Executive Assistant to the CPO
@ Thoughtful AI

Hybrid
$165,000
Hybrid
Full Time
Posted 23 days ago

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XXXXXXXXX XXXXXXXXXXX XXXXXXXXX****** @thoughtful.ai
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Job Details

About Thoughtful AI

At Thoughtful AI, we’re building Smarter Technologies that deliver better care. Our mission is to transform healthcare by embedding intelligent, adaptive automation into workflows that power systems—from prior authorizations to revenue operations. Backed by leading investors with deep healthcare and tech expertise, we’re scaling fast.

The Role

We are looking for a detail-oriented and highly organized Executive Assistant to the CPO. You will manage the CPO's calendar, email, meetings, task management, team logistics, and travel, while also supporting his direct reports when needed. This role involves managing special projects and handling confidential information with discretion.

What You’ll Do

  • Own and manage all aspects of the CPO’s calendar.
  • Coordinate meetings, events, and internal touchpoints.
  • Provide scheduling, travel, and logistical support.
  • Prepare materials for key meetings and manage communications.
  • Serve as a crucial liaison between the CPO’s office and internal teams.

Who You Are

  • 5+ years experience supporting senior executives in fast-paced environments.
  • Highly organized with excellent calendar and logistics management skills.
  • Proactive, with strong judgment and discretion.
  • Effective communicator with clarity and professionalism.
  • 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 with Austin-based hybrid preference.
  • Comprehensive benefits including health, dental, vision, 401(k), and parental leave.

California Salary Range

$140,000—$190,000 USD

Key skills/competency

  • Calendar Management
  • Travel Coordination
  • Logistics
  • Scheduling
  • Communication
  • Discretion
  • Confidentiality
  • Organization
  • Project Support
  • Healthcare/Tech
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How to Get Hired at Thoughtful AI

🎯 Tips for Getting Hired

  • Research Thoughtful AI: Understand their mission and recent initiatives.
  • Tailor your resume: Highlight executive support and logistics skills.
  • Showcase experience: Emphasize success in fast-paced roles.
  • Prepare for interviews: Focus on problem-solving and discretion.

📝 Interview Preparation Advice

Technical Preparation

Review calendar management tools thoroughly.
Familiarize with travel booking software.
Practice coordination of multi-timezone meetings.
Brush up on office productivity tools.

Behavioral Questions

Explain handling confidential information effectively.
Describe prioritizing multiple tasks simultaneously.
Share decision-making in fast-paced scenarios.
Discuss managing demanding executive schedules.

Frequently Asked Questions