Operations Executive / Chief Of Staff for US SaaS company (Remote)

About Paired

Paired is a global staffing and recruiting agency that specializes in pairing remote work with top-tier talent!

We are dedicated to connecting talented individuals with remarkable companies in need of their skills. Our goal is to create fulfilling job opportunities for professionals around the world.

About our Client

Our client is Richard Yu. He runs a fast-growing education and software business, and across their channels, his team and him, have built a platform of more than 1.5 million followers.

His job is to be the face of their content and to think about where the company goes next. That takes about forty hours a week of creating, plus long uninterrupted blocks for strategy. It leaves very little room for anything else.

Which is the problem. Projects need chasing. Follow-ups need sending. Hiring needs running. Reports need collecting. None of that happens on its own, and when he tries to do it, the content and the strategy suffer.

That is what this role is for. You'll protect his time, remove operational drag, and make sure the company actually executes.

The Role

A lot of roles with this title are a dead end: no access to the founder's inbox, no seat in the meetings, just a pile of disconnected projects nobody else wanted. If that is your experience of these jobs, he understands the scepticism.

This is not that. You will see his calendar, his inbox, his meetings, and his numbers. You will watch decisions get made in real time and understand why they went the way they did. Done properly, it is the fastest and most complete training in how to run a company that exists, which is why it comes with a defined path to Chief of Staff over twelve to eighteen months.

The trade is simple, and he would rather be blunt about it. You get total context. In exchange, you do the work he genuinely does not want to do: the chasing, the reminding, the coordinating, the collecting, the repetitive things that protect my creative bandwidth.

If that trade sounds good to you, keep reading. If you want the access without the admin, this is not your role.

What You'll Own

Calendar, first and above everything else

• Protect deep work blocks, batch meetings, enforce priorities
• Turn a chaotic week into an intentional one that matches company goals
• Gate my time, never my people. You are not a human shield and you will never intercept someone who should be talking to me directly

The follow-up engine

• Action items, owners, due dates, reminders, escalation
• Nothing dies in Slack, WhatsApp or email because somebody got busy
• Draft messages, emails and internal updates so I can approve them fast

Project management and accountability across the company

• Build and run the company operating system, whether that lives in Trello, Asana or Notion
• Every project carries an owner, a deadline, a next action and a definition of done
• Hold department leaders to what they committed to, including when that means a difficult conversation

Hiring operations

• Run hiring end to end for key roles: an Organic Content Director, a Senior DR Copywriter, an Instagram Copywriter and others
• Pipeline, scheduling, scorecards, assignments, Loom reviews, references
• Keep it moving fast without dragging me into logistics

Content operations oversight

• You will not create content. You will make sure it ships
• Track weekly output, deadlines and approvals across YouTube, Instagram and email so I am not chasing anyone

Metrics and reporting

• Collect and analyse the monthly P&L, maintain KPI dashboards, run the weekly reporting rhythm
• Review payroll, which means you will know what everyone earns, and come back with specific recommendations on raises, comp structure, inefficiency and where we are carrying people we should not be

Projects that do not fit anywhere else

• Sometimes real-world and operational, such as managing the build-out of a home studio in Puerto Rico
• Sometimes unglamorous. A real example: three or four hours going line by line through my AMEX statement to find software we are overpaying for, then contacting each vendor to cancel. The right answer is to do it once, then automate it, delegate it or own it monthly

AI across the workflow

• Using ChatGPT instead of Google is the floor, not the bar
• You should be good enough that you are advising other department leaders on how to use AI in their own work

How you will be trained

Nobody performs on day one in this role, and I do not expect you to. Context is the whole job, and context takes time to build.

• Weeks 1 to 4, shadowing. You sit in on everything: calendar, meetings, comms, priorities. You build your own model of how I think, what I care about and how I decide. You start taking small things off my plate immediately, mostly scheduling, notes and action items.
• Days 30 to 60, execution and systems. You take over the follow-up engine and the task system. You run a short structured weekly planning session with me. You start managing hiring operations and cross-functional projects, and you begin enforcing owners and due dates.
• Days 60 to 90, Office of the CEO. You run the operating cadence: reporting, follow-ups, meeting prep. You own major initiatives. You are my execution arm while I focus on content and strategy.
• Months 3 to 18, Chief of Staff track. As trust and competence compound, the work shifts from execution toward leverage: planning rhythms, decision memos, cross-functional problem solving, running high-priority initiatives. This is performance-based, not automatic.