Director of Hospitality Real Estate & Asset Strategy

Position OverviewThe Director of Hospitality Real Estate & Asset Strategy will be responsible for identifying, evaluating, and structuring partnerships with developers, property owners, and institutional investors seeking hospitality-focused operating solutions for multi-unit assets.Working closely with company leadership, this individual will support the expansion of Red Cottage’s platform into larger hospitality assets, ensuring that the company’s operating model can be effectively applied to buildings and developments that combine residential design with hotel-style guest use.The role requires strong experience in real estate underwriting, hospitality operations, and asset-level financial performance, as well as the ability to work with development teams and ownership groups in structuring long-term operating partnerships.Key ResponsibilitiesReal Estate Opportunity SourcingDevelop relationships with multifamily developers, hotel owners, and real estate investors across the NortheastIdentify development and acquisition opportunities where Red Cottage’s operating platform could support short-term rental or hybrid hospitality modelsMaintain awareness of development pipelines, zoning frameworks, and emerging hospitality markets in the regionFinancial Analysis & UnderwritingEvaluate prospective assets and developments through detailed financial modeling, including projections for:Average daily rate (ADR)occupancyrevenue per available unitoperating expenses and marginsAssess the viability of short-term rental hospitality models within multifamily or boutique hotel contextsProvide investment and operational analysis to internal leadership and potential partnersOperating Partnership StructuringWork with developers and ownership groups to structure operating and management agreements for multi-unit hospitality assetsTranslate Red Cottage’s operational model into asset-level performance assumptionsSupport negotiations related to management contracts, revenue-sharing structures, and operating frameworksPlatform IntegrationCollaborate internally to ensure Red Cottage’s technology, distribution, and operations platform can be effectively applied to larger assetsHelp define operational strategies for multi-unit properties, including guest services, distribution channels, and revenue management approachesMarket Strategy & ExpansionContribute to Red Cottage’s broader strategy for expansion into hospitality real estate partnershipsMonitor market trends across the hotel, short-term rental, and residential hospitality sectorsProvide insight into how Red Cottage’s operating model can evolve to support institutional or development-scale assetsQualifications7–12 years of experience in real estate finance, hospitality asset management, development, or related fieldsDemonstrated experience underwriting hospitality, hotel, or multifamily real estateStrong financial modeling and analytical skillsFamiliarity with hotel or short-term rental operating economicsExperience working with developers, ownership groups, or institutional investorsStrong communication and relationship management skillsPreferred BackgroundsCandidates may come from backgrounds such as:Hospitality asset managementReal estate private equityHotel development or acquisitionsMultifamily development with hospitality componentsHospitality operating platforms or branded residence projectsAbout Red CottageRed Cottage is a premier hospitality platform focused on the management and marketing of design-driven vacation homes across the Northeast, including the Hudson Valley, Catskills, Berkshires, and Hamptons. Through a combination of technology, operations, and curated hospitality programming, Red Cottage has developed a differentiated operating model for distinctive properties in destination markets.