Thoughtful AI

Lead and scale a program management team to execute complex AI deployments in healthcare, ensuring operational excellence and stakeholder alignment. | 8-12+ years in program delivery leadership for enterprise technology, experience with SaaS or healthcare tech, strong delivery methodology knowledge, and excellent communication and strategic skills. | Opportunity 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. Key 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. What Success Looks Like • 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. Minimum Qualifications • 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). Bonus Points • 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. Thoughtful AI 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 California Salary Range $200,000—$250,000 USD