Sales Jobs in Brewster, MA

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1mo ago

Business Development Associate

Nauset Rental Brewster, MA

Brewster, MA

1mo ago Closed

$55k - $70k/yr Full time Ai Assisted Prospecting Business Development Client Prospecting

This position is no longer accepting applications (closed Aug 23, 2026).

Job Description

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?

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