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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 operational excellence and 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 each deployment is executed with precision, discipline, and a focus on customer outcomes. Your team will connect strategy and execution, turning ideas into reality by aligning stakeholders, partners, and workstreams around scalable delivery.
This role suits a leader with a proven track record of managing large-scale enterprise technology programs, developing talent, implementing best practices, and building scalable systems.
Key Responsibilities
- Build, lead, and mentor a high-performing team of program managers responsible for AI Agent implementations in large healthcare systems.
- Define and own the program management vision, strategy, tools, and frameworks for enterprise-grade delivery.
- Guide your team in orchestrating complex deployments across multiple customers, products, and departments—ensuring accountability, transparency, and momentum.
- Act as a strategic partner to Sales, Customer Success, Product, and Engineering leaders to align delivery with customer expectations.
- Implement and evolve best practices, delivery frameworks, risk management, and governance to scale deployments confidently.
- Represent program delivery in executive discussions, customer briefings, and planning forums—bringing data, insights, and foresight.
- Own the quality, timeliness, and operational excellence of large implementations, removing roadblocks and setting standards of excellence.
What Success Looks Like
- A cohesive, high-performing program management team with ownership, accountability, and maturity.
- Scalable, repeatable implementation frameworks for impactful enterprise deployments.
- Confidence in program delivery from executives through transparent reporting, risk mitigation, and operational rigor.
- Seamless collaboration with Sales, Product, Engineering, and Customer teams.
- Enterprise customers achieving transformative outcomes on time and at scale, with Thoughtful as a strategic partner.
Minimum Qualifications
- 8–12+ years of experience leading and scaling complex, multi-million dollar enterprise technology implementations.
- Experience managing program or project teams in SaaS, consulting, automation, or healthcare tech environments.
- Strong command of Agile, Waterfall, or hybrid methodologies and judgment on applying them.
- A strategic mindset with deep executional discipline—seeing the big picture and managing details.
- Ability to influence senior stakeholders with data, clarity, and confidence.
- Comfort in fast-paced, ambiguous environments where structure is built, not inherited.
- Exceptional communication skills, simplifying complexity and driving alignment.
- Bachelor’s degree in a technical, operational, or business discipline; MBA or equivalent preferred.
Bonus Points
- Familiarity with revenue cycle management, healthcare operations, or payer-provider dynamics (preferred).
- Experience with AI platforms, automation, agent-based systems, or RPA.
- Proficiency with tools like Jira, Notion, Looker, or other enterprise PM and BI software.
Thoughtful AI Benefits
- Market-leading salary and bonus
- Employee stock options
- Medical, dental, and vision insurance for you and dependents
- Three weeks paid time off for unwinding and disconnecting
California Salary Range
$200,000—$250,000 USD
Seniority level
- Executive
Employment type
- Full-time
Job function
- Project Management and Information Technology
Industries
- Software Development