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

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)