Executive Operator to Chief of Staff Growth Track (12-18 months)

Executive Operations (Exec Ops) Chief of Staff Track, 12–18 Months)

If you’re a highly organized, extremely self-accountable, love project management (think Trello/Asana), and desire to grow into the 2nd in command of a fast growing startup… then this might just be your dream job.

My name is Richard Yu, I’m the founder/CEO of a fast-growing education + software business.

Across all social, my media team and I have built a 1.5M+ follower platform (@richardyuzee on IG, as an example).

My #1 responsibility is to spend 40 hours/week being the talent (face of our content), and visionary (having long blocks of 4 hrs/day) where I can think about vision and growth strategies.

That means I need to spend all my time creating content, driving strategy, and making high-leverage decisions… and this is where you come in.

Your job is to protect my time, eliminate operational drag, and make sure the company actually executes.

This role is Exec Ops / Office of the CEO — think of it as a supercharged Executive Assistant with a real path to Chief of Staff, based on performance. You will be my execution arm and second brain, with high trust, high access, and high expectations.

This is not a “cute admin” job. It’s also not a glamorous strategy-only job. It’s the real work: calendar, follow-ups, accountability, systems, project management, hiring ops, and getting things done

What you’ll own (your responsibilities)

1) CEO Time + Calendar (your #1 responsibility)

• Own my calendar ruthlessly: protect deep work blocks, batch meetings, enforce priorities
• Gate time, not people (you’re not allowed to be a “gatekeeper” personality)
• Turn chaos into an intentional weekly schedule that matches company goals

2) Internal Communication + Follow-Up

• Run the follow-up engine: action items, owners, due dates, reminders, escalation
• Ensure nothing dies in Slack/WhatsApp/email because people “got busy”
• Draft messages/emails and internal updates so I can approve quickly

3) Project Management + Accountability (across the whole org)

• Build/quarterback the company operating system (Trello/Asana/Notion—whatever we standardize)
• Every project has: owner, deadline, next action, definition of done
• Hold leaders accountable (ex: Moe accountable to deliverables, Bashar accountable to reporting cadence, content team accountable to output)

4) Hiring Operations (big focus right now)

• Run end-to-end hiring ops for key roles: Organic Content Director, Senior DR Copywriter/Head of Marketing, IG Copywriter, etc.
• Manage pipeline, scheduling, scorecards, assignments, Loom reviews, references
• Keep the process moving fast without me getting dragged into logistics

5) Content Operations Oversight (not creating content)

• Ensure content machines ship on time: YouTube, IG, email—whatever is on the calendar gets done on time.
• Track weekly output + deadlines + approvals so I’m not chasing people
• You must be insanely detail oriented and VERY good at calling people out and holding them accountable.

6) Metrics + Reporting

• Monthly P&L request/collection, KPI dashboards, and weekly reporting rhythm
• You will analyze the Profit & Loss statement every month, analyze the payroll (yes you will know how much everyone gets paid), and provide extremely detailed recommendations on who should get raises, comp structure adjustments, who is being inefficient, who needs to get cut, etc.

7) Personal + Local Projects (as needed)

• Help execute real-life projects that support business performance (ex: managing the build-out of a home studio in Puerto Rico)
• Spanish is preferred because it helps with local execution, but it’s not required. If you’re insanely quick with a translator / ChatGPT for messages, works as well.

8) AI Emphasis

• You should come with batteries included with understanding how to use AI in your workflow. The most BASIC version of this is ChatGPT instead of using Google, that’s the bare bare minimum.
• You should be so good with AI that you are now giving feedback and suggestions to OTHER department leaders on how they should be using AI in their day to day responsiblities.

What success looks like (KPIs)

• 20+ hours/week of my time returned within 60–90 days
• I stop doing: project management, follow-ups, DM appointment setting, internal chasing, hiring logistics
• Weekly operating rhythm runs without me pushing it
• Projects move faster, less stress, fewer dropped balls
• The company becomes calmer and more accountable — not more chaotic

Who this is for

This is for you if:

• You’re an operator: you love execution, structure, and turning chaos into order
• You have extreme ownership: you don’t wait to be told, you anticipate
• You can make good decisions without asking me every day for permission.
• You’re comfortable being in the background while I’m front-facing in the content
• You’re discreet and trustworthy (you will see everything)
• You’re strong at writing and communication (VERY detailed reports, clear, direct)
• You enjoy running a tight system and holding people accountable

Who this is NOT for

This is not for you if:

• You want a “strategy-only” role where you get to “bounce ideas” with Richard without doing admin, follow-ups, or nitty-gritty execution
• You need constant direction, reassurance, or step-by-step instructions where you get “coaching” from Richard (FYI - you’re here to protect my time, not get “free mentorship” from Richard).
• You avoid conflict and can’t hold people accountable in tough conversations when they’re late or underperforming
• You’re not comfortable with high access + high confidentiality
• You get offended by doing “unsexy” tasks — this role includes them.
• Example: 3-4 hour project of looking at every single expense item on Richard’s AMEX credit card statement to identify for software and expenses that we are overpaying on, and then reaching out to each software company to cancel them.
• You should be smart to DO IT ONCE, and either build a system to automate this, delegate to someone else, or you just own this ongoing monthly moving forward.

