Chief of Staff - Strategic Initiatives & AI Operations

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TYPE OF WORK

Full Time

SALARY

47,000-170000

HOURS PER WEEK

40

DATE UPDATED

Sep 4, 2026

JOB OVERVIEW

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.

Form: ----------

SKILL REQUIREMENT
Data Analytics Process Improvement AI Tools
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