Senior Executive Assistant

Summary

Join Thoughtful AI, a Series A startup revolutionizing B2B healthcare with AI solutions, as a Senior Executive Assistant. This role provides high-impact support to the CEO (80%) and co-founder (20%), encompassing executive operations, meeting coordination, travel management, strategic projects, and stakeholder management. You will manage complex calendars, communications, and strategic priorities, plan company events, and contribute to process optimization. The ideal candidate possesses 7+ years of executive assistant experience, including 3+ years supporting C-level executives in a fast-paced technology environment, and thrives in high-growth startups. Thoughtful AI offers a competitive compensation and benefits package, a collaborative work environment, and opportunities for career development.

Requirements

• 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

Responsibilities

• Manage the CEO’s complex calendar and email communications, making strategic decisions about time allocation and prioritization
• Schedule and coordinate high-stakes meetings with investors, board members, and key industry partners, including preparation of briefing materials and follow-ups
• Plan and execute domestic and international travel arrangements, creating detailed itineraries to maximize the CEO’s time and effectiveness
• Drive special projects independently, from research and analysis to implementation
• Manage relationship dynamics with the internal leadership team and external stakeholders
• Prepare and review presentations, communications, and other materials for accuracy and alignment with company messaging
• Coordinate board meetings and maintain critical company documentation
• Anticipate needs and create systems to streamline operations and communication flows
• Plan and execute company events and offsites, ensuring seamless logistics, comms, vendor coordination, and scheduling
• 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
• 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

Benefits

• 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 our Warrior Manifesto