Director of Operations & Customer Success
Remote, Latin America · Full time · US Eastern hours · $2,000 to $3,000 USD/month plus performance bonus
The company
The Vesta Group owns hotels and builds the software that runs them.
We acquire underperforming real estate in top destination markets, reposition it into experiential boutique hospitality that commands premium rates, and then operate it better than anyone else in the market. Today that is a first of its kind wellness resort in the Ozarks, 50 rooms, a portfolio of short term rental properties in Florida, and an active pipeline for the next acquisition. We are scaling aggressively and we are not slowing down.
This is not a first attempt at any of it:
- Founded 2021. Roughly $16M across nine properties and seven successful exits, at an average return on equity above 200 percent.
- Our South Florida luxury rental portfolio was acquired by a private equity fund backed by the former Chairman of Hilton, and we then joint ventured with that fund to acquire over $10M in hospitality assets.
- We take tired assets and reprice them. Our current resort was a roadside motel renting at about $70 a night. It now runs at more than double that, on the same road.
- Our founder built and exited a seven figure e commerce brand, wrote a number one Amazon new release on short term rentals, and has been featured in Forbes.
- Everything is in house. Brand, design, websites, marketing, revenue management, automation. No agencies. Our paid campaigns run at roughly 20x return on ad spend.
And now the software
YieldWizard.AI is an AI operating system for hotels.
Every independent hotel owner is flying blind. Their numbers sit across a booking system, a channel manager and an accounting file that never agree, and nobody tells them where the money is actually going. YieldWizard connects all of it and answers what matters: where is revenue leaking, which rooms are underpriced, and what do you do about it this week. Tens of thousands of hotels have this problem and almost nothing is built for them. Most hotel software is built by people who have never run a hotel. Ours is tested on our own properties before a customer ever sees it.
That is the thesis: vertically integrate hospitality. Own the real estate, build the technology that runs it better than anyone else can, then sell that technology to every other hotel owner in the market. We are looking for one exceptional person to join us for the ride.
Why this role exists
This role was designed for two primary purposes:
1. To own daily operations, project execution and team accountability across the hospitality business, so the founder can spend his time on growth, acquisitions and capital instead of chasing whether something got finished.
2. To own customer onboarding, retention and partnerships for YieldWizard, so the founder can spend his time building the product and selling it instead of running every onboarding call himself.
Both are the same underlying job: you free up the owner's time on both fronts, and you do it by building systems rather than by absorbing chaos. In return you get a rare education in what it actually takes to build a hospitality and technology company from the ground up.
Summary of responsibilities
1. YieldWizard customer success (the largest part of the role)
- You will be on calls all day, dozens a week. Onboarding hotel owners, connecting their systems, getting them to the moment the product tells them something about their business they did not know.
- You own retention: spotting accounts going quiet before they churn, and doing something about it.
- You turn every problem into a better process, so each customer onboards faster than the last.
- Crucial here: warmth on a call, explaining technical things to non technical people, and the discipline to follow up until someone actually completes a step.
2. Partnerships and project management
- You drive our integration partnerships with hotel technology companies from signed agreement to live integration, coordinating both sides through paperwork, technical access and launch.
- You run projects across the hospitality business the same way, coordinating vendors and internal owners so each phase completes and hands off cleanly.
- You are the one who spots a conflict early rather than reporting it late.
- Crucial here: seeing problems and their downstream impact early, and holding external parties to what they committed to.
3. The channel between the team and ownership
- You are the gatekeeper. Only the genuinely important things reach the founder. Anything that can be handled at your level gets handled there, without being asked twice.
- You run it downward too, passing decisions and context to the team so people understand not just what to do but why.
- You hold the communication rhythm: weekly reporting, a published scorecard, and clear escalation when something is off track.
- Crucial here: high interpersonal skill, and being willing to crack the whip when needed while still being someone people want to work with.
4. Proactively finding what needs fixing
- You have eyes everywhere, spot what is not working, and arrive with a proposed solution rather than a report of the problem.
- You build standard operating procedures where none exist: guest experience, performance benchmarking, process design, hiring practices.
- You develop a working understanding of the numbers and use them to decide where attention goes.
- Crucial here: self starting, and knowing precisely when to involve the founder and when not to.
Your first 90 days
- You run customer onboarding end to end, with the founder off the calls.
- Every customer signed since you started is live and using the product, or you can say precisely why not.
- Three integration partnerships closed and live.
- A documented onboarding process exists, written by you from the calls you ran.
- You flag at risk accounts before anyone asks.
- Every recurring task in the company has an owner and a date, and late tasks are near zero.
Who you work with
You work directly with the owner. Not with a manager who reports to a director. You bring him a decision, you get an answer the same day, and you own what happens next.
You will have direct reports, starting with our executive assistant and growing as we do. You coordinate daily with our General Manager, who runs the resort and its fifteen person team, and you manage our vendors and partners.
Desired skills and background
- Honesty and integrity come first, with no flexibility. You will have visibility into money, systems and people.
- Perfect English, spoken and written. The one requirement we will not bend on. You are on video with American hotel owners every day and writing to them in between, so it needs to be effortless to listen to and clean on the page.
- Real ability with people on calls. Warm, clear, and able to move a friendly conversation toward a decision.
- 3 to 6 years in customer success, onboarding, account management, client delivery, hospitality or project management operations.
- A specific story about chasing someone who did not report to you until they delivered. We will ask what you did on day three.
- Genuine fluency with AI tools, used daily in real work. Not curiosity, not a course you took.
- Systems oriented and low ego. You enjoy the details, you build structure and maintain it, and you do not sit idle waiting for an assignment.
- Bonus if you have administered a task system like ClickUp or Asana rather than just working inside one.
Nice to have: onboarding customers onto software, a hospitality or real estate background, SOPs you have written yourself, HR or hiring experience.
How you will be measured
Goal setting with the owner in week one. Weekly check ins and a published scorecard everyone can see. Quarterly performance reviews and an annual compensation review.
How we work
Accountability. You do what you said, by when you said it. Everyone is on the same scorecard, including the owner. You will be held to your dates, and you will get a decision from him the same day when you are blocked on him. Accountability that only runs downward is just pressure. Ours runs both ways.
Kaizen. Solve a problem once, then write the process that stops it recurring, the same day. The scoreboard is how many problems repeat, and that number goes down every quarter.
AI first. We run a resort, a rental portfolio and a software company on a very small team because we automate relentlessly. Our asset management is roughly 90 percent automated. Everyone here is expected to be genuinely fluent with AI tools and to keep getting better at them.
Not for you if
- You do not enjoy being on calls. You will live on them.
- Your English is good but effortful, or your writing needs editing.
- You want strategy work. This is execution, and the details are the job.
- You are uncomfortable telling a customer, a colleague or a vendor that something is late.
- You are not already using AI in your daily work.
How to apply
Apply here: https://forms.clickup.com/9016321605/f/8cpm9j5-15436/W9UTOC058JWPQMMS92
- Ten minutes. You will need your CV and a 60 second video of yourself speaking English, recorded on your phone. No editing, no script. We watch it first. We do not accept applications by email.