Open Role · Remote · 2+ Years Supporting a Principal Required

Chief of Staff
(Personal)

Ravi does only the things that only Ravi can do. You own everything else in his life — the weekends, the travel, the projects, the house, the people who make it run. He shows up; you've already decided.

30 min
Of Ravi's Week, Max
2+ yrs
Running a Principal's Life
5 hrs
Daily Overlap, US Central
Wed 5 PM
Saturday Plan Delivered

Section 01

Who You'll Work For

Ravi Abuvala, 32. Founder of Scaling With Systems — a marketing and sales-systems company that has served 3,000+ clients and done $35M+ in revenue — with a 26-person remote team and a daily YouTube channel. Based on 30A in the Florida panhandle, frequently in Miami, increasingly in Europe with his team. One dog, Lua. Trains daily, doesn't drink, runs his life the way he runs his business: as a system.

What's Already Systemized

Meals are cooked for him by an in-person House Manager. The sauna turns itself on. The calendar defends his deep-work blocks. He journals every morning and reads a written set of principles. He has removed as many daily decisions from his life as one person can remove alone.

Where It Still Leaks

A 20-minute camera setup in a hotel room. An hour choosing a hotel. A Saturday that didn't get planned. A project that's been "in progress" since July. His team waiting days on a login only he can provide. Each one is small. Together they're the difference between building and managing. Your job is to make them go to zero.

The House Manager

An in-person House Manager runs the physical side of the house — cooking, the dog, laundry, deliveries, contractors at the door. You'll manage the House Manager's weekly list so that Ravi is never again the one asking. You don't replace them; you direct them.

The Business Team

Ravi has a leadership team, account managers, a sales team, and a content team. You do not run the business. You run the person who runs the business — and you're the reason his team can reach him in minutes instead of days.

Section 02

What You'll Own

Nine areas. Every one of them has an owner, a next step, and a date — and the owner is you.

Primary
The Board, and the House Manager

Ravi's personal task board (Asana) has 100+ open items and currently moves only when he's standing there driving it. You take it over on day one. You curate it, prioritize it, kill what's dead, and drive it whether Ravi is home, in Miami, or in Lisbon. You run the House Manager's weekly list.

Primary
Weekends and Fun

Saturday is built by Wednesday. Ravi's best days follow a formula — friends, activities all day, him as host — and you run it: the boat day, who's coming, the dinner after, the car, the backup if it rains. You keep a rotating list of his people and make sure he sees them. You know what he likes, and you book it without asking.

Travel
Travel, End to End

The standard: Ravi decides on Thursday he wants to be in Miami Friday, and everything else just happens. Car to the airport. A hotel that knows him (hotels over rentals, always). Gym, sauna, and meals sorted on arrival. A standing go-bag and packing checklist that you maintain and the House Manager executes, so he never thinks about packing. Tripod, light, adapters, and a desk arranged so they're waiting when he sits down. Everything above is done from wherever you are; if you're able to travel with him occasionally, that's a plus.

Primary
Personal Social Calendar

You run it end to end. Ravi tells you who he wants to see — or you suggest it from the rotating list — and you handle the outreach, the invitation, the timing, the reservation, the car, the flowers, and the confirmation on his behalf. You maintain a small playbook of pre-built evenings so a plan is one word from him to you. All he does is show up.

Projects
Projects

A dock build (HOA approval, permits, contractor). An interior designer engagement. A storage unit to consolidate and clear. Vehicle and equipment purchases and sales. Several financial close-outs currently sitting with a broker, a lender, and his family office. You own the timeline and the follow-ups; Ravi hears about it when it's done or when he's needed.

Ops
Reachability

Ravi is intentionally hard to reach. You are easy to reach. You hold the shared vault so his team gets what they need in seconds, not days. You triage his texts and Slack so the two things that actually need him reach him and the forty that don't, don't.

Ops
Money Admin

Bills, subscriptions, price increases, reimbursements, the digital mailbox, and the working relationship with his family office. You surface, you prepare, you chase. You do not make investment or spending decisions — those are his, and there's a written framework for them.

