Yes, this starts as a job. But, ultimately, it’s an opportunity to collaborate with a seasoned founder on vastly greater things.

The Pitch

I’m a successful founder looking to transition from serial entrepreneurship (founding and scaling one company at a time) to portfolio entrepreneurship (non-operational partial-ownership in several businesses). I served as both visionary and integrator (the detail guy) in my last successful business. But what got me here won’t get me where I want to go.

You'll be joining me and an executive assistant who is already working for me. She is currently full up with both internal work and client work. Which is why we're looking for a second executive assistant.

I’m looking for a well-organized, detail-focused, growth-oriented individual who can rely on their years of experience to excel in the following three areas.

Executive Assistant: Meeting coordination, email maintenance, lightweight bookkeeping and invoicing, CRM maintenance, and travel management.

Outbound Sales Management: This is specific to this role. The first company we are launching is HighGrowth.io. It's a sales coaching and consulting practice. So I'm looking for someone who has at least a couple of years experience in outbound sales.

Chief of Staff: As I stated above, I’m looking to build out a portfolio of businesses. This will be accomplished through investment, acquisition and collaboration with like-minded entrepreneurs. I’ve identified multiple opportunities and I need someone to do the tactical and detail work but also collaborate with me as we identify and evaluate business opportunities. You’ll be the initial COS within one or more of the businesses. This role is not limited to COS but could grow into business operator responsibilities as the need arises (and assuming you have the desire).

In short, I’m looking for someone with proven EA and COS achievements, with outbound sales experience, and with a burning desire to elevate to the next level.

What Does Success Look Like?

Within 2025:

We have at least one business where I am active financially and as a visionary.
You will be engaged with me and my current EA on that business endeavor.
We are seriously pursuing a targeted list of three additional business endeavors.
By now, this will include a small group of experts who are assisting us. You may own all COS duties for this group.
You are automating or offloading some EA and other activities to further focus on ongoing sales management and/or COS activities.

Within three years:

We have at least three businesses where I am active financially and as a visionary.
At least one of those businesses has an annual recurring revenue over $5 million.
You are either serving as COS across some of those activities or you are operating one of them. Put another way, your EA, sales management and COS roles have grown to the point that we have hired one or more people to assist you -- you have chosen and are focusing on the activities from those roles that you are best at and most enjoy, and others have taken over the rest.
We are seriously pursuing a targeted list of three additional business endeavors (all bigger than the previous endeavors we have initiated).

Some Additional Details

This role is fully remote. I'm located in the Central European timezone and we will need at least five hours of overlap each day.

I'm open to part time or full time -- but at least 20 hours a week.

I rely heavily on Apple devices, applications and services. You will need to have a Mac for this job.

HighGrowth.io remote jobs

Senior Executive Assistant