Outbound Business Development Representative

Outbound Business Development Representative About Red Cottage Red Cottage is a design-driven vacation rental management and hospitality platform serving the Northeast’s most sought-after leisure markets, including the Hudson Valley, Catskills, Berkshires, Connecticut, the Hamptons, North Fork, Vermont, Maine, and beyond. We manage distinctive homes for discerning owners and deliver highly curated stays for guests who care about design, service, and experience. Our platform combines strong direct booking demand, premium hospitality standards, local market expertise, and a trusted brand that homeowners are proud to be associated with. As we continue to grow, we are looking for a driven, polished, and highly proactive business development professional to help us identify, engage, and sign the right homes for the Red Cottage portfolio. The Role This is a proactive outbound business development role focused on homeowner acquisition. You will be responsible for identifying high-potential homes and owners across our target markets, initiating conversations, building trust, and converting qualified prospects into signed management agreements. This is not a passive inbound sales role. You will be expected to generate your own pipeline through outbound calling, email, text, local sourcing, referrals, market research, and in-person relationship building. You will often be the first meaningful interaction a homeowner has with Red Cottage. That means you need to be commercially sharp, highly credible, warm, persistent, and able to speak to sophisticated homeowners who care deeply about their properties. The right person will be comfortable picking up the phone, walking into a market, building local relationships, and clearly articulating why Red Cottage is a better home for a premium vacation rental than the alternatives. What You’ll Do Proactively source and contact prospective homeowners across Red Cottage’s current and target markets. Run a high volume of outbound calls, with thoughtful follow-up by email, text, and other appropriate channels. Build and manage a disciplined pipeline of owner prospects from lists, referrals, local research, existing relationships, and market intelligence. Own the sales cycle from first contact through discovery, qualification, pitch, objection handling, follow-up, and signed management agreement. Learn each market deeply enough to understand local property types, owner motivations, rental dynamics, competitive managers, and Red Cottage’s positioning. Represent Red Cottage in person when needed, including market visits, homeowner meetings, local networking, events, and property walk-throughs. Communicate the Red Cottage value proposition clearly, including our direct booking strength, hospitality standards, design sensibility, owner care, guest experience, and operating platform. Qualify homes thoughtfully, ensuring that prospects are a fit for the Red Cottage brand, guest expectations, revenue potential, and operational standards. Coordinate smoothly with the onboarding and operations teams once an owner is signed. Maintain clean, current, and detailed CRM records, including prospect status, notes, next steps, and market feedback. Share insights from the field, including owner objections, competitive intelligence, market opportunities, and emerging acquisition channels. Help Red Cottage build repeatable outbound systems for homeowner acquisition across multiple Northeast markets. Who You Are You have 2+ years of experience in outbound sales, business development, real estate, hospitality, luxury services, home services, or another relationship-driven sales environment. You are genuinely comfortable with cold outreach and do not need warm leads handed to you. You are energized by the hunt: finding the right prospects, starting conversations, following up, and creating opportunities where none existed before. You can be persistent without being pushy, and polished without sounding scripted. You know how to build trust with discerning, affluent, and often skeptical homeowners. You are commercially minded and can connect Red Cottage’s brand, service model, and economics to what matters most to an owner. You are highly organized and capable of managing your own pipeline without daily hand-holding. You have strong written and verbal communication skills and can represent a premium brand with warmth, clarity, and credibility. You are comfortable working independently, spending time in-market, and moving between phone-based outreach and in-person relationship building. You have good judgment around which homes and owners are worth pursuing. You are curious, resourceful, and willing to learn the vacation rental, hospitality, and second‑home ownership landscape in depth. Familiarity with the Northeast, the Hamptons, North Fork, Hudson Valley, Catskills, Berkshires, Vermont, Maine, real estate, or vacation rentals is a strong plus. A driver’s license and willingness to travel within Red Cottage markets are required. What Success Looks Like You are consistently building and advancing a pipeline of qualified homeowner prospects. You are creating new opportunities through outbound activity, referrals, and local market presence. You are signing homes that fit Red Cottage’s standards and growth strategy. Homeowners see you as credible, knowledgeable, and trustworthy. Internal teams receive clean handoffs and clear context on newly signed owners. Red Cottage gains sharper visibility into target markets, competitive dynamics, and future growth opportunities because of your work. Why This Role Matters Red Cottage’s growth depends on bringing the right homes and homeowners onto the platform. This role sits at the front edge of that growth. You will help shape the future of our portfolio, expand our presence in key Northeast markets, and introduce homeowners to a more thoughtful, hospitality-driven way to manage and monetize their properties. #J-18808-Ljbffr Red Cottage Inc.