<p><strong>Join Our Mission to Revolutionize Healthcare</strong></p> <p><a href="http://thoughtful.ai/">Thoughtful</a> 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.</p> <p><strong>Were looking for an Exceptional Director of Engineering for our Integrations team.</strong></p> <h2><span>Opportunity</span></h2> <p>As the <strong>Director of Engineering, Integrations</strong> 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.</p> <p>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.</p> <p>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.</p> <p><em>Learn more about our </em><a href="https://www.thoughtful.ai/blog/being-a-warrior-at-thoughtful-ai-a-manifesto-for-excellence"><em>Warrior culture</em></a><em>.</em></p> <h2><span>Key Responsibilities</span></h2> <ul> <li>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.</li> <li>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.</li> <li>Define and execute the integration roadmap, unifying systems, data flows, and automation platforms across both companies under the SmarterTechnologies umbrella.</li> <li>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.</li> <li>Drive operational excellence across engineering practices, including reliability, compliance, and velocity.</li> <li>Foster a culture of accountability, collaboration, and long-term retention across distributed teams.</li> <li>Champion transparency and communication across time zones and functions, ensuring continuous alignment among leadership and technical stakeholders.</li> </ul> <h2><span>What Success Looks Like</span></h2> <ul> <li>Seamless integration of Thoughtful’s automation technology into AccessHealthcare’s production environment.</li> <li>Launch of joint solutions that enhance healthcare efficiency and scale.</li> <li>Cross-entity collaboration that feels frictionless and purpose-driven.</li> <li>Sustained team engagement and high retention through periods of change.</li> </ul> <h2><span>Minimum Qualifications</span></h2> <ul> <li>10+ years of experience in software or infrastructure engineering, with 4+ years in senior engineering leadership roles.</li> <li>Proven success leading post-merger or post-acquisition integrations - both technical (system unification, platform alignment) and organizational (team restructuring, culture bridging).</li> <li>Demonstrated ability to manage 10+ direct reports at Senior or Staff level over extended periods.</li> <li>Strong product-oriented mindset, capable of balancing integration execution with business outcomes.</li> <li>Hands-on familiarity with .NET and legacy technology stacks, with demonstrated experience modernizing or integrating them within cloud or AI platforms.</li> <li>Experience leading distributed, global engineering teams, particularly across US/India collaborations.</li> <li>Excellent communication skills - able to simplify complex technical topics for executive and cross-functional audiences.</li> <li>Willingness and ability to travel frequently (≈50%) to Chennai, India.</li> </ul> <h2><span>Preferred Qualifications</span></h2> <ul> <li>Experience integrating or operating in healthcare technology or Revenue Cycle Management (RCM) domains.</li> <li>Background in regulated or compliance-heavy environments (e.g., SOC 2, HIPAA).</li> <li>Demonstrated success building long-term, high-performing teams through major organizational transitions.</li> <li>Proven ability to design and launch joint product offerings across multiple business entities.</li> </ul> <h2><span>Cultural Attributes</span></h2> <ul> <li>Thrives in fast-moving, high-growth, post-merger environments.</li> <li>Deeply motivated by the mission to improve healthcare through technology.</li> <li>Understands that impact requires flexibility beyond a 9-to-5 mindset.</li> <li>Builds rapport quickly across teams, functions, and cultures.</li> <li>Leads with clarity, empathy, and conviction.</li> </ul> <p><span><strong>Why Thoughtful?</strong></span></p> <ul> <li>Competitive compensation</li> <li>Equity participation: Employee Stock Options.</li> <li>Health benefits: Comprehensive medical, dental, and vision insurance.</li> <li>Time off: Generous leave policies and paid company holidays.</li> </ul> <p> </p><div><div><div>California Salary Range </div><div><span>$240,000</span><span>—</span><span>$300,000 USD</span></div></div></div>

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