Ops
Health Logistics

Weekly stretch and massage bookings. Prescription and supplement reorders so nothing runs out. Doctor and dentist scheduling. The travel med kit when he flies.

Leverage
Your Own AI Leverage

Ravi's business runs on Claude Code. His personal systems — the voice-to-task intake for the board, the sauna automation, the financial planner — were built the same way, in hours. You're expected to use AI every day, and to build small systems that remove recurring work from your plate and his without being asked. A Chief of Staff who can set up an automation alone gets roughly three times as much done as one who can't. We'll ask what you've built.

What you do not own: cooking, cleaning, the dog, and physical work at the house (the House Manager). The business (a team exists). Filming or producing content.

Section 03

What a Real Week Looks Like

Not hypothetical. This is assembled from what's actually been on the board in the last 30 days.

M
Monday — the only 30 minutes you get

Your one call with Ravi. You come with decisions, not questions: the week's plan, three things you need a yes on, anything slipping. Afterward you update the board, brief the House Manager on their week, and chase the two vendors who went quiet over the weekend.

T
Tuesday — projects move

The handyman's quote for the railing and baseboards comes back; you approve it inside your authority and schedule him. The boat broker still hasn't confirmed the inspection date — you call, not email. The storage-unit consolidation gets a date and a hauler. You confirm Thursday's appointments.

W
Wednesday — Saturday is done

By 5 PM Ravi has one text from you: Saturday's plan, under 120 words. Boat at 11, six friends confirmed, dinner at 7, car booked, rain plan attached. He replies "yes." You also send the invite to the friends, pre-confirm Friday's calendar, and order the supplement refill that runs out in nine days.

T
Thursday — the curveball

At 4 PM: "Miami tomorrow through Sunday." Within an hour: car to the airport at 6:30 AM, hotel that knows him, gym and sauna access confirmed, dinner reservations for two nights, House Manager briefed on the dog and the go-bag. He gets one message with the plan. Nothing else.

F
Friday — close-out

One async message to Ravi: what shipped, what's blocked, what rolls to next week. The stretch therapist is booked for the next four weeks. Sunday dinner with his mom is on the calendar and the restaurant is confirmed. You log off knowing Saturday will run without you.

Real one-offs from the last 30 days
  • Book dinners, a train, a club, and a boat charter in Lisbon for a six-person team night — from the US, same day
  • Order a 30-day pill organizer and pack a month of vitamins for a trip abroad; source a travel cooler for a refrigerated prescription
  • Get a signet ring repaired and resized at a specific jeweler; extend a gold chain at another
  • Find a heavy-duty storage bag for life jackets on a small boat
  • List a standing desk and a bookshelf on Marketplace; sell a microwave
  • Get a contractor to core-drill four drain holes and install stainless mesh covers
  • Rescan and frame a newspaper article about his late father at 600 DPI
  • Resolve a grocery-delivery account locked behind a dead social login
  • Get a registration copy for a small boat; schedule yard cleanup and new pine straw for late September
Recurring, every week
  • Monday call; Friday close-out
  • Confirm Monday's and Thursday's appointments the business day before
  • Saturday plan delivered by Wednesday 5 PM
  • The House Manager's weekly list, reviewed and prioritized
  • Digital mailbox checked; anything important escalated same day
  • Every vendor who hasn't replied in 48 hours gets chased without anyone telling you
  • Board hygiene: nothing overdue without a note, nothing done left unmarked
  • Bi-weekly: stretch or massage booked; supplement inventory checked

Section 04

How You Make Decisions

Three rules. They're the whole job.

Rule 01
Decide. Don't Option.

If you send Ravi three choices, you've handed him the work back. Send one decision with a one-line reason. He can veto in one word. If you're wrong, you'll hear it once and adjust. If you're indecisive, you'll hear it twice.

Rule 02
Spend Inside Your Lane

Up to $1,000 per item and $3,000 per week inside your areas without asking. Above that, one message with the number and the reason. Pre-approved recurring items don't count. Nobody here nitpicks a good call.

