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Licensed Insurance Sales Agent (Remote US)

Join the Roamly Team!

Roamly Insurance Group (Roamly), part of Outdoorsy Group, is revolutionizing insurance for travel enthusiasts with unique, embedded offerings that make RVs “rent-ready.” We’re the first insurtech dedicated to unlocking modern insurance options for the adventurous spirit—bringing insurance coverage directly to RV owners and renters in a seamless, digital experience. For more, visit roamly.com.

About the Role

As a Licensed Insurance Sales Agent at Roamly, you’ll be at the heart of our mission, educating our community on RV insurance options and helping them select the right coverage for their needs. You’ll advocate for our customers, shape product decisions, and drive our commitment to top-notch customer service. You’ll be the go-to expert for our adventurous community, connecting them with RV insurance solutions that empower them to hit the road with confidence!

Unfortunately at this time we are unable to hire remote agents in the states of California, Colorado, New York and Washington

Key Responsibilities:

  • Quote and sell Personal Lines & Commercial insurance over the phone (inbound/outbound) and via email.
  • Cross-sell Roamly’s suite of RV protection products.
  • Handle a high volume of calls with a positive, solutions-focused approach.
  • Schedule: Flexible hours between 9 AM and 6 PM CST, Monday to Friday, with some weekend availability as needed.

What Makes You a Great Fit:

  • Current General Lines Property & Casualty Agent License required–we take care of all renewals.
  • Insurance experience preferred but not required—new agents are welcome!
  • Excellent oral and written communication skills.
  • A self-starter who’s comfortable managing multiple tasks in a dynamic environment.
  • Strong commitment to achieving results and exceeding customer expectations.
  • A passion for sales with a can-do attitude that thrives in a fast-paced, ever-changing space.

Why You’ll Love Working Here:

  • Growth Opportunity: Join a company in its early stages and be a part of its success.
  • Competitive Compensation: Attractive salary plus equity in one of the industry’s fastest-growing companies.
  • Comprehensive Benefits: Health and welfare benefits, 401(k) match, and flexible PTO.
  • Work-Life Balance: RV rental discounts and an office culture that believes in balancing work with adventure.

Compensation: All licensed agents will start at a base salary of $40,000 and $70,000 OTE with the ability to increase both base and variable after exceeding quota over a rolling 3 months.

At Roamly, we are committed to fostering a culture of inclusion and equality. We celebrate diversity and are proud to offer equal opportunities for all employees.

Ready to Be a Part of Something New? Apply Now!

The expected compensation range for this position is displayed in accordance with potentially applicable laws. The final agreed-upon compensation is based on a number of factors, including but not limited to: individual education, qualifications, prior work experience, and geographic work location. The total annual compensation package may consist of a base salary and bonus dependent upon position.


It is the policy of Outdoorsy Holdings, Inc. to provide equal employment opportunities without regard to race, color, religion, sex, national origin, age, disability, marital status, veteran status, sexual orientation, genetic information or any other protected characteristic under applicable law. This policy relates to all phases of employment, including, but not limited to, recruiting, employment, placement, promotion, transfer, demotion, reduction of workforce and termination, rates of pay or other forms of compensation,

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Average salary estimate

$55000 / YEARLY (est.)
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$70000K

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What You Should Know About Licensed Insurance Sales Agent (Remote US), Outdoorsy

Join the Roamly Team! As a Licensed Insurance Sales Agent at Roamly Insurance Group, a part of Outdoorsy Group, you're stepping into a pivotal role where your passion for travel meets your expertise in insurance. Roamly is transforming the insurance landscape for RV enthusiasts by offering unique, embedded insurance options that make RVs 'rent-ready.' In this position, you'll be at the forefront of educating our community about various RV insurance options, ensuring they find the perfect coverage that fits their adventurous lifestyles. Your role will not only involve quoting and selling personal and commercial insurance but also providing outstanding customer service that truly resonates with our customers. If you love connecting with people and helping them hit the road with confidence, this is the place for you! With flexible hours between 9 AM and 6 PM CST and a culture that values work-life balance and adventure, you'll find that Roamly supports you in achieving both personal and professional goals. Plus, we’re dedicated to your growth—new agents are welcome to apply, and we take care of license renewals. If you're ready to be part of something unique in a dynamic, fast-growing company that celebrates diversity and inclusion, apply now and join us on this journey!

Frequently Asked Questions (FAQs) for Licensed Insurance Sales Agent (Remote US) Role at Outdoorsy
What are the responsibilities of a Licensed Insurance Sales Agent at Roamly?

As a Licensed Insurance Sales Agent at Roamly, you will handle quoting and selling personal lines and commercial insurance via phone and email, manage a high volume of calls, and cross-sell various RV protection products. You'll also educate customers on their insurance options, ensuring they find coverage tailored to their needs. This role is vital in shaping product decisions and maintaining Roamly's commitment to exceptional customer service.

