Controller – Multi-Brand Vacation Rental Platform (Remote, US-Based)

Salary: $110K base + performance bonus (OTE ~$150K)

About Stayd Holdings

Stayd is a fast-scaling, multi-brand vacation rental platform managing thousands of properties across multiple markets.

We are building a unified platform with:

• Standardized systems (NetSuite + TopKey)

• Institutional-grade financials

• Operational excellence across every brand

We are building industry-leading accounting infrastructure to drive financial clarity, trust, and scalable growth across every property and market we serve..

The Role

We are hiring our first HoldCo Controller to build and lead the finance engine behind multiple brands.

This is a build-and-scale mandate, not a steady-state accounting role.

You will own:

• Multi-entity accounting across all brands

• Month-end close and consolidated reporting

• Owner statements (by the 5th) and distributions (by the 10th)

• NetSuite and TopKey implementation

• Building and leading a lean accounting team (onshore and nearshore)

What You Bring

• 7+ years of accounting experience, including Controller or equivalent senior finance leadership role

• Experience with multi-entity or holding company structures

• Strong GAAP and consolidation knowledge

• ERP implementation experience (NetSuite preferred)

• Systems-oriented with a willingness to be hands-on early

• Experience with M&A accounting, including acquisitions, integrations, and purchase accounting

• Bonus: experience in short-term rentals, property management, real estate, or hospitality

What Success Looks Like

• Clean, fast, and reliable monthly close

• Near-zero errors in owner reporting

• All brands operating on a unified finance stack

• Financials trusted by founders, lenders, and future buyers

What Success Looks Like (30 / 60 / 90 Days)

30 Days

• Assess current entity structures, accounting workflows, and reporting gaps across brands

• Evaluate readiness for NetSuite + TopKey implementation

• Identify risks in close process, owner reporting, and controls

• Review any active or recent acquisitions and understand current M&A accounting treatment

60 Days

• Begin standardizing close processes, reporting formats, and controls across entities

• Establish clearer month-end ownership and timelines

• Support integration of newly acquired brands into unified accounting structure

• Implement consistent M&A accounting practices, including purchase accounting and opening balance alignment

90 Days

• Own end-to-end HoldCo close and consolidated reporting

• Ensure newly acquired entities are fully integrated into systems, reporting, and controls

• Establish repeatable M&A integration playbooks for future acquisitions

• Improve reliability and accuracy of owner reporting and financial statements

Why This Role

• Build a finance function from scratch, the right way

• Work directly with high-performing, fast-moving founders

• Be a key contributor to a future private equity recap or exit

• High ownership, high impact, minimal bureaucracy

Call to Action

If you have built or want to build a multi-entity accounting engine that scales, apply or message directly.

Compensation & Benefits: 

Salary: $110K base + performance bonus (OTE ~$150K)