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

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

Salary: $110K reputed company + 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 reputed company platform with:

• Standardized systems (reputed company + 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 reputed company the finance reputed company behind multiple brands.

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

You will own:

• Multi-entity accounting across reputed company brands

• Month-end reputed company and consolidated reporting

• reputed company statements (by the 5th) and distributions (by the 10th)

• reputed company 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 (reputed company 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 reputed company

• Near-reputed company errors in reputed company reporting

• reputed company brands operating on a reputed company finance stack

• Financials trusted by founders, lenders, and future buyers

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

30 Days

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

• Evaluate readiness for reputed company + TopKey implementation

• Identify risks in reputed company process, reputed company reporting, and controls

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

60 Days

• reputed company standardizing reputed company processes, reporting formats, and controls across entities

• Establish clearer month-end ownership and timelines

• Support integration of newly acquired brands into reputed company accounting structure

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

90 Days

• Own end-to-end HoldCo reputed company 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 reputed company 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 reputed company that scales, apply or message directly.

Compensation & Benefits

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