Executive Assistant to the CEO

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 high-caliber, trusted Executive Assistant to support our CEO. This is a critical, dynamic role for a proactive, organized, and resourceful professional who thrives in fast-paced environments and takes ownership end-to-end. You’ll be the right hand to two of our most senior leaders—responsible for optimizing their schedules, keeping them focused on their most important priorities, and helping Thoughtful run smoothly at the highest levels.

This is not your average EA role. It’s for someone who sees three steps ahead, thrives on solving for ambiguity, and brings precision, poise, and discretion to every interaction.

What You’ll Do

• Own all aspects of calendaring and scheduling for the CEO - anticipating conflicts, managing shifting priorities, and ensuring they are always where they need to be. Being context aware is key!
• Serve as a gatekeeper and force multiplier—protecting executive time and helping prioritize what matters most.
• Coordinate internal and external meetings, including board meetings, investor calls, and key cross-functional syncs.
• Provide light personal support for the CEO (e.g., travel logistics, occasional errands, gifting, etc.)
• Partner with our Office Manager in Austin on occasional in-office coordination (though this is not an office management role).
• Ensure smooth travel planning and itinerary management across multiple time zones.
• Prepare briefing materials, notes, and follow-ups for key meetings.
• Handle confidential information with discretion and judgment.
• Support hiring and managing personal assistant who will support CEO with personal and family related work

Who You Are

• You have 5+ years of experience supporting C-level executives in high-growth or fast-paced environments.
• You are an exceptional communicator - clear, concise, and thoughtful in every format.
• You are a radical owner of all your work taking pride and accountability to ensure all work is top tier.
• You’re a scheduling and logistics wizard. Nothing falls through the cracks on your watch.
• You operate with a high degree of professionalism, discretion, and integrity.
• You are obsessively organized and systems-oriented, always thinking about how to improve processes and anticipate needs.
• You are a proactive problem solver. You don’t wait to be told what to do—you see what needs to be done and go do it.
• You’re energized by being behind the scenes, enabling others to be their best and most effective.
• Willingness to travel occasionally to support CEO during high profile trips.
• You’re comfortable working remotely, but thrive in high-collaboration environments.
• Experience in healthcare or tech/startups a plus.
• Experience managing a personal assistant a plus.

Why Thoughtful AI

• Meaningful work that transforms the future of healthcare
• Mission-driven, values-oriented team
• Competitive compensation & equity
• Generous health, dental & vision benefits
• 401(k) and parental leave
• Smart, kind colleagues who are serious about their work but don’t take themselves too seriously

Originally posted on Himalayas