<h3><strong>Opportunity</strong></h3> <p>As the <strong>Head of Program Management</strong> 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.</p> <p>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.</p> <p>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.</p> <p>Learn more about our <a href="https://www.thoughtful.ai/blog/being-a-warrior-at-thoughtful-ai-a-manifesto-for-excellence" target="_blank"><strong><em>Warrior culture</em></strong></a>.</p> <h3><strong>Key Responsibilities</strong></h3> <ul> <li>Build, lead, and mentor a high-performing team of program managers responsible for executing AI Agent implementations across large healthcare systems.</li> <li>Define and own the program management vision, strategy, tools, and frameworks that drive consistent, repeatable, enterprise-grade delivery.</li> <li>Guide your team in orchestrating complex deployments across multiple customers, products, and internal departments—ensuring accountability, transparency, and momentum.</li> <li>Act as a strategic partner to Sales, Customer Success, Product, and Engineering leaders to ensure customer expectations are aligned with delivery capabilities.</li> <li>Implement and evolve best practices, delivery frameworks, risk management approaches, and governance structures that allow Thoughtful to scale deployments confidently and predictably.</li> <li>Represent program delivery in executive conversations, customer briefings, and internal planning forums—bringing data, insight, and foresight to every table.</li> <li>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.</li> </ul> <h3><strong>What Success Looks Like</strong></h3> <ul> <li>A cohesive, high-performing program management team with strong ownership, accountability, and delivery maturity.</li> <li>Scalable, repeatable implementation frameworks that drive high-impact deployments across enterprise customers.</li> <li>Executive-level confidence in program delivery driven by transparent reporting, risk mitigation, and operational rigor.</li> <li>Seamless cross-functional collaboration with Sales, Product, Engineering, and Customer teams.</li> <li>Enterprise customers achieving transformative outcomes on time and at scale—with Thoughtful seen as a strategic partner.</li> </ul> <h3><strong>Minimum Qualifications</strong></h3> <ul> <li>8–12+ years of experience in program delivery leadership, with direct responsibility for scaling complex, multi-million dollar enterprise technology implementations.</li> <li>Experience leading and developing program or project management teams in high-growth SaaS, consulting, automation, or healthcare technology environments.</li> <li>Strong command of delivery methodologies (Agile, waterfall, hybrid) and the judgment to know when and how to apply them.</li> <li>A strategic mindset combined with deep executional discipline—you see the big picture and drive the details.</li> <li>Proven ability to influence senior internal and customer stakeholders with data, clarity, and confidence.</li> <li>Comfort in fast-paced, ambiguous environments where structure is built, not inherited.</li> <li>Exceptional written and verbal communication skills with an ability to simplify complexity and drive alignment.</li> <li>Bachelors degree in a technical, operational, or business discipline (MBA or equivalent experience a plus).</li> </ul> <h3><strong>Bonus Points</strong></h3> <ul> <li>Familiarity with revenue cycle management (RCM), healthcare operations, or payer-provider dynamics. (strongly preferred)</li> <li>Experience working with AI platforms, automation technologies, agent-based systems or RPA.</li> <li>Advanced proficiency with tools such as Jira, Notion, Looker, or other enterprise PM and BI software.</li> </ul> <h3> </h3> <h3>Thoughtful AI Benefits</h3> <ul> <li>Market-leading base salary and bonus</li> <li>Employee stock options</li> <li>Medical, dental, and vision insurance for you and your dependents</li> <li>We expect you to unwind and disconnect for three weeks per year while still getting paid</li> </ul><div><div><div>California Salary Range </div><div><span>$200,000</span><span>—</span><span>$250,000 USD</span></div></div></div>

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