Rule 03
Speed Without Slop

Acknowledged within two hours. Moving within 24. Closed within five business days. If something is going to slip, Ravi hears it from you before he notices — with the new date, not an apology.

The culture in one line: speed of execution without compromising accuracy, extreme ownership, and simplification. Those are the company's values and they're the filter for this role too.

Section 05

Who This Role Is For

This is not a first assistant job. We're looking for someone who has already run the life of a founder, an executive, or a private family — and was good enough at it that they got bored of being asked.

You're a fit if
  • You have 2+ years as a Chief of Staff, Executive or Personal Assistant, or Household/Estate Manager to a founder, executive, or private family — where you owned outcomes, not tasks
  • You have taste. You can pick the restaurant, the hotel, the gift, and be right
  • You close loops. A vendor who doesn't answer in two days gets a follow-up without anyone telling you
  • You write crisply and you're comfortable on the phone with American vendors, hotels, and contractors
  • You've run travel end-to-end — multi-city, short notice, someone else's preferences — and it went well
  • You're discreet to the point of being boring about it. You'll know his finances, his health, his personal life, and his family. None of it leaves
  • You like a founder's communication style: short messages, fast decisions, no meeting that could be a text
  • You'd rather be paid well to make things happen than paid less to wait for instructions
  • You use AI daily — Claude, ChatGPT, or similar — to draft, research, and plan, and you've built at least one automation or workflow that removed a recurring task from someone's plate. Claude Code experience is a real advantage
This isn't for you if
  • You've supported a team or a department but never a single principal whose life you actually ran
  • You present options because deciding feels risky
  • You need the week defined for you — this role defines someone else's week
  • You're uncomfortable managing another person (you'll direct the House Manager)
  • You've never set up an AI tool or automation on your own and don't want to learn
Hard requirement: 2+ years running the life of a single principal. We're hiring from the US, South Africa, and Europe/Latin America at the same time, and we'll hire the best candidate regardless of where they live.

Section 06

Compensation & Structure

Set by experience and market. Reviewed at 90 days.

1
Compensation

Set by Ravi based on your experience and your market, and shared with you on the first call. Contractor structure; paid once a month at month-end. The number reflects what you've actually run before — it isn't negotiated after the offer.

2
Remote

You work from wherever you are, with at least 5 hours of overlap with 8 AM–5 PM US Central, Monday–Friday. Occasional travel with Ravi — Miami, Europe, team offsites, expenses covered — is a plus if you're able and willing. It is not a requirement.

3
Your First 30 Days

Week 1: full access, meet the House Manager, inherit their list, clean the board — mark what's done, kill what's dead, put an owner and a date on the twelve projects that have been open since July. Weeks 2–4: drive three transactions currently stuck in progress (a sale, a refinance, a payoff) to close, working with the broker, the lender, and the family office — together they're worth far more than this role costs. Alongside: the first fully pre-built Saturday, the go-bag done, the travel SOP written. Day 30: Ravi has spent 30 minutes a week on his personal life. Everything else happened.

4
The Hiring Process — Same-Day Decisions at Every Step

Apply below (hard filters up front so we don't waste your time) → 20-minute video screen with Ravi → 30-minute finaltwo-week paid trial at full hours → offer.

Section 07

Apply Now

About five minutes plus a short Loom. The first three questions are hard filters — answer them honestly so neither of us wastes a week. Then one written answer and the Loom. We watch every Loom; that's where the signal is. Everything else we'll cover on a 20-minute call.

Record a 2–3 minute Loom answering these two questions, in order:
  1. Your last principal: who they were (role and type of business or family — no names), how long you supported them, and three things you owned end-to-end without being asked.
  2. Scenario: It's Thursday at 4 PM. Ravi texts you: "Miami tomorrow through Sunday." Walk me through the next three hours — what you book, in what order, what you tell him, and what you tell the House Manager.
Be specific. Real examples beat general claims every time.