Executive Assistant to CEO / Chief of Staff - Remote

Overview

TumblerWare is seeking a highly proactive and strategic Executive Assistant (EA) who has the potential to grow into a Chief of Staff role. This is not a conventional EA position—it requires a strong operational mindset, problem-solving skills, and the ability to drive initiatives independently. You will act as the CEO’s right hand, ensuring efficiency, structure, and execution across key business priorities.

In Short

• Serve as an operational partner to the CEO, managing high-priority action items and follow-ups.
• Oversee executive scheduling, meetings, and internal workflow efficiency.
• Implement and refine processes, automation tools, and project tracking systems (Asana, AI tools, dashboards).
• Act as a gatekeeper, ensuring alignment and prioritization of key initiatives.
• Conduct research, data synthesis, and due diligence to inform decision-making.
• Maintain real-time dashboards, tracking critical metrics and KPIs.
• Take structured meeting notes and translate them into actionable next steps.
• Organize and optimize internal documentation and knowledge management.
• Serve as a liaison between leadership, stakeholders, and external partners.
• Support hiring processes, candidate vetting, and onboarding procedures.

Requirements

• Highly Analytical & Proactive: Able to anticipate needs, identify gaps, and solve problems before they arise.
• Strong Operational Thinker: Can structure workflows, streamline systems, and drive execution.
• Adaptable & Comfortable with Ambiguity: Thrives in a fast-evolving environment with minimal hand-holding.
• Exceptional Communicator: Synthesizes complex information into clear, actionable updates.
• Tech-Savvy & Process-Oriented: Comfortable with automation, AI tools, dashboards, and operational software.
• High Ownership Mentality: Takes full accountability for results, not just effort.

Benefits

• This position is fully remote for anyone living in the United States.
• Some travel may be required for in-person collaboration.