Executive Assistant to the CPO

About Thoughtful AI

At Thoughtful AI, we’re 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 systems—from prior authorizations to revenue operations. Backed by leading investors and rooted in deep healthcare and technical expertise, we’re scaling fast and building a team that’s as ambitious as our mission.

The Role

We’re 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 executive’s 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 CPO’s 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 You’ll Do

• Own and manage all aspects of the CPO’s calendar—ensuring meetings are strategically scheduled and time is aligned with top priorities.
• Proactively manage and coordinate meetings, events, and internal touchpoints with CPO’s direct reports and other key stakeholders.
• Provide scheduling and logistical support (meetings, travel, briefings) to CPO’s department leads as needed—high-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 CPO’s office and internal teams.

Who You Are

• You have 5+ years of experience supporting senior executives in fast-paced, high-growth environments.
• You’re 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 professionalism—both written and verbal.
• You bring a high degree of judgment and discretion to sensitive workstreams.
• You’re 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