Proper Insurance
January 28, 2024
Bozeman, Montana
Job Type
Annual Salary: Based on performance



Leading the nation in short-term rental insurance, with over 100,000 policies written in all 50 states.

At Proper Insurance Services, we provide property managers and vacation rental owners with insurance policies that cover both commercial and personal use in one policy. Backed by Lloyd’s of London and endorsed by Vrbo as its premier vendor for comprehensive short-stay rental property and liability insurance, we proudly insure over 100,000 policies in all 50 states.

Our team is a collaboration of individuals with over 50 years of experience in niche insurance. Together, we’ve created this product with one thing in mind - the short-term stay property owner.

When you join us, you will become an important member of our 5-star team, helping vacation rental and property managers acquire a superior solution to their insurance needs with true peace of mind.

We are looking for talented individuals to join our growing company.


Don't miss this chance to combine your strong work ethic, empathy, and passion for sales in a growing company that values innovation, collaboration, and a friendly work environment.

We’re looking for a dynamic Account Executive who's not just about making a sale but about educating and guiding. If you're someone who can identify the gaps in traditional insurance policies for a short-term rental business and present a better solution, then you might be the one we're looking for.

Why Join Us?

  1. Our Educative Approach: We don't just sell; we educate. Our mission is to guide prospects through the maze of traditional insurance policies, showcasing our industry-leading solutions for their business.
  2. Get Licensed on Us: Not licensed yet? No worries. If you're the right fit, we'll cover your licensing costs.
  3. Growth & Collaboration: We're a growing company that values innovation, collaboration, and a friendly work environment.

Your Role?

  1. Lead Engagement: Engage with leads in your assigned territories, focusing on educating and selling our niche insurance product. With 80% of these leads being inbound, you're already at an advantage.
  2. Networking: Reach out to property managers and real estate agents to generate high-quality referrals, making up the other 20% of your leads.

Who Succeeds Here?

  1. Detail-Oriented Multi-taskers: We value precision and the ability to juggle multiple tasks without missing a beat.
  2. Team Players: A collaborative spirit is key. We believe in building positive work environments where everyone feels valued.
  3. Customer-Centric Minds: Our best candidates are genuinely committed to understanding and addressing our customers' needs.

How does the compensation work?

  1. Rewarding Commission Structure: This is a paid commission position, with earnings based on performance. The commission is paid on both new and renewing business. Top performers can expect to earn well over six figures annually in the first three years.
  2. Career Growth: This isn't just a job; it's a career, building a book business that pays dividends based on longevity.

Ready for a change? We look forward to meeting you and seeing how your operational genius can enhance our service to clients. Apply today!


  • Work leads from start to finish through the sales cycle - first contact, follow-ups, etc.
  • Work directly with underwriting to ensure risk quality and that program guidelines are met.
  • Maintain workflow through accurate updating of CRM, answering emails, and diligent documentation.
  • Educate prospective clients about the benefits of our insurance coverage.
  • Maintain a book of business on new and renewing insurance policies alongside the underwriting and customer support/operations team.
  • Grow territory presence with outreach and building relationships with property managers and real estate agents in that area.
  • Answer phones/emails in real-time, acting with a sense of urgency for your clients and prospects.


  • Industry knowledge and experience in customer service/sales preferred
  • A Property & Casualty Insurance License is required prior to the start date. (If you are not licensed but are a qualified applicant, we will pay to get you certified.)
  • Excellent interpersonal skills and ability to communicate effectively both verbally and in writing
  • A positive attitude and excellent problem-solving skills
  • Competency in Microsoft Suite Applications
  • Confidence when using a phone or computer
  • High-level sales knowledge


Annual Salary: Based on performance

Bonus: Commission - Base Draw ($5,000 guaranteed first 90 days. $3,000 after 90 days) + New & Renewal Commissions (Renewal commission after 12 months) Monthly and Annual bonuses for top performers.


  • Paid time off, such as PTO, sick days, and vacation days
  • Health insurance
  • Life insurance
  • Dental Insurance
  • Vision insurance
  • Retirement benefits or accounts
  • Healthcare spending or reimbursement accounts, such as HSAs, FSAs, and HRAs
  • Short-term disability insurance