Executive Assistant

Summary

Join Thoughtful AI as an Executive Assistant to the Chief Product Officer (CPO), providing comprehensive support in a dynamic healthcare technology environment. You will manage the CPO's complex calendar, coordinate meetings and travel, prepare materials, and handle confidential information. This role requires proactive problem-solving, excellent communication, and the ability to anticipate needs. You will also provide logistical support to the CPO's direct reports. The ideal candidate has 5+ years of experience supporting senior executives in fast-paced settings and thrives in a collaborative, high-trust environment. Thoughtful AI offers competitive compensation, equity, flexible remote work options, and comprehensive benefits.

Requirements

• 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

Responsibilities

• 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

Preferred Qualifications

• Experience supporting multiple stakeholders simultaneously is a plus
• Experience in healthcare or tech/startups is a plus

Benefits

• Competitive compensation & equity
• Flexible remote work (Austin-based hybrid preferred)
• Comprehensive health, dental & vision benefits
• 401(k) and parental leave