Account Executive

HUB International•Bozeman, MT

46d

About The Position

ABOUT PROPER INSURANCE 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

Requirements

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

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