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What qualifications are needed for the Licensed Insurance Sales Agent position at Roamly?

To become a Licensed Insurance Sales Agent with Roamly, you need a current General Lines Property & Casualty Agent License. While prior insurance experience is preferred, it is not mandatory, making this role accessible for new agents eager to start their careers in a supportive environment. Strong communication skills and a passion for sales are also essential.

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What does the work schedule look like for a Licensed Insurance Sales Agent at Roamly?

Licensed Insurance Sales Agents at Roamly enjoy a flexible work schedule, typically working between 9 AM and 6 PM CST from Monday to Friday, with occasional weekend availability. This flexibility allows you to balance your work responsibilities with your personal adventures, reflecting Roamly's commitment to work-life balance.

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What makes Roamly a great place to work for a Licensed Insurance Sales Agent?

Roamly offers a unique opportunity to be part of a fast-growing company dedicated to revolutionizing insurance for the RV community. You'll benefit from competitive compensation, including equity options, comprehensive health benefits, and flexible PTO. The company culture promotes inclusivity and adventure, making it an exciting environment for Licensed Insurance Sales Agents.

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What is the compensation structure for Licensed Insurance Sales Agents at Roamly?

Licensed Insurance Sales Agents at Roamly begin with a base salary of $40,000, with the potential to earn up to $70,000 OTE based on performance. There are opportunities to raise both the base and variable components of your compensation after exceeding quota over a rolling three-month period, rewarding dedication and commitment.

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Common Interview Questions for Licensed Insurance Sales Agent (Remote US)
Can you describe your experience with RV insurance and how it relates to the role of Licensed Insurance Sales Agent at Roamly?

When discussing your experience with RV insurance, focus on any relevant background you have in the insurance industry, including how it helped you understand customer needs. If you're new, mention any research you’ve conducted or your enthusiasm for learning about the unique challenges and benefits of RV insurance as a Licensed Insurance Sales Agent at Roamly.

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How do you prioritize multiple tasks when working as a Licensed Insurance Sales Agent?

In response to this question, share specific methods you use to prioritize tasks, such as using task management tools or setting daily goals. Highlight situations where you successfully balanced multiple customer inquiries and tasks, showcasing your self-starter attitude in the fast-paced role of a Licensed Insurance Sales Agent at Roamly.

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Describe a time you went above and beyond for a customer.

When answering this, be specific about a situation where you provided exceptional service or resolved a customer's issue creatively. This is particularly relevant for the role at Roamly, where customer advocacy is key, so emphasize your commitment to exceeding customer expectations.

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What strategies do you use to handle rejection in sales?

Explain the mindset you maintain when facing rejection, emphasizing resilience and learning from each experience. Describe techniques such as self-reflection or feedback analysis and how these strategies prepare you for the challenges of being a Licensed Insurance Sales Agent at Roamly.

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How familiar are you with the typical RV insurance needs of customers?

Demonstrate your understanding of common RV insurance requirements, such as coverage types and customer concerns. Show enthusiasm for helping customers navigate these options as you support them in their journey as a Licensed Insurance Sales Agent at Roamly.

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What do you think is the most important skill for a Licensed Insurance Sales Agent?

Discuss your belief in effective communication as a key skill. Highlight how exceptional communication can lead to clear understanding of customer needs and ultimately drive sales success, which aligns directly with the responsibilities of a Licensed Insurance Sales Agent at Roamly.

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How would you educate a customer who knows little about RV insurance?

Outline a simple approach to explaining RV insurance, perhaps by breaking it down into essential types of coverage and their benefits. Demonstrate your ability to pivot based on the customer’s questions, underscoring the supportive role of a Licensed Insurance Sales Agent at Roamly.

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What motivates you in a sales role?

Share your personal motivations—whether it's helping customers find the right solutions, achieving sales goals, or the thrill of the sales process. Connect this to how these motivations will enable you to excel as a Licensed Insurance Sales Agent at Roamly.

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Tell us about your experience working in a team environment.

Discuss examples of collaborative projects or experiences where you contributed positively to a team. Emphasize how teamwork enhances customer service and sales performance, elements crucial to the Licensed Insurance Sales Agent role at Roamly.

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Where do you see yourself in five years as a Licensed Insurance Sales Agent?

Outline your ambitions for growth within the insurance industry, whether it's advancing within Roamly or focusing on specialized insurance products. Show your commitment to continued education and development relevant to the Licensed Insurance Sales Agent position.

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Outdoorsy is the largest and safest community-driven marketplace platform that connects RV owners with other campers. They are committed to mobilizing the 56+ million underutilized, idle RVs around the world.

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Full-time, remote
DATE POSTED
April 9, 2025

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