Thoughtful AI
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Executive Assistant to the CPO
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Thoughtful AI . About Thoughtful AI
At Thoughtful AI, were building Smarter Technologies that deliver better care. Our mission is to transform the way healthcare operates by embedding intelligent, adaptive automation into the workflows that power our systemsfrom prior authorizations to revenue operations. Backed by leading investors and rooted in deep healthcare and technical expertise, were scaling fast and building a team thats as ambitious as our mission. The Role
Were looking for a detail-oriented and highly organized Executive Assistant to support our Chief Product Officer (CPO). This is a critical support role for an EA who thrives in dynamic environments and can seamlessly manage the complexity of a senior executives calendar, email, meetings, task management, team logistics, and travel. In addition to supporting the CPO directly, this role will also provide light calendaring and logistics support to the CPOs direct reports as needed. This is a role for someone who is highly responsive, has a strong sense of judgment, and takes pride in enabling leaders to operate at peak efficiency. This role will also require taking on special projects to support the CPO and his team. What Youll Do
Own and manage all aspects of the CPOs calendarensuring meetings are strategically scheduled and time is aligned with top priorities. Proactively manage and coordinate meetings, events, and internal touchpoints with CPOs direct reports and other key stakeholders. Provide scheduling and logistical support (meetings, travel, briefings) to CPOs department leads as neededhigh-leverage assistance that helps the whole org run more smoothly. Coordinate complex travel planning and itineraries across time zones. Prepare and organize materials for key meetings (e.g., agendas, briefing docs, notes). Monitor the CPO's inbox, identifying areas that need action and supporting the CPO by proactively using discretion to handle action items, clearly communicating what's been completed and what still needs attention, then blocking his time to ensure nothing gets missed. Maintain discretion and handle confidential information with care and professionalism. Serve as a dependable liaison between the CPOs office and internal teams. Who You Are
You have 5+ years of experience supporting senior executives in fast-paced, high-growth environments. Youre a highly organized and responsive calendar and logistics pro. You take ownership of your work, anticipate needs, and solve problems before they arise. You communicate with clarity, calmness, and professionalismboth written and verbal. You bring a high degree of judgment and discretion to sensitive workstreams. Youre energized by helping leaders stay focused and effective. You work well independently, but collaborate with empathy and curiosity. Experience supporting multiple stakeholders simultaneously is a plus. Experience in healthcare or tech/startups is a plus. Why Thoughtful AI
Mission-driven work transforming healthcare High-trust, high-autonomy environment Competitive compensation & equity Flexible remote work (Austin-based hybrid preferred) Comprehensive health, dental & vision benefits 401(k) and parental leave Smart, collaborative, and values-aligned team Compensation and Details
California Salary Range: $140,000$190,000 USD Seniority level
Mid-Senior level Employment type
Full-time Job function
Administrative Industries
Software Development
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Executive Assistant to the CPO
role at
Thoughtful AI . About Thoughtful AI
At Thoughtful AI, were building Smarter Technologies that deliver better care. Our mission is to transform the way healthcare operates by embedding intelligent, adaptive automation into the workflows that power our systemsfrom prior authorizations to revenue operations. Backed by leading investors and rooted in deep healthcare and technical expertise, were scaling fast and building a team thats as ambitious as our mission. The Role
Were looking for a detail-oriented and highly organized Executive Assistant to support our Chief Product Officer (CPO). This is a critical support role for an EA who thrives in dynamic environments and can seamlessly manage the complexity of a senior executives calendar, email, meetings, task management, team logistics, and travel. In addition to supporting the CPO directly, this role will also provide light calendaring and logistics support to the CPOs direct reports as needed. This is a role for someone who is highly responsive, has a strong sense of judgment, and takes pride in enabling leaders to operate at peak efficiency. This role will also require taking on special projects to support the CPO and his team. What Youll Do
Own and manage all aspects of the CPOs calendarensuring meetings are strategically scheduled and time is aligned with top priorities. Proactively manage and coordinate meetings, events, and internal touchpoints with CPOs direct reports and other key stakeholders. Provide scheduling and logistical support (meetings, travel, briefings) to CPOs department leads as neededhigh-leverage assistance that helps the whole org run more smoothly. Coordinate complex travel planning and itineraries across time zones. Prepare and organize materials for key meetings (e.g., agendas, briefing docs, notes). Monitor the CPO's inbox, identifying areas that need action and supporting the CPO by proactively using discretion to handle action items, clearly communicating what's been completed and what still needs attention, then blocking his time to ensure nothing gets missed. Maintain discretion and handle confidential information with care and professionalism. Serve as a dependable liaison between the CPOs office and internal teams. Who You Are
You have 5+ years of experience supporting senior executives in fast-paced, high-growth environments. Youre a highly organized and responsive calendar and logistics pro. You take ownership of your work, anticipate needs, and solve problems before they arise. You communicate with clarity, calmness, and professionalismboth written and verbal. You bring a high degree of judgment and discretion to sensitive workstreams. Youre energized by helping leaders stay focused and effective. You work well independently, but collaborate with empathy and curiosity. Experience supporting multiple stakeholders simultaneously is a plus. Experience in healthcare or tech/startups is a plus. Why Thoughtful AI
Mission-driven work transforming healthcare High-trust, high-autonomy environment Competitive compensation & equity Flexible remote work (Austin-based hybrid preferred) Comprehensive health, dental & vision benefits 401(k) and parental leave Smart, collaborative, and values-aligned team Compensation and Details
California Salary Range: $140,000$190,000 USD Seniority level
Mid-Senior level Employment type
Full-time Job function
Administrative Industries
Software Development
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