Account Executive

Account Executive

Proper Insurance is the national leader in short-term rental (STR) insurance, with over 100,000 policies written across all 50 states. As a Coverholder at Lloyd's of London and the endorsed insurance provider for Vrbo, we offer vacation rental owners a single, comprehensive policy covering both commercial and personal use—a solution that traditional carriers simply cannot match.

Founded in 2014 and headquartered in Bozeman, MT, we have grown from a two-person operation to a team of 100+ and continue to expand at an accelerated pace. The short-term rental market is one of the fastest-growing segments in hospitality and real estate, and Proper Insurance sits at the center of it.

The Opportunity

This is a rare chance to build a career—not just hold a job. As an Account Executive at Proper Insurance, you will develop an exclusive book of business in an assigned territory, earning commissions on both new and renewing policies. Because this market is still emerging and largely underserved, the growth ceiling is high for producers who are willing to put in the work.

Approximately 80% of your leads will be inbound, giving you a meaningful head start. The remaining 20% comes from proactive outreach to current clients, property managers and real estate professionals—relationships that, once established, generate high-value referral pipelines.

Compensation & Benefits

Top performers consistently earn well over six figures annually within their first three years. Compensation is structured as follows:

• Base Draw: $5,000/month guaranteed for the first 90 days; 100% Commission after with a draw being paid bi-weekly.
• New Business Commission: Paid on every policy written in your territory
• Renewal Commission: Earned beginning at the 12-month mark—your book compounds over time
• Performance Bonuses: Quarterly bonuses available for top performers

Additional benefits include:

• Comprehensive health, dental, vision, and life insurance
• HSA, FSA, and HRA options
• Short-term disability coverage
• 401(k) retirement plan
• Flexible PTO, sick days, and all major holidays off

Responsibilities

• Manage the full sales cycle from first contact through close, including follow-up cadences and CRM documentation
• Educate prospective clients on the gaps in traditional insurance policies and present Proper's purpose-built STR solution
• Coordinate with underwriting to ensure submissions meet program guidelines and risk quality standards
• Maintain and grow a book of business across new and renewing policies in partnership with the operations and customer support teams
• Develop territory presence through outreach to property managers and real estate professionals
• Respond to client and prospect inquiries by phone and email with a strong sense of urgency

Qualifications

• Property & Casualty Insurance License (required prior to start date). If you are not yet licensed but are otherwise a strong candidate, Proper will cover the cost of your licensing preparation and exam.
• Prior experience in sales or customer service, ideally in insurance, real estate, or a related field
• Strong verbal and written communication skills with the ability to explain complex products clearly
• High attention to detail and the ability to manage multiple active leads simultaneously
• Proficiency with Microsoft Office; comfort navigating CRM platforms and communication tools
• A collaborative, coachable mindset and a genuine commitment to client outcomes

Who Thrives Here

Our most successful Account Executives are self-directed and motivated by ownership. They take pride in being experts in a niche most people have never heard of, and they find satisfaction in guiding clients to a genuinely better insurance solution. They are flexible to changes that come with a fast growing company. If you are energized by building something, comfortable in a performance-driven environment, and eager to be part of a growing company in a market that is still defining itself, this role is worth a serious look.