Head of Program Management

As the Head of Program Management at Thoughtful AI, you’ll lead the discipline responsible for executing our most complex, strategic, and high-value AI Agent deployments across the healthcare ecosystem. This is a critical leadership role that requires not only operational excellence but also the ability to attract, mentor, and scale a world-class team of program and project managers.

You will oversee the full lifecycle of enterprise implementations—ensuring that every deployment is executed with precision, discipline, and a relentless focus on customer outcomes. Your team will serve as the connective tissue between strategy and execution, turning bold ideas into reality by aligning internal stakeholders, external partners, and cross-functional workstreams around scalable delivery.

This is an ideal role for a leader with a proven track record of managing large-scale, enterprise technology programs and a passion for developing talent, implementing best practices, and building systems that scale.

Learn more about our Warrior culture.

• 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.

• A cohesive, high-performing program management team with strong ownership, accountability, and delivery maturity.
• Scalable, repeatable implementation frameworks that drive high-impact deployments across enterprise customers.
• Executive-level confidence in program delivery driven by transparent reporting, risk mitigation, and operational rigor.
• Seamless cross-functional collaboration with Sales, Product, Engineering, and Customer teams.
• Enterprise customers achieving transformative outcomes on time and at scale—with Thoughtful seen as a strategic partner.

• 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).

• Familiarity with revenue cycle management (RCM), healthcare operations, or payer-provider dynamics. (strongly preferred)
• 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.

• 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