Proper Insurance Services
December 19, 2023
Bozeman, Montana
Job Type
Annual Salary: $140,000 - $170,000 based on experience and achievement



Largest Managing General Agent in the Vacation Rental Insurance Market, Coverholder with Lloyd’s of London 

Proper Insurance Services is a managing general agent and coverholder at Lloyd’s of London and has been in business since 2014. We provide 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’re hiring a smart, energetic Business Attorney who can expertly manage legal intricacies and oversee regulatory compliance to work closely with the executive management team to ensure sound legal decision-making to sustain and elevate our business operations.

You’ll also work closely with sister companies Wister Specialty and Waivo, developing bespoke contracts, coverage analysis, claims and much more.

Why Work With Us? 

This is a dynamic role where you’ll engage in diverse legal tasks, from contract drafting and negotiation to risk assessment, ensuring company-wide adherence to legal standards.

You’ll also be given the autonomy to assist in directing and refining our legal operations, exercising discretion and leveraging expertise to guide decisions, as well as work cross-departmentally, ensuring legal strategies align with our business objectives and customer commitments.

Your Key Responsibilities? 

In this position, you will regularly review and update the company’s compliance with insurance regulations across all 50 states, providing informed legal counsel to management. You’ll also oversee the drafting, reviewing, and negotiation of contracts, ensuring they protect the company's interests and proactively identify legal risks to safeguard the company's operations.

Who Thrives Here? 

If you’re an analytical thinker with a knack for dissecting complex legal scenarios and formulating actionable, sound strategies, and you’re great at working with people in a fast-paced environment, you’ll love working with us.

Are you exploring new career opportunities?

Take the first step and apply today. We are excited to incorporate your legal expertise into our operations.


  • Draft, review, and negotiate a wide range of contracts and agreements to ensure the company's interests are protected.
  • Oversee all corporate governance matters, including ensuring compliance with regulations, managing board meeting preparations, and properly filing legal and regulatory documents.
  • Proactively identify legal risks within the business and offer actionable solutions to mitigate those risks, keeping the company's objectives in focus.
  • Represent or oversee representation of the company in disputes, ensuring the best legal strategies are employed to safeguard the organization's rights.
  • Manage relationships with outside counsel as necessary.
  • Provide regular training and updates to internal teams on emerging legal issues, ensuring all departments operate within legal parameters. Offer day-to-day legal advice to senior management and other key stakeholders.
  • Manage and protect the company's IP assets, including patents, trademarks, and copyrights, ensuring they are properly registered, maintained, and enforced.


  • Degree from an accredited law school with active licensure in at least one U.S. jurisdiction.
  • Experience with business law. Insurance law preferred, with a focus on short-term rental or property insurance matters.
  • Proven experience in drafting and negotiating contracts within the insurance industry and knowledge of insurance regulations across all 50 states.
  • Strong background in managing litigation, especially within the insurance realm, and adeptness at working with external counsel.
  • Demonstrated capability in insurance-specific corporate governance and risk mitigation strategies.
  • Exceptional ability to communicate complex legal matters to diverse stakeholders.
  • A high standard of ethics paired with a history of collaborative work in multidisciplinary teams.


Annual Salary: $140,000 - $170,000 based on experience and achievement


  • Paid time off, sick days, and vacation days
  • Health insurance
  • Dental Insurance
  • Vision Insurance
  • Retirement benefits or accounts
  • Healthcare spending or reimbursement accounts, such as HSAs


  • Our regular business hours are Monday to Thursday, 8 am to 5 pm, and Fridays from 8 am to 4 pm.
  • Flex work core hour schedules are available.