SUMMARY
The Executive Assistant to the Chairman serves as a high-impact operator, systems builder, and trusted partner responsible for optimizing the Chairman’s time, workflows, and execution capacity across a diverse portfolio of businesses, investments, and initiatives. This role goes beyond traditional administrative support, acting as both an execution engine and an architect of AI-enabled systems that increase speed, leverage, and operational efficiency. The Executive Assistant will manage day-to-day priorities while designing and implementing automation, AI workflows, and process improvements that reduce manual work and streamline operations, maintaining an “automation-first” mindset at all times.
Operating in a fully remote, fast-paced environment, this individual will coordinate across multiple stakeholders, manage high volumes of information, and ensure seamless execution across both professional and select personal commitments. The ideal candidate is highly resourceful, technically fluent, and relentlessly proactive—capable of translating needs into systems and ensuring nothing stalls or falls through the cracks. This role is best suited for a highly intelligent, detail-oriented operator who thrives in ambiguity, embraces emerging technologies, and brings a disciplined, solutions-driven approach to improving how work gets done.
KEY RESPONSIBILITIES
Executive Support & AI-Augmented Workflow Management
- Manage and optimize the Chairman’s complex calendar, priorities, and commitments with a focus on efficiency and leverage
- Leverage AI tools (e.g., Claude and similar platforms) to automate scheduling, follow-ups, reminders, and task management
- Continuously identify opportunities to reduce manual intervention and improve responsiveness through automation
Technical Execution & AI Systems Development
- Design, build, and maintain AI-powered workflows and automations that streamline executive operations
- Utilize AI platforms (including Claude with coding capabilities) to create scripts, integrations, and systems that enhance productivity
- Continuously test and iterate on new AI tools to improve speed, accuracy, and scalability of support functions
Communication & Information Management
- Manage and draft high-level communications, leveraging AI to accelerate drafting, summarization, and response workflows
- Synthesize large volumes of information into concise, actionable insights and executive-ready summaries
- Maintain structured systems for organizing communications, documents, and knowledge
Meeting, Briefing & Follow-Through Management
- Capture key takeaways, decisions, and action items, ensuring clear ownership and follow-through
- Build systems to track deliverables, deadlines, and stakeholder accountability
- Automate recurring reporting and meeting preparation workflows where possible
Operational Efficiency & Process Optimization
- Audit existing workflows and identify inefficiencies, redundancies, and bottlenecks
- Implement systems, tools, and automations that improve execution speed and reduce friction
- Drive a culture of efficiency, responsiveness, and continuous improvement in how work is executed
Personal Support (as needed)
- Provide limited personal administrative support, applying the same systems-driven and efficiency-focused approach
- Ensure seamless integration of personal and professional scheduling and commitments where required
QUALIFICATIONS
- 5+ years of experience supporting a senior executive in a fast-paced, high-performance environment
- Demonstrated experience using AI tools—particularly Claude (including Claude Code) to automate workflows, build systems, and improve operational efficiency
- Strong technical fluency with modern productivity tools, automation platforms, and AI-enabled systems
- Exceptional organizational skills with the ability to manage complex, high-volume workflows
- Outstanding written and verbal communication skills with a polished, executive-level presence
- Strong problem-solving and analytical skills with the ability to synthesize complexity quickly
- Detail-oriented, highly reliable, and committed to execution excellence