Chief of Staff, Chairman

This is a fully remote position, open to applicants in United States.

📋 Description

• Act as a trusted advisor and thought partner to the Chairman, assisting in shaping priorities, evaluating opportunities, and facilitating informed decision-making across various businesses and projects.

• Convert high-level vision into actionable plans, timelines, structures, and next steps that drive measurable results.

• Anticipate needs, recognize blind spots, and proactively present insights or recommendations to ensure initiatives remain on track.

• Lead AI-driven initiatives from inception to live deployment, guaranteeing measurable business outcomes.

• Design, prototype, and implement AI workflows, automation systems, and operational tools that enhance leverage and speed across ventures.

• Establish systems, processes, and tools that streamline workflow, eliminate inefficiencies, and optimize the Chairman’s time.

• Manage the flow of information to and from the Chairman, ensuring the appropriate inputs reach the right individuals at the right time.

• Create operating rhythms, including dashboards, reviews, reporting structures, and communication cadences across ventures.

• Set ambitious execution timelines and hold teams accountable for meeting them.

• Foster a high-urgency operating rhythm with tight feedback loops, clear ownership, and minimal bureaucracy.

• Promptly escalate risks when deliverables or response times do not meet expectations.

• Oversee high-impact projects from concept to execution, coordinating efforts across teams, partners, and external vendors.

• Manage special initiatives related to new business development, investment diligence, strategic partnerships, and corporate innovation.

• Monitor progress, risks, deliverables, and KPIs to ensure alignment with the Chairman’s objectives and expectations.

• Represent the Chairman in select meetings, communications, and negotiations, ensuring seamless representation and continuity.

• Draft briefs, talking points, memos, and follow-ups for both internal and external engagements.

• Assist in maintaining and enhancing relationships with senior executives, partners, investors, boards, founders, and strategic collaborators.

• Create executive-level summaries, recommendations, presentations, and research that inform strategic decisions.

• Integrate information across businesses, markets, and teams into concise, actionable insights.

• Ensure follow-through to convert decisions into tangible outcomes.

⛳️ Requirements

• Bachelor’s degree in Business, Communications, Public Policy, or a related field; advanced degree is preferred.

• 7 to 12 years of experience supporting a senior executive, founder, principal, or chairman in multiple ventures or a complex operating environment.

• Proven experience in building or implementing genuine AI workflows, automation systems, or AI-enabled operational tools—not merely experimentation or prompt usage.

• Established track record as a strategic generalist and project leader with outstanding judgment.

• Capability to excel in a fast-paced, entrepreneurial environment with changing priorities.

• Exceptional written and verbal communication skills, complemented by a polished, executive presence.

• Highly organized, detail-oriented, and adept at managing complex workflows across numerous concurrent initiatives.

• Strong analytical and problem-solving skills with the ability to quickly synthesize complex information.

• High integrity, emotional intelligence, and discretion in all interactions.

• Advanced proficiency in productivity platforms, project management tools, and modern tech solutions that enhance executive efficiency.

• Resourceful, proactive, and composed under pressure.

🏝️ Benefits

• Competitive salary and performance-based bonuses.

• Comprehensive health, dental, and vision insurance.

• Opportunities for professional development and continuous learning.

• Flexible work arrangements and a supportive work environment.