Chief of

Chief of Staff – Multi-Company Portfolio

Location:Remote – South Africa or Latin America preferredEmployment Type:Full-TimeIndustry:Multi-Industry / Entrepreneurial PortfolioReports 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
A large home care company with more than 100 employees
* Zenti, a payment processing business
Zenti, a payment processing business
* A roofing company
A roofing company
* An ATM business
An ATM business
* A reputation management company
A reputation management company
* Real estate holdings in Florida, including a co-living model
Real estate holdings in Florida, including a co-living model
* Additional entrepreneurial and investment interests
Additional entrepreneurial and investment interests
* A new real estate syndication podcast currently being launched
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 theEOS 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 approximately10–20 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 exceptionalChief of Staffto 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 anAI-enabled executive operatorwho 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
Key initiatives
* Outstanding decisions
Outstanding decisions
* Founder commitments
Founder commitments
* Business priorities
Business priorities
* Cross-company projects
Cross-company projects
* Follow-ups
Follow-ups
* Deadlines
Deadlines
* KPIs
KPIs
* Risks and blockers
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
What each company is focused on
* Its most important KPIs
Its most important KPIs
* Major projects currently underway
Major projects currently underway
* Where execution is falling behind
Where execution is falling behind
* Which issues require founder involvement
Which issues require fou