Business Development Associate

Hybrid Business Development Associate role on Cape Cod, emphasizing multi-touch outreach to high-value homeowner prospects, qualifying opportunities, and supporting an AI-enhanced sales process with potential growth into direct sales.

Responsibilities

• Execute multi-touch outreach to high-value Cape Cod homeowner prospects.
• Leverage AI tools for prospect research, personalized outreach, timely follow-ups, and proposal preparation.
• Respond promptly to interested prospects and initiate calls when a conversation will advance the opportunity.
• Qualify homeowners based on interest, fit, decision-making authority, and assess property quality, availability, and revenue potential.
• Prepare preliminary rental-income projections using the established model and market comps.
• Book qualified, well-prepared owner conversations with the executive team.
• Maintain an accurate, current CRM and keep the sales pipeline moving.
• Reconnect with past prospects and nurture local referral relationships.
• Visit homes and meet with homeowners to assess property, understand goals, and determine next steps.
• Assist in improving and automating the sales process as you identify effective approaches.

Requirements

• Results-oriented executor who thrives with a clear system, targets, and measurable outcomes.
• Motivated by earnings growth tied to your results.
• Comfortable using AI tools such as ChatGPT and Claude, or eager to become proficient quickly for research, drafting, and workflow improvements.
• Organized, self-directed, and capable of moving the pipeline with minimal supervision.
• Resilient and consistent, able to handle rejection and continue forward with outbound outreach.
• Credible, trustworthy communicator who can speak confidently with homeowners by phone and in person.
• Strong, natural writer who can tailor templates or AI drafts into personal, specific messages.
• Comfortable with numbers and able to build clean income projections in a spreadsheet or pro forma tool.
• Experience in real estate, vacation rentals, hospitality, or property management is a plus.

Technologies

• ChatGPT
• Claude
• CRM
• Spreadsheet

Benefits

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

Compensation

USD 55,000 - 70,000 per year

Location

• Hybrid role based in Brewster, MA; approximately two days per week on Cape Cod, with flexibility based on business needs. Local or South Shore candidates who can travel to the Cape regularly are encouraged to apply.
• Reliable transportation is required.
• Some weekend availability is required; schedule will flex to meet homeowner needs.

Application questions

• 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 located within a realistic commuting distance and able to meet this requirement?
• What town and state would you commute from?