The truth: the trade-off (good, bad, and ugly)

You will get full context: you’ll see my schedule, meetings, priorities, and how decisions get made in real time. This is high-speed CEO training.

In exchange, you will also do the work I genuinely don’t want to do:

• Following up, reminding, pushing projects forward
• coordinating hiring logistics and keeping candidates moving along by messaging them on iMessage and Whatsapp on my behalf
• Collecting metrics, reports, and making sure people deliver
• Dealing with repetitive tasks that protect my creative bandwidth

If that trade-off excites you, you’ll love this role.

Ramp / onboarding plan (how you’ll get trained)

Phase 1 — Shadowing + Context (Weeks 1–4)

• You shadow everything: calendar, meetings, comms, priorities
• You build the “Richard OS”: how I think, what matters, how I decide
• You start taking small tasks immediately (scheduling, notes, action items)

Phase 2 — Execution + Systems (Days 30–60)

• You take ownership of the follow-up engine + task system
• You run weekly planning with me (short, structured)
• You begin managing hiring ops and key cross-functional projects
• You enforce owners/due dates and begin reducing my stress load

Phase 3 — Office of the CEO Operator (Days 60–90)

• You run the operating cadence: reporting, follow-ups, meeting prep
• You manage major initiatives (ex: studio build, hiring, IP1 execution support)
• You act as my internal execution arm while I focus on content + strategy

CoS Track (Months 3–18, performance-based)

• As trust and competence compound, you move from “execution” into “chief of staff” style leverage: planning rhythms, decision memos, cross-functional problem solving, running high-priority initiatives.

Logistics

• Remote with strong overlap with my working hours (EST hours)
• Spanish preferred (not required)
• Tools: Google Workspace, Slack, Trello/Asana, Calendly, Zoom, Loom
• You must be comfortable with high confidentiality and sensitive information

Compensation (guidance)

Depends on seniority and location. As a guideline:

• Mid-level Exec Ops (EA → CoS track): ~$60K–$100K base + performance bonus
• More Senior Operator: ~$120K–$170K base + performance bonus
  We care more about performance, trust, and output than “years.”

Application Questions (Workable form)

Use these as your fields/questions:

1. Full Name
2. Email
3. Phone number + WhatsApp (if applicable)
4. Current location + time zone
5. LinkedIn URL
6. Resume upload (PDF)
7. Are you fluent in Spanish, Optional and preferred? (Yes/No / Conversational / Fluent)
8. What type of role are you aiming for in 12–24 months?
• (A) Long-term Exec Ops / EA to CEO
• (B) Chief of Staff track
• (C) Department leader (Ops/COO-type path)
• (D) Not sure yet
9. Loom Video Submission (required, 5 minutes, camera ON)

• Upload link (must be public/unlisted)

Record a 5-minute Loom with your camera on. Title it: “Exec Ops — [Your Name]”. In your video, answer:

1. Why this role, and why work for me, Richard?
2. You will be doing a lot of operational, project management, and high accountability work that Richard does NOT want to do. What about this trade-off excites you?
3. Tell me about the HARDEST problem you solved supporting a CEO/Founder. What was the situation, what did you do, and what was the result?
4. How do you run follow-ups and accountability without being annoying? Give your approach/system.
5. What are your non-negotiables and dealbreakers? Be honest
6. Title the video of the loom: “YOUR NAME - Peanut Butter” (let’s see your attention to detail here). YT videos not accepted, only loom.

Final Assignment:

Read this google document and watch all the embedded YT videos inside of it (there are 3-4 videos in the google doc).

This is written by CEO Coach Matt Mochary (Business Coach to multiple billionaire companies currently), and Richard learns directly from him.

After reading this google doc and watching the videos inside, explain in 3-5 sentences minimum WHY you would thrive and do extremely well in this role?

LINK: https://docs.google.com/document/d/1-tcubUwvktoV-Ou3bB6ynk2LLwNzdT3D_p_ILreyR_A/edit?tab=t.0