[Hiring] Chief of Staff @Stayd Collective

Role Description

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.
• 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:

• Map how something works today.
• Find 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.

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.

Qualifications

• Excellent written English and grammar.
• Strong operations and invoicing experience, ideally across multiple platforms and many client accounts.
• An AI-first, proactive mindset.
• A track record of designing and improving processes.
• Comfort juggling many channels, tools, and time zones.
• Experience in cleaning, hospitality, or property management is a strong plus.
• Reliable internet and a quiet place to work.

Requirements

• 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.
• 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.

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.

Company Description

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.