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 HoldingsStayd 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 financialsOperational excellence across every brandWe are building industry-leading accounting infrastructure to drive financial clarity, trust, and scalable growth across every property and market we serve..The RoleWe 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 brandsMonth-end close and consolidated reportingOwner statements (by the 5th) and distributions (by the 10th)NetSuite and TopKey implementationBuilding and leading a lean accounting team (onshore and nearshore)What You Bring7+ years of accounting experience, including Controller or equivalent senior finance leadership roleExperience with multi-entity or holding company structuresStrong GAAP and consolidation knowledgeERP implementation experience (NetSuite preferred)Systems-oriented with a willingness to be hands-on earlyExperience with M&A accounting, including acquisitions, integrations, and purchase accountingBonus: experience in short-term rentals, property management, real estate, or hospitalityWhat Success Looks LikeClean, fast, and reliable monthly closeNear-zero errors in owner reportingAll brands operating on a unified finance stackFinancials trusted by founders, lenders, and future buyersWhat Success Looks Like (30 / 60 / 90 Days)30 DaysAssess current entity structures, accounting workflows, and reporting gaps across brandsEvaluate readiness for NetSuite + TopKey implementationIdentify risks in close process, owner reporting, and controlsReview any active or recent acquisitions and understand current M&A accounting treatment60 DaysBegin standardizing close processes, reporting formats, and controls across entitiesEstablish clearer month-end ownership and timelinesSupport integration of newly acquired brands into unified accounting structureImplement consistent M&A accounting practices, including purchase accounting and opening balance alignment90 DaysOwn end-to-end HoldCo close and consolidated reportingEnsure newly acquired entities are fully integrated into systems, reporting, and controlsEstablish repeatable M&A integration playbooks for future acquisitionsImprove reliability and accuracy of owner reporting and financial statementsWhy This RoleBuild a finance function from scratch, the right wayWork directly with high-performing, fast-moving foundersBe a key contributor to a future private equity recap or exitHigh ownership, high impact, minimal bureaucracyCall to ActionIf 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)