Head of Program Management

Summary

Join Thoughtful AI as the Head of Program Management and lead the execution of complex, strategic AI Agent deployments in healthcare. Oversee the entire lifecycle of enterprise implementations, ensuring precision and customer focus. Build and mentor a high-performing program management team, defining the vision, strategy, and frameworks for consistent delivery. Collaborate with various departments (Sales, Customer Success, Product, Engineering) to align customer expectations with delivery capabilities. Implement best practices and governance structures for scalable deployments. Represent program delivery in executive conversations and customer briefings. This role requires strong leadership, operational excellence, and a proven track record in managing large-scale technology programs.

Requirements

• 8–12+ years of experience in program delivery leadership, with direct responsibility for scaling complex, multi-million dollar enterprise technology implementations
• Experience leading and developing program or project management teams in high-growth SaaS, consulting, automation, or healthcare technology environments
• Strong command of delivery methodologies (Agile, waterfall, hybrid) and the judgment to know when and how to apply them
• A strategic mindset combined with deep executional discipline—you see the big picture and drive the details
• Proven ability to influence senior internal and customer stakeholders with data, clarity, and confidence
• Comfort in fast-paced, ambiguous environments where structure is built, not inherited
• Exceptional written and verbal communication skills with an ability to simplify complexity and drive alignment
• Bachelor's degree in a technical, operational, or business discipline (MBA or equivalent experience a plus)

Responsibilities

• Build, lead, and mentor a high-performing team of program managers responsible for executing AI Agent implementations across large healthcare systems
• Define and own the program management vision, strategy, tools, and frameworks that drive consistent, repeatable, enterprise-grade delivery
• Guide your team in orchestrating complex deployments across multiple customers, products, and internal departments—ensuring accountability, transparency, and momentum
• Act as a strategic partner to Sales, Customer Success, Product, and Engineering leaders to ensure customer expectations are aligned with delivery capabilities
• Implement and evolve best practices, delivery frameworks, risk management approaches, and governance structures that allow Thoughtful to scale deployments confidently and predictably
• Represent program delivery in executive conversations, customer briefings, and internal planning forums—bringing data, insight, and foresight to every table
• Own the quality, timeliness, and operational excellence of our largest implementations, empowering your team to drive results while removing roadblocks and setting the standard for excellence

Preferred Qualifications

• Familiarity with revenue cycle management (RCM), healthcare operations, or payer-provider dynamics
• Experience working with AI platforms, automation technologies, agent-based systems or RPA
• Advanced proficiency with tools such as Jira, Notion, Looker, or other enterprise PM and BI software

Benefits

• Market-leading base salary and bonus
• Employee stock options
• 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