Chief of Staff

Chief of Staff

Haven
Full-time | Remote 

Department: Corporate

Schedule: Monday–Friday | Shift starts at 8am ET

Reports to: COO, Cleaning

Compensation: USD $1,500–$1,700 / month

About the brand

Haven manages cabins and mountain homes in the Great Smoky Mountains and around Knoxville, Tennessee. Steep driveways, hot tubs, wood stoves, and a season that swings from quiet weeks to a full house every weekend. It is a market where property care is guest experience: a cold hot tub is a ruined anniversary, and a turnover that runs late is a family waiting in the driveway.

The role

You are the COO's right hand for the cleaning business. You run the day-to-day so leadership can focus on strategy: invoices go out correct and on time, cleaners and clients get clear answers, and nothing falls between the dozen tools we use to run the operation. Your morning starts with the COO's priorities, overnight messages and anything urgent from a client or cleaner. By the end of the day, the COO knows what got done, what is pending and what needs a decision tomorrow.

It is a role for someone who wants to design better processes, not just execute existing ones. You will map how something works today, find the steps that can be simplified or automated with AI, test a better way and write it down so it sticks. Doing a task every week is not the same as fixing it. If a workflow is yours, you own making it better.

Where you sit

You sit in Corporate and work directly with the COO of the cleaning business, with daily contact with cleaners, field operations, clients and the admin team. This is not a role where you are handed a queue and left alone.

Because Stayd runs shared systems across every brand, a process you improve here tends to end up running in six other markets, which is the closest thing we have to a promotion path.

What you'll own

• The day-to-day of the cleaning business, run alongside the COO across clients, properties and cleaning teams.
• Invoicing for many clients across multiple platforms: creating, checking, sending, following up and reconciling discrepancies.
• Communication with clients, cleaners and internal teams across email, SMS, WhatsApp, Slack and our PMS/CRM, in clear, professional English.
• Deep knowledge of how the business runs: pricing, scheduling, quality standards and SOPs.
• Processes designed, documented and improved, with bottlenecks spotted and solved before anyone asks.
• AI tools used to automate repetitive work, draft messages, summarize information and expand what one person can get done.
• Key metrics like invoicing timeliness, response times and cleaning completion rates, tracked and reported to the COO.
• Special projects from the COO, such as new cleaning packages, large client onboardings and new tools or workflows.

How you'll live our core values

Five values run this company, and we hire and promote against them.

• See Something Do Something: if you spot it, it is yours. Nobody here is allowed to walk past a problem because it belongs to another team.
• Do What You Say: a commitment with a date on it is a promise. If it slips, you say so before it is late, not after.
• Own the Miss: we get things wrong. What matters is that you name it first, fix it, and make sure it cannot happen the same way twice. Nobody is punished for a miss they owned.
• Say the Hard Thing: kindly, directly and early. Silence in a meeting followed by a private complaint is the one behaviour we will not carry.
• Make It Better: leave the process, the property or the shift in better shape than you found it. Small improvements, constantly, beat big ones occasionally.

What you bring

• Excellent written English and grammar. Every message you send to a client or cleaner reflects the company.
• Strong operations and invoicing experience, ideally across multiple platforms and many client accounts.
• An AI-first, proactive mindset: your first question about a repetitive task is how to stop doing it by hand.
• A track record of designing and improving processes, not only following them.
• Comfort juggling many channels, tools and time zones without losing track of what is open.
• Experience in cleaning, hospitality or property management is a strong plus.
• Reliable internet and a quiet place to work.

Compensation & Benefits

• $1,500–$1,700/month, depending on experience.
• Fully remote, with flexible scheduling within U.S. time-zone overlap.
• A path to grow into a broader operations leadership role across the portfolio.