Simplero: Executive Assistant

Full-time. Remote. Pacific Time strongly preferred. Los Angeles county would be a huge bonus so we can be in person when it makes sense.

I’m looking for someone who genuinely loves being an Executive Assistant.

Someone who gets real satisfaction from bringing order to chaos, building systems that make life easier, and being the person behind the scenes who makes everything run smoothly.

When I’m able to stay in my zone of genius because you’ve already thought three steps ahead, that’s a great day for both of us.

If your favorite feeling is making other people more effective, keep reading.

The role

You love to move fast. You can handle a lot of ideas being thrown at you and know not to run with every last thing that gets thrown out there. You think. Ask questions. Use judgment.

I need someone who enjoys bringing structure to that without slowing it down.

Someone who’s willing to challenge me when it matters.

You’ll ask great questions. You’ll notice when I’m getting pulled in too many directions. You’ll remind me what I said was important. You’ll tell me when something doesn’t feel aligned or when you think I’m missing something.

I’m not looking for someone who just takes orders. I’m looking for a thought partner who helps me stay focused on what matters most.

What you’ll actually do

This isn’t just about managing my calendar or booking flights.

It’s about becoming my co-pilot.

You’ll own the operational and logistical side of my world so I can stay focused on creating, teaching, building, and leading.

That includes things like:

• Helping run live events and making sure everything is ready before I walk into the room

• Working with the team to solve problems instead of waiting for someone else to own them

• Building SOPs, systems, and documentation that make everything run more smoothly

• Researching whatever needs researching until you know enough to make great decisions

• Hiring and coordinating contractors and vendors

• Constantly asking, “How can we make this simpler? Better? Easier?”

• And yes: managing my calendar, inboxes, travel, and logistics

You’re the kind of person who…

• sees something that’s messy and instinctively starts organizing it.

• doesn’t wait to be asked.

• don’t need a detailed checklist.

• figure things out.

• build systems.

• make things better.

• love learning. If you don’t know something, you teach yourself. AI is your friend. 

• ask questions. You experiment. You document what works.

You’re confident enough to push back when you think I’m wrong, but humble enough to change your mind when you learn something new.

The more you can take off my plate, the more I get to do the work that only I can do.

This is a partnership.

I want someone who genuinely enjoys being the person behind the scenes making everything work.

Someone who gets excited when the machine runs beautifully.

Someone who loves helping another person do their best work.

If you get energy from making your person more effective, you’ll love this role.

To apply, record a 60-second video and tell my current EA:

1. What drew you to this role.

2. Tell me about a time you stepped into chaos and made it run smoothly.

3. Why you’d be an exceptional co-pilot.

4. Your compensation expectations.