Business Development Associate

Nauset Rental — Brewster, Cape Cod
Full-time

Hybrid role serving Cape Cod. Remote work with approximately two planned days per week on Cape Cod. Candidates based in Plymouth, Kingston, Carver, Wareham, the Upper Cape, or surrounding areas are encouraged to apply.

Nauset Rental is building the leading vacation rental management company for high-end homes on Cape Cod, with a goal of 40% year-over-year growth.

We’re looking for a driven, tech-forward business development professional to help turn premium homeowner prospects into new business.

We already have the foundation: a strong database, defined outreach playbook, proven templates, AI tools, revenue-projection models, and a compelling homeowner offering. Your first job is to run that system consistently, keep prospects moving, and create qualified opportunities for our leadership team.

As you demonstrate strong judgment, sales ability, and follow-through, the role will expand. You’ll help improve and automate our AI-supported sales process while taking on more direct homeowner conversations, proposal strategy, negotiation, closing, and client relationship ownership.

What you’ll do

• Run multi-touch outreach to high-value Cape Cod homeowner prospects.
• Use AI tools for prospect research, personalized outreach, follow-up, and proposal preparation.
• Respond quickly to interested prospects and call when a conversation will move the opportunity forward.
• Qualify homeowners based on interest, fit, decision-making authority, and the home’s quality, availability, and revenue potential.
• Prepare preliminary rental-income projections using our established model and market comps.
• Book qualified, well-prepared owner conversations with the executive team.
• Keep the CRM and pipeline accurate, current, and moving.
• Reconnect with past prospects and nurture local referral relationships.
• Visit homes and meet with homeowners to assess the property, understand their goals, and determine next steps.
• Help improve and automate the sales process as you learn what works.

We are a small, growing company with a close-knit team. During peak season, you may occasionally step in to support urgent guest communications, property needs, or limited on-call coverage. A team-first attitude and willingness to help when needed are important.

Who you are

• An executor who likes a clear system, target, and measurable results.
• Motivated by earning more when your work produces more.
• Comfortable using AI tools such as ChatGPT and Claude—or highly motivated to become proficient quickly—for research, drafting, and workflow improvement.
• Organized and self-directed, and you keep your pipeline moving without constant oversight.
• Resilient and consistent. Outbound work means hearing “no” and continuing forward.
• A credible, trustworthy communicator who can speak confidently with homeowners by phone and in person.
• A strong, natural writer who can turn a template or AI draft into a message that feels personal and specific.
• Comfortable with numbers and can build a clean income projection in a spreadsheet or pro forma tool.
• Experience in real estate, vacation rentals, hospitality, or property management is a plus.

Relevant backgrounds may include inside sales, business development, recruiting, real estate, account management, hospitality, leasing, or property management.

Location

This is a hybrid role, not a fully remote position.

We expect approximately two days per week in Brewster or elsewhere on Cape Cod, based on business needs. We are open to someone based locally or on the South Shore who can travel to the Cape consistently.

Reliable transportation is required. Some weekend availability is required - prospective homeowners often want to meet while they are at their Cape homes. The schedule will flex accordingly.

Compensation and growth

This role includes a competitive base plus bonus. Base compensation is expected to fall between $45,000 and $55,000, depending on experience, plus meaningful bonus structure tied to performance, qualified opportunities and signed homes.

Expected total compensation for a strong first-year performer is approximately $60,000–$70,000+, with additional upside based on delivery and as the role expands into direct sales and closing.

As you take on more responsibility for direct sales, negotiation, closing, and owner relationships, your compensation structure and earning potential will grow accordingly.

This is ideal for someone who wants to work hard, prove what they can do, and build a much larger, higher-earning role within a scaling company.

How to apply

Send your resume and a short note to describing a time you helped create or move new business forward.

Bonus points if you explain how you would use AI to reach a large prospect list while keeping the outreach thoughtful, accurate, and human.

Pay: $55,000.00 - $70,000.00 per year

Benefits:

• 401(k) matching
• Paid time off
• Work from home

Application Question(s):

• Do you have reliable transportation and a valid driver’s license?
• This role requires approximately two days per week on Cape Cod, primarily in Brewster, plus occasional homeowner meetings elsewhere on the Cape. Are you currently located within a realistic commuting distance and able to meet this requirement?
• What town and state would you commute from?

Work Location: Hybrid remote in Plymouth, MA 02360