Sales Manager, Homeowner Partnerships

Red Cottage is a design-driven hospitality and vacation rental management company representing exceptional homes throughout the Northeast.

We help homeowners unlock the full potential of their properties through professional management, thoughtful hospitality, strong direct-booking demand, revenue strategy, and a brand guests trust. Our portfolio spans some of the Northeast’s most desirable leisure markets, including the Hudson Valley, Catskills, Berkshires, Connecticut, the Hamptons, North Fork, Vermont, Maine, and beyond.

As we continue to grow, we are looking for an experienced sales and business development professional to help us bring the right homeowners and homes onto the Red Cottage platform.

About Red Cottage

Red Cottage is a design-driven hospitality and vacation rental management company representing exceptional homes throughout the Northeast.

We help homeowners unlock the full potential of their properties through professional management, thoughtful hospitality, strong direct-booking demand, revenue strategy, and a brand guests trust. Our portfolio spans some of the Northeast’s most desirable leisure markets, including the Hudson Valley, Catskills, Berkshires, Connecticut, the Hamptons, North Fork, Vermont, Maine, and beyond.

As we continue to grow, we are looking for an experienced sales and business development professional to help us bring the right homeowners and homes onto the Red Cottage platform.

We are looking for a Sales Manager to own and close homeowner acquisition opportunities across Red Cottage’s Northeast markets.

This is not an entry-level sales role. We are looking for someone with meaningful experience in vacation rentals, property management, hospitality, real estate, proptech, luxury services, or another adjacent relationship-driven industry. The right person understands how to build trust with homeowners, qualify high-value opportunities, manage a disciplined pipeline, and close consultative sales with professionalism and credibility.

You will work across inbound and outbound channels, including homeowner inquiries, referrals, real estate relationships, local market sourcing, and targeted business development. You will be responsible for moving qualified opportunities from first conversation through signed management agreement, while ensuring that every prospective owner has a polished, thoughtful, and distinctly Red Cottage experience.

Success in this role requires industry fluency, commercial judgment, strong follow-up, and the ability to speak confidently with discerning homeowners who are making an important decision about a valuable property.

• Own homeowner sales opportunities from initial conversation through signed management agreement.
• Respond promptly and professionally to inbound homeowner inquiries across phone, email, web forms, referrals, and partner channels.
• Develop outbound and relationship-driven opportunities in priority Northeast markets.
• Conduct discovery calls to understand each homeowner’s property, goals, ownership history, rental expectations, current management situation, and decision-making process.
• Clearly communicate Red Cottage’s services, operating model, revenue approach, hospitality standards, and owner value proposition.
• Qualify prospective homes based on location, design, condition, revenue potential, operational complexity, homeowner expectations, and overall portfolio fit.
• Build trust with homeowners, real estate agents, local partners, and referral sources.
• Manage objections around revenue, fees, exclusivity, service levels, platform alternatives, and prior property management experiences.
• Coordinate property evaluations, revenue reviews, and internal underwriting with operations, onboarding, revenue management, and local market teams.
• Prepare thoughtful owner follow-up, proposals, and next steps that move opportunities forward.
• Maintain a disciplined and accurate CRM, including lead status, activity, notes, deal stage, next steps, and forecasted close timing.
• Track pipeline, conversion rates, deal velocity, source performance, and market-level learnings.
• Share competitive intelligence and homeowner feedback to…