Sales Manager, Homeowner Partnerships (Springfield)

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.

The Role

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.

What You’ll Do

• 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 improve Red Cottage’s sales process, positioning, and market strategy.
• Represent Red Cottage in market when needed, including property visits, local meetings, networking, events, and partner development.
• Help strengthen and professionalize Red Cottage’s homeowner acquisition engine as we scale.

What We’re Looking For

• 4+ years of experience in sales, business development, partnerships, account management, real estate, hospitality, vacation rentals, proptech, luxury services, or another adjacent field.
• Direct experience in the vacation rental, short-term rental, second-home, property management, or hospitality industry is strongly preferred.
• A proven ability to manage and close consultative, high-value sales.
• Strong understanding of how to build trust with homeowners, real estate partners, and other sophisticated stakeholders.
• Excellent written and verbal communication skills.
• A polished, warm, and credible presence with affluent homeowners.
• Strong commercial judgment and the ability to determine which opportunities are worth pursuing.
• Comfort managing both inbound opportunities and self-sourced business development.
• Strong organization, follow-through, and pipeline discipline.
• Ability to work independently across multiple markets without daily hand-holding.
• Familiarity with Northeast leisure markets, second-home communities, or regional real estate dynamics.
• A consultative sales style rather than a transactional one.
• Comfort with CRM systems, sales reporting, and performance accountability.
• Northeast-based, with the ability and willingness to travel regularly across Red Cottage markets.
• Driver’s license required.

You’ll Be Successful If You

• Consistently convert qualified homeowner opportunities into signed management agreements.
• Build a healthy pipeline through inbound follow-up, outbound sourcing, referrals, and local market relationships.
• Make homeowners feel informed, respected, and confident in choosing Red Cottage.
• Balance warmth and relationship-building with clear commercial judgment.
• Understand which homes belong in the Red Cottage portfolio and which do not.
• Move opportunities forward with urgency, persistence, and professionalism.
• Maintain a clean, accurate, and actionable pipeline.
• Build credibility with internal teams by handing off signed owners with clear context and expectations.
• Help Red Cottage better understand market dynamics, homeowner objections, and competitive positioning.
• Contribute to a repeatable homeowner acquisition process as the company scales.

Why Red Cottage

• Join a growing hospitality company with a differentiated brand and significant expansion opportunity.
• Help shape the next phase of growth for one of the leading design-driven vacation rental platforms in the Northeast.
• Work with distinctive homes, discerning homeowners, and some of the region’s most desirable leisure markets.
• Take ownership of meaningful revenue-generating opportunities rather than sitting in a narrow sales seat.
• Partner directly with company leadership, revenue management, onboarding, operations, and local market teams.
• Earn performance-based compensation tied to your ability to source, manage, and close high-quality opportunities.

Compensation

Competitive base salary plus performance-based incentive compensation.

Red Cottage is an equal opportunity employer. We value different backgrounds, perspectives, and experiences and encourage candidates who are excited about the opportunity to apply, even if they do not meet every qualification.