Founder’s Executive Assistant and Chief of Staff Apprentice

I am a founder operating several businesses involving agriculture, consumer products, e-commerce and professional services.

I am looking for a smart, dependable and highly organized assistant who can learn how I work and gradually become my trusted right hand.

You do not need extensive executive-assistant experience. I am looking for intelligence, character, curiosity, discretion, courage and exceptional follow-through.

Your Responsibilities
Organize messages, voice notes, email s and documents
Track commitments, deadlines and follow-ups
Manage calendar items and reminders
Research companies, vendors, products and services
Follow up with contractors, attorneys, accountants and vendors
Prepare short summaries of what happened and what must happen next
Organize Google Drive files and business records
Draft routine email s and messages
Record decisions and confirm they are carried out
Continue following up until each assignment is actually completed

You will not initially make business, product or financial decisions.

Your job is to organize the work surrounding those decisions and make sure nothing important is forgotten.

The Person I Am Looking For

You should be:

Intelligent and curious
Honest, moral and discreet
Highly organized
Persistent
Calm under pressure
Not easily intimidated in professional or business situations
Comfortable communicating with executives, attorneys, accountants, vendors and contractors
Able to respectfully speak your opinion
Willing to question something that appears dishonest, unethical, legally questionable or misleading
Willing to identify work that conflicts with the founder’s approved vision, voice or brand doctrine
Able to disagree respectfully rather than quietly allowing a bad decision or mistake to continue
Comfortable asking focused questions
Able to write clearly in English
Willing to learn unfamiliar subjects
Comfortable receiving direct feedback
Available full-time
Not currently working another full-time position

I do not want someone who agrees with everything simply because I am the founder.

I want someone who is loyal to the truth, the integrity of the businesses and the founder’s established direction.

You must be able to say:

“I do not believe this is accurate.”
“This does not appear consistent with the brand direction.”
“I think we may be overlooking a risk.”
“The contractor did not complete what was promised.”
“I believe this should be reviewed before we proceed.”

The right person will receive more responsibility and higher compensation as trust and capability are demonstrated.

No AI-Generated Applications

Your application must be written personally by you.

Do not use ChatGPT, Claude, Gemini or another AI tool to write, rewrite or polish your answers.

Applications will be reviewed for generic or AI-generated language. Only honest, personal responses will be considered.

Your English does not need to be perfect. Your answers need to be real.

How to Apply

Begin your application with:

READY TO LEARN

Then answer these questions in your own words:

Why are you interested in becoming a founder’s assistant?
Describe a time you were responsible for remembering and completing several different tasks.
Describe a time you respectfully disagreed with a manager, client or person in authority.
What would you do if you believed an instruction was dishonest, unethical or legally questionable?
What would you do if a contractor’s work did not match the founder’s approved vision or instructions?
What do you do when someone does not respond to an important request?
Describe a mistake you made and what you changed afterward.
What is something important you noticed that another person had missed?
How do you organize deadlines and follow-ups?
Are you comfortable handling confidential personal and business information?
What hours can you work?
Are you currently working for another client or employer?
Why did your most recent job end?

Attach your résumé and provide the contact information for one former manager or client who may be contacted as a reference.

I am looking for someone who becomes more useful every week, quietly notices what others miss, speaks honestly when something is wrong and completes what others leave unfinished.