Lead Technical Program Manager

About the Role

As a Lead Technical Program Manager at Thoughtful AI, you’ll play a key role in shaping the delivery of our most complex and high-value AI Agent deployments across the healthcare ecosystem. This is a hands-on leadership role where you’ll manage a team of 5–7 Technical Program Managers, guide their work, and ensure their outputs meet the highest standards of quality and impact.

Reporting to the Director of Technical Program Management, you will balance three core responsibilities:

1. People management – building and developing a high-performing team of TPMs.
2. Project mentorship – reviewing TPM deliverables, providing feedback, and coaching team members before their work is implemented.
3. Strategic initiatives – contributing to cross-functional efforts that improve how Thoughtful delivers at scale.

On customer projects, you’ll partner closely with TPMs during the discovery phase—leading process overviews that set the stage for successful implementations. Your TPMs will then own the design, build, and deployment of AI Agents, with your ongoing guidance and mentorship ensuring excellence throughout.

This is an ideal role for a proven program management leader who thrives on developing talent, improving delivery practices, and helping enterprise customers achieve transformative outcomes.

Learn more about our Warrior culture.

Your Mission

• Manage and mentor a team of 5–7 Technical Program Managers, fostering growth, accountability, and delivery excellence.
• Own customer-facing deliveries directly, serving as the assigned TPM on select accounts while modeling delivery best practices.
• Review TPM deliverables (product requirements documents, delivery roadmaps, etc.) and provide actionable feedback to raise quality before customer-facing execution.
• Partner with TPMs during discovery phases to lead process overviews and ensure accurate foundations for solution design.
• Contribute to strategic initiatives that improve delivery frameworks, governance, and cross-functional collaboration.
• Act as a trusted partner to Sales, Customer Success, Product, and Engineering to ensure delivery capabilities align with customer expectations.
• Champion best practices, risk management approaches, and scalable frameworks that enable consistent, enterprise-grade deployments.
• Represent program delivery in leadership conversations and customer forums, bringing forward insights and solutions.

What Success Looks Like

• A cohesive TPM team with strong ownership, confidence, and consistent delivery quality.
• Scalable, repeatable practices adopted across projects, driving enterprise-grade deployments.
• TPMs consistently producing high-quality outputs that accelerate delivery and reduce risk.
• Cross-functional leaders relying on TPMs (and you as their lead) as trusted partners in execution.
• Enterprise customers achieving transformative outcomes with confidence in Thoughtful’s delivery approach.

What You Bring

• 8-12+ years of experience in program or technical project management, including leadership responsibility for developing and managing teams.
• Proven success in enterprise technology implementations, ideally within SaaS, consulting, automation, or healthcare technology.
• Strong background in healthcare delivery; experience in Revenue Cycle Management is a plus
• Experience mentoring or reviewing project/program management outputs to ensure quality before execution.
• Strategic perspective combined with executional discipline - you can coach the details while influencing the bigger picture.
• Ability to influence senior stakeholders and customers through clear, data-driven communication.
• Comfort navigating fast-paced, ambiguous environments and building structure where it doesn’t yet exist.
• Bachelor’s degree in a technical, operational, or business discipline (MBA or equivalent experience a plus).

Thoughtful AI Benefits

• 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