Senior Executive Assistant

Thoughtful AI is a trailblazing Series A startup on a mission to redefine the B2B landscape through pioneering AI solutions. With a culture that fosters innovation and excellence, we're making waves in the massive healthcare industry, continuously pushing the envelope of what's possible. We're seeking an elite Technical Recruiter, a tenacious individual who mirrors our pursuit of world-class standards and relentless drive.

Our ecosystem thrives on resilience, ambition, and the ceaseless pursuit of innovation. If you are passionate about making an impact and excel in high-intensity, high-reward environments, Thoughtful AI could be your next arena.

About Thoughtful AI

We are Thoughtful AI — pioneering a new approach to automation for all healthcare providers! Our Fully-Human Capable AI Agents operate within existing healthcare RCM tech stacks to accomplish key tasks currently performed by human employees. The Thoughtful platform combines state-of-the-art technology, including Robotic Process Automation, Optical Character Recognition, Natural Language Processing, and Large Language Models that function in unison to create unparalleled results for RCM departments.

About the Role:

We are looking for a highly experienced, organized, and proactive Senior Executive Assistant to support our CEO and co-founder team. This role is ideal for someone who thrives in a high-growth startup environment, enjoys working with technology and AI, and excels at managing executive operations, logistics, and strategic projects.

This role will be primarily CEO-focused (80%), ensuring seamless execution of his schedule, communications, and strategic priorities. The remaining 20% will involve supporting our other co-founder with scheduling, coordination, and communications.

Key Responsibilities:

CEO Support (80%)

• Executive Operations: Manage the CEO’s complex calendar and email communications, making strategic decisions about time allocation and prioritization.
• Meeting Coordination: Schedule and coordinate high-stakes meetings with investors, board members, and key industry partners, including preparation of briefing materials and follow-ups.
• Travel Management: Plan and execute domestic and international travel arrangements, creating detailed itineraries to maximize the CEO’s time and effectiveness.
• Strategic Projects: Drive special projects independently, from research and analysis to implementation.
• Stakeholder Management: Manage relationship dynamics with the internal leadership team and external stakeholders.
• Documentation & Communication: Prepare and review presentations, communications, and other materials for accuracy and alignment with company messaging.
• Board & Compliance Support: Coordinate board meetings and maintain critical company documentation.
• Process Optimization: Anticipate needs and create systems to streamline operations and communication flows.
• Company Events & Offsites: Plan and execute company events and offsites, ensuring seamless logistics, comms, vendor coordination, and scheduling.
• Meeting & Project Support:
• Provide proactive calendar support and make recommendations regarding prioritization, delegation, and organization.
• Contribute to team meetings and offsites by assisting with material production, taking notes, and tracking action items.
• Partner with the CEO to track key project milestones and progress against team and company goals.

Co-Founder Support (20%)

• Manage scheduling, coordination, and email communications for the second co-founder.
• Assist with logistics and planning for key meetings.
• Provide occasional support for special projects as needed.

Required Qualifications:

• 7+ years of Executive Assistant experience, with at least 3 years supporting C-level executives in a fast-paced technology environment.
• Proven experience in a high-growth startup, with a deep understanding of operational efficiency and executive support.
• Strong interest in technology and AI, with a desire to work in an innovation-driven environment.
• Exceptional written and verbal communication skills.
• Strong technical aptitude and proficiency with modern productivity tools and software.
• Experience in planning and executing company events and offsites effectively.
• Ability to anticipate needs, take initiative, and execute with high attention to detail.
• A self-starter who thrives in fast-paced, dynamic environments.

Why Join Us?

• A high-impact role where you’ll work directly with leadership.
• Opportunity to be part of a fast-growing, AI-driven company.
• Fast-paced, collaborative work environment with room for career development.
• Competitive compensation and benefits.
• A culture built on ourWarrior Manifesto.

If you're a proactive, tech-savvy executive assistant with a passion for efficiency, innovation, and event execution, we’d love to hear from you! Apply now.