Chief of Staff - 21335

Location: Remote

Employment Type: Full-Time

Industry: Multi-Industry / Entrepreneurial Portfolio

Reports To: Founder & Owner

Our client is an experienced entrepreneur and multi-business owner who has built and operates a diverse portfolio of companies and investments across several industries.

Rather than operating a single traditional company, the founder oversees a collection of businesses that currently includes a variety of service-based businesses, real estate holdings, passive income operations, and investment ventures.

The founder operates primarily as a visionary. His strength lies in identifying opportunities, creating businesses, developing strategy, forming partnerships, and driving growth rather than managing every detail of day-to-day execution.

His preferred organizational model is similar to the EOS Visionary/Integrator structure. Where possible, individual companies have strong operators or COOs responsible for daily execution, allowing the founder to remain focused on vision and strategy.

One of the portfolio businesses already has a highly capable COO, demonstrating the operating structure the founder ultimately wants across his companies.

As the portfolio has expanded, however, the volume of communication, decisions, priorities, projects, and follow-ups reaching the founder has become increasingly difficult for one person to manage.

The founder's long-term goal is to reduce his operational involvement to approximately 10–20 hours per week, allowing him to remain focused on high-value strategic work without having to constantly monitor whether projects, people, and commitments are moving forward.

We are seeking an exceptional Chief of Staff to become the founder's right hand across his portfolio of businesses.

This is not a traditional Executive Assistant position.

The successful candidate will function as an AI-enabled executive operator who helps the founder manage the operating “machine” surrounding him.

The Chief of Staff will sit between the founder's vision and the execution occurring across core portfolio businesses, ensuring that priorities are translated into action, KPIs remain visible, commitments are followed through, and important information does not disappear across multiple communication channels.

The founder currently receives communication from employees, clients, business partners, operators, and other stakeholders across several companies. Information is fragmented across multiple inboxes and channels, creating a legitimate risk that important tasks, commitments, or issues may be missed.

The Chief of Staff will create order around this complexity.

Rather than waiting for the founder to manually follow up on every conversation or initiative, this person will proactively identify what needs attention, determine who owns it, ensure progress is being made, and escalate only what genuinely requires the founder's involvement.

• Serve as the founder's primary operational right hand across his portfolio.

• Translate ideas, conversations, strategic priorities, and founder directives into clearly defined actions.

• Maintain visibility over:

  • Key initiatives

  • Outstanding decisions

  • Founder commitments

  • Business priorities

  • Cross-company projects

  • Follow-ups

  • Deadlines

  • KPIs

  • Risks and blockers

• Ensure that when the founder says something needs to happen, there is a clear owner, deadline, and follow-through mechanism attached to it.

• Maintain a high-level understanding of what is happening across the founder's various companies.

• Interface with COOs, operators, managers, and key team members without unnecessarily inserting the founder into day-to-day operations.

• Understand:

  • What each company is focused on

  • Its most important KPIs

  • Major projects currently underway

  • Where execution is falling behind

  • Which issues require founder involvement

  • Which issues can be resolved without him

• Ensure that the founder's priorities are being executed throughout the portfolio without serving as the direct COO for every individual entity.

• Help establish and maintain clear KPI dashboards and accountability systems across the portfolio.

• Work with company leaders to identify the metrics that matter most and ensure they are consistently tracked and reported.

• Create an executive-level view that allows the founder to quickly understand:

  • Business performance

  • Progress against priorities

  • Emerging problems

  • Missed commitments

  • Operational risks

  • Areas requiring strategic decisions

• Reduce the founder's need to manually chase people for updates.

• Create structure around the high volume of inbound communication reaching the founder.

• Help organize and prioritize communication from:

  • Employees

  • Company leaders

  • Customers

  • Business partners

  • Vendors

  • Investors and professional contacts

  • Other stakeholders

• Identify what genuinely requires the founder's attention versus what can be delegated, answered, routed, or handled independently.

• Ensure important conversations result in documented actions and follow-ups.

• Track strategic projects across the portfolio from concept through completion.

• For each initiative, establish:

  • Objective

  • Owner

  • Deliverables

  • Timeline

  • Dependencies

  • KPIs

  • Next actions

• Proactively follow up with responsible parties and identify stalled initiatives before the founder has to intervene.

• AI capability is a central requirement for this position.

• The founder personally uses AI extensively and specifically does not want an “old-school” assistant who simply performs administrative work manually.

• The Chief of Staff should naturally look for ways to use AI to:

  • Summarize communications

  • Extract action items

  • Prepare executive briefings

  • Organize information

  • Draft responses

  • Track decisions

  • Research opportunities

  • Improve workflows

  • Automate repetitive tasks

  • Create dashboards and reporting

  • Improve personal and organizational productivity

• View AI as part of an everyday operating system rather than as an occasional productivity tool.

• Provide concise, structured updates to the founder so he can make decisions quickly.

• Synthesize what matters rather than forwarding large amounts of raw information.

• Ensure briefings communicate:

  • What happened?

  • Why does it matter?

  • What decision is needed?

  • What are the available options?

  • What is the recommended next step?

• Identify recurring areas of friction across the founder's workflow and recommend better systems.

• Proactively identify problems and propose actionable solutions.

The ideal candidate is an unusually proactive operator who thrives in entrepreneurial environments.

You are comfortable working with a founder whose attention may move rapidly between companies, ideas, opportunities, and strategic initiatives.

You do not need every process documented before beginning work; instead, you create structure where structure is missing.

You naturally think: “What needs to happen next, who needs to own it, and how do I make sure it gets done?”

• Previous experience as a Chief of Staff, Executive Operations Manager, Senior Executive Assistant, Business Operations Manager, or similar role.

• Experience directly supporting a founder, CEO, entrepreneur, or multi-business owner.

• Strong project and program management capability.

• Demonstrated ability to manage multiple priorities simultaneously.

• Strong understanding of KPIs and executive reporting.

• Experience coordinating across multiple teams or business units.

• Highly proficient with modern AI tools (experience creating AI-enabled workflows is strongly preferred).

• Excellent written and spoken English.

• Strong business judgment.

• Exceptional organization and follow-through.

• Extreme ownership: If something has been assigned, you ensure it reaches completion.

• High initiative: You identify what needs doing without waiting for instructions.

• AI-native thinking: You instinctively consider how AI can improve the way work gets done.

• Business acumen: You understand how businesses operate beyond administrative tasks.

• Executive judgment: You know what requires the founder's attention and what does not.

• Comfort with ambiguity: You can operate effectively without a detailed playbook.

• Solution orientation: Problems should arrive with proposed solutions.

• Communication: You can confidently interact with senior leaders and company operators.

• Accountability: You are comfortable following up repeatedly until commitments are fulfilled.

Within the first several months, the founder should feel significantly less operationally overloaded.

He should have confidence that:

• Nothing important is falling through the cracks

• His commitments are tracked

• Business leaders are being held accountable

• KPIs are visible

• Projects are moving

• Communication is organized

• Important issues reach him quickly

• Low-value issues do not require his attention

• AI is being used to increase efficiency

• His ideas are consistently converted into execution

Ultimately, the Chief of Staff will help enable the founder to operate primarily as a visionary while maintaining confidence that the execution engine behind his portfolio is functioning effectively.