Chief of Staff – Multi-Company Portfolio

Location: Remote – South Africa or Latin America preferred
Employment Type: Full-Time
Industry: Multi-Industry / Entrepreneurial Portfolio
Reports To: Founder & Owner

About the Founder & Business Portfolio

Our client is an experienced entrepreneur and multi-business owner based in Michigan, 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 large home care company with more than 100 employees
Zenti, a payment processing business
A roofing company
An ATM business
A reputation management company
Real estate holdings in Florida, including a co-living model
Additional entrepreneurial and investment interests
A new real estate syndication podcast currently being launched

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.

The Opportunity

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 approximately five core 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.

Key Responsibilities

Founder & Executive Operations

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.

Cross-Portfolio Coordination

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.

The Chief of Staff should 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

The goal is not to become the COO of every company, but rather to ensure that the founder's priorities are being executed throughout the portfolio.

KPI & Accountability Systems

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

The Chief of Staff should reduce the founder's need to manually chase people for updates.

Communication Management

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.

Project & Initiative Management

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-Enabled Executive Operations

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

The successful candidate should view AI as part of their everyday operating system rather than as an occasional productivity tool.

Executive Briefings & Decision Support

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

Rather than forwarding large amounts of raw information, synthesize what matters.

A strong briefing should communicate:

What happened?
Why does it matter?
What decision is needed?
What are the available options?
What is the recommended next step?

Process Improvement

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

The founder is specifically looking for someone who can identify a problem and propose a solution—not someone who simply reports that a problem exists.

Ideal Candidate

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?”

Qualifications & Experience

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

Key Competencies

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.

What Success Looks Like

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.

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