Chief of Staff (Remote) - AI-Powered Operations for Online Education Company, Remote Job

Remote | Full-Time Preferred

About DAASS

DAASS is a US-based education company building high-quality professional academies and using technology, AI, and strong operational systems to scale how we work.

We are looking for an exceptional Chief of Staff to work closely with our CEO and help turn important ideas and company priorities into execution.

The Role

This is not an executive assistant role, and it is not a traditional project-management role.

We need someone who can be handed an objective, sometimes in an area they have never worked in before, and figure out how to move it forward.

Examples might include:

  • Leading the company's transition from one major technology platform to another

  • Researching and pursuing accreditation opportunities

  • Improving an operational system that is not working

  • Evaluating software, vendors, consultants, or new hires

  • Building an executive reporting or financial tracking system

  • Researching a new initiative and turning it into an actionable plan

  • Coordinating technical specialists without needing to personally be the engineer

  • Using AI to research, analyze, organize, troubleshoot, and move substantially faster

You will work closely with the CEO throughout the day and be trusted with important company initiatives.

The CEO will make consequential final decisions.

Your job is to make sure that by the time a decision reaches her, the problem has been properly understood, the options have been researched, the right questions have been asked, and execution is already moving.

We Are Looking for Someone Who:

  • Has unusually strong judgment and common sense

  • Thinks naturally in systems

  • Is highly organized and extremely dependable

  • Can take an ambiguous objective and create structure around it

  • Does not need constant instructions or follow-up

  • Is highly proficient with AI and uses it as a serious work tool

  • Is technically informed and comfortable understanding how software and systems fit together

  • Can intelligently hire and manage specialists in areas outside their own expertise

  • Is comfortable with numbers, budgets, spreadsheets, and business metrics

  • Can research unfamiliar subjects quickly without confusing AI output with verified fact

  • Communicates clearly and concisely

  • Knows when to make a decision independently and when something needs to come back to the CEO

  • Notices problems, inconsistencies, and risks before being asked

You do not need to already be an expert in Klaviyo, accreditation, accounting, or every platform we use.

In fact, one of the most important parts of this position is being able to enter an unfamiliar subject, understand it quickly, determine what expertise is required, and lead the initiative intelligently.

What Matters Most

We are looking for someone we can eventually say this to:
“Here is what we're trying to accomplish. Please run with it.”
And trust that it will not get lost, forgotten, or require the CEO to manage every step.

To apply, click the Apply Now button and fill out the Form.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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