Join Our Mission to Revolutionize Healthcare

Thoughtful is pioneering a new approach to automation for all healthcare providers! Our AI-powered Revenue Cycle Automation platform enables the healthcare industry to automate and improve its core business operations.

We're looking for an Exceptional Director of Engineering for our Integrations team.

Opportunity

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.

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.

Learn more about our Warrior culture.

Key Responsibilities

• 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.

Minimum Qualifications

• 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.

Preferred Qualifications

• Experience integrating or operating in healthcare technology or Revenue Cycle Management (RCM) domains.
• Background in regulated or compliance-heavy environments (e.g., SOC 2, HIPAA).
• Demonstrated success building long-term, high-performing teams through major organizational transitions.
• Proven ability to design and launch joint product offerings across multiple business entities.

Cultural Attributes

• 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.

Why Thoughtful?

• Competitive compensation
• Equity participation: Employee Stock Options.
• Health benefits: Comprehensive medical, dental, and vision insurance.
• Time off: Generous leave policies and paid company holidays.