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Chief of Staff to the Chairman

Remote

SUMMARY

The Chief of Staff serves as the Chairman’s strategic partner, operational anchor, and execution engine across a wide portfolio of businesses, investments, and new ventures. This role supports the Chairman’s highest priorities by driving clarity, velocity, and alignment across projects, ensuring that vision is consistently translated into action. The Chief of Staff will streamline decision-making, manage complex multi-stakeholder initiatives, oversee information flow, and proactively remove barriers so the Chairman can operate at maximum impact. This position also includes managing select personal scheduling, meetings, and commitments to protect the Chairman’s time and enable focus.

This role is responsible for driving high-priority AI-enabled initiatives from concept through outcome. This role will operate as a systems builder and execution driver—owning complex, cross-functional initiatives end-to-end, accelerating engineering velocity, and enforcing a culture of urgency and accountability. The ideal candidate translates vision into systems, pushes teams to ship at speed, and maintains an “always-on” posture to ensure momentum never stalls. This role requires strong technical fluency, experience implementing AI-enabled workflows, and the confidence to hold senior contributors accountable without hesitation.

It is ideal for a highly intelligent, resourceful operator who thrives in a fast-paced environment, navigates ambiguity with confidence, and brings a disciplined, solutions-oriented approach to every challenge.

KEY RESPONSIBILITIES

Strategic Partnership

  • Serve as a trusted advisor and thought partner to the Chairman, helping shape priorities, evaluate opportunities, and support informed decision-making across businesses and projects.
  • Translate high-level vision into clear plans, timelines, structures, and next steps that drive measurable progress.
  • Anticipate needs, identify blind spots, and proactively surface insights or recommendations to keep initiatives on track.

Technical Execution & AI Systems Delivery

  • Lead AI-enabled initiatives from concept to live deployment, ensuring measurable business impact.
  • Design, prototype, and implement AI workflows, automation systems, and operational tools that increase leverage and speed across ventures. 

Operational Leadership

  • Implement systems, processes, and tools that improve workflow, eliminate inefficiencies, and optimize the Chairman’s time.
  • Oversee information flow to and from the Chairman, ensuring the right inputs reach the right people at the right moment.
  • Establish operating rhythms, including dashboards, reviews, reporting structures, and communication cadences across ventures.

Project and Venture Management

  • Establish aggressive execution timelines and hold teams accountable to them.
  • Drive a high-urgency operating cadence with tight feedback loops, clear ownership, and minimal bureaucracy.
  • Escalate risks immediately and directly when deliverables or response times fall short.
  • Lead high-impact projects from concept through execution, coordinating across teams, partners, and external vendors.
  • Manage special initiatives related to new business development, investment diligence, strategic partnerships, and corporate innovation.
  • Track progress, risks, deliverables, and KPIs, ensuring alignment with the Chairman’s goals and expectations.

Stakeholder and Relationship Management

  • Act as an extension of the Chairman in select meetings, communications, and negotiations, ensuring seamless representation and continuity.
  • Prepare briefs, talking points, memos, and follow-ups for internal and external engagements.
  • Help maintain and strengthen relationships with senior executives, partners, investors, boards, founders, and strategic collaborators.

Communications and Analysis

  • Produce executive-level summaries, recommendations, presentations, and research that support strategic choices.
  • Synthesize information across businesses, markets, and teams into concise, actionable insights.
  • Drive follow-through to ensure decisions become outcomes.

QUALIFICATIONS

  • Bachelor’s degree in Business, Communications, Public Policy, or a related field; advanced degree preferred.
  • 7 to 12 years of experience supporting a senior executive, founder, principal, or chairman across multiple ventures or a complex operating environment.
  • Demonstrated experience building or implementing real AI workflows, automation systems, or AI-enabled operational tools—not just experimentation or prompt usage.
  • Proven record operating as a strategic generalist and project leader with exceptional judgment.
  • Ability to thrive in a fast-moving, entrepreneurial environment with shifting priorities.
  • Exceptional written and verbal communication skills with a polished, executive presence.
  • Highly organized, detail-intensive, and able to manage complex workflows across many concurrent initiatives.
  • Strong analytical and problem-solving skills with the ability to synthesize complexity quickly.
  • 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 unflappable under pressure.

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