large-scale healthcare operations
• Drive operational excellence across engineering practices, including reliability, compliance, and velocity
• Foster a culture of accountability, collaboration, and long-term retention across distributed teams
• Champion transparency and communication across time zones and functions, ensuring continuous alignment among leadership and technical stakeholders
• What Success Looks Like
• Seamless integration of Thoughtful’s automation technology into AccessHealthcare’s production environment
• Launch of joint solutions that enhance healthcare efficiency and scale
• Cross-entity collaboration that feels frictionless and purpose-driven
• Sustained team engagement and high retention through periods of change