Sales Representative Homeowner Acquisition

Company Overview

Juniper Holiday + Home specializes in managing vacation rental properties throughout Southwest Michigan. We are known for delivering exceptional guest experiences while helping homeowners maximize the value and performance of their investment properties.

At Juniper, we combine local market expertise with a commitment to hospitality, property care, and homeowner success. Our team is passionate about building strong relationships, maintaining high standards, and creating experiences that keep both homeowners and guests coming back.

If you enjoy connecting with people, building relationships, and being part of a growing company with an excellent reputation, this is an exciting opportunity to make a direct impact while helping expand one of Southwest Michigan's premier vacation rental management companies.

Position Summary

Juniper Holiday + Home is seeking a driven and relationship-focused Sales Representative Homeowner Acquisition to help grow our portfolio of managed vacation rental properties throughout Southwest Michigan.

In this role, your primary responsibility will be identifying, engaging, and signing new homeowners into Juniper's management program. You'll serve as the face of the company in the community, building trust with property owners and demonstrating the value Juniper brings through its property management, hospitality, and revenue optimization services.

This position is ideal for a motivated sales professional, real estate professional, or highly connected local networker who enjoys building relationships, managing a sales pipeline, and closing deals. You'll work closely with Juniper's leadership team while maintaining ownership of your territory and sales goals.

Key Responsibilities

• Work assigned lead lists, including permit data, FOIA-generated short-term rental owner lists, and Juniper's existing HubSpot pipeline

• Meet with homeowners to build relationships and present Juniper's property management services

• Generate new business opportunities through networking, referrals, local events, and community engagement

• Manage ongoing communication and follow-up with prospective homeowners throughout the sales process

• Maintain accurate and organized records within HubSpot CRM

• Guide homeowners through the sales process from initial contact through signed management agreement

• Consistently maintain a healthy sales pipeline and meet activity goals

• Collaborate with internal teams to ensure a smooth transition once new homes are signed

• Represent Juniper professionally throughout Southwest Michigan and surrounding markets

Required Qualifications

• Proven sales experience with a track record of building relationships and closing business

• Established local network within Southwest Michigan or the ability to quickly develop one

• Strong communication, presentation, and interpersonal skills

• Experience using CRM software or the ability to quickly learn HubSpot

• Highly organized with excellent follow-up and time management skills

• Self-motivated and capable of working independently

• Professional, credible, and comfortable meeting with homeowners in person

• Valid driver's license and reliable transportation

• Ability to travel regularly throughout the assigned territory

Preferred Qualifications

• Active Michigan real estate license

• Experience in real estate, property management, vacation rentals, hospitality, or related industries

• Previous experience with HubSpot or other CRM platforms

• Familiarity with the Harbor Country, Berrien County, and surrounding Southwest Michigan markets

• Established network of homeowners, real estate professionals, or community contacts

What Success Looks Like

• Approximately 50 homeowner contacts per week

• 8-12 homeowner meetings per week

• 2-3 new homes signed into management per month

• Consistent pipeline activity and CRM management

• Strong referral generation and relationship-building within the local market

Territory

This role primarily serves Harbor Country and Berrien County, including:

• Union Pier

• New Buffalo

• St. Joseph

• Stevensville

Additional growth opportunities exist throughout South Haven, Michigan and Michigan City, Indiana.

Compensation, Benefits & More

Compensation: $25,000 - 28,000 base salary with an on on-target earnings of 84,000 annually

Bonus Opportunity:

• Commission paid on new homes signed into management

• Additional performance incentives available

• High performers can earn $100,000+ annually

Benefits:

• Paid time off

• Mileage reimbursement

• Monthly phone stipend

Job Type: Full-Time

Location: Union Pier, Michigan Area (field-based travel required)