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Licensed Insurance Sales Agent (Remote)

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!

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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$55000 / YEARLY (est.)
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$40000K
$70000K

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

Join the Roamly Team as a Licensed Insurance Sales Agent! At Roamly Insurance Group, part of the Outdoorsy Group, we're on a mission to revolutionize insurance for adventure seekers. Our unique, embedded offerings make RVs rent-ready, and we pride ourselves on providing modern insurance solutions that are just a click away for RV owners and renters. In this exciting role, you’ll educate our community about various RV insurance options, helping them choose the coverage that fits their adventurous lifestyles. You'll be the friendly voice guiding them through the quote and sale process for Personal Lines and Commercial insurance, all while maintaining a positive, solutions-oriented approach. With flexible hours and the chance to work from anywhere, this is the perfect opportunity for a self-starter with a passion for sales. Don’t worry if you’re new to insurance; we welcome motivated individuals eager to learn! Join us in connecting adventurous spirits with the right insurance solutions, and enjoy attractive compensation and benefits, including RV rental discounts and a culture that promotes work-life balance. If you’re ready to be part of something great, we can’t wait to see you apply!

Frequently Asked Questions (FAQs) for Licensed Insurance Sales Agent (Remote) Role at Outdoorsy
What does a Licensed Insurance Sales Agent do at Roamly?

As a Licensed Insurance Sales Agent at Roamly, you'll play a vital role in educating clients about RV insurance options, providing quotes, and facilitating sales for Personal Lines and Commercial insurance over the phone and email. You'll also help cross-sell our suite of RV protection products, connecting customers with the right coverage to enhance their travel experiences.

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What qualifications are needed to become a Licensed Insurance Sales Agent with Roamly?

To become a Licensed Insurance Sales Agent at Roamly, you need a current General Lines Property & Casualty Agent License. While insurance experience is beneficial, we welcome new agents as well. Strong communication skills and a commitment to customer satisfaction are essential for success in this dynamic role.

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What is the work schedule for a Licensed Insurance Sales Agent at Roamly?

Licensed Insurance Sales Agents at Roamly have a flexible work schedule, with core hours falling between 9 AM and 6 PM CST, Monday to Friday. Some weekend availability may be required, allowing for a balance between work commitments and personal adventures.

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What kind of training and support will I receive as a new Licensed Insurance Sales Agent at Roamly?

Roamly is dedicated to the success of our team members. New Licensed Insurance Sales Agents will receive comprehensive training on our products and services, as well as ongoing support from experienced colleagues. We believe in fostering a learning environment that encourages your growth as you embark on your insurance sales career.

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What are the career growth opportunities for a Licensed Insurance Sales Agent at Roamly?

As a quickly growing company, Roamly offers significant career advancement opportunities for Licensed Insurance Sales Agents. By exceeding sales quotas and demonstrating strong performance, you may have the chance for increased base salary and variable compensation, along with potential opportunities for promotions within the organization.

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Common Interview Questions for Licensed Insurance Sales Agent (Remote)
Can you explain your process for educating customers about RV insurance options?

When answering this question, highlight your approach to understanding customer needs and preferences. Discuss how you would simplify complex insurance jargon into easy-to-understand terms and the importance of tailoring your explanations to fit each client's unique situation.

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What strategies do you use for effective lead generation as a Licensed Insurance Sales Agent?

Outline methods like networking, utilizing referrals, engaging in customer outreach via social media, and using targeted online marketing strategies. Emphasize your creativity in generating leads and your commitment to finding new opportunities.

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How do you handle difficult customers or complex questions about insurance policies?

Explain that you maintain a calm demeanor and listen actively to the customer's concerns. Discuss how you would validate their feelings before providing factual information, ensuring that they feel heard and understood throughout the conversation.

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Describe your experience with sales and how it applies to this role.

Even if you’re new to insurance sales, draw from any relevant sales experience. Discuss your enthusiasm for meeting targets, your proactive approach, and and your passion for helping customers find solutions that suit their needs.

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How do you prioritize tasks in a fast-paced work environment?

Demonstrate your organizational skills by explaining your method for assessing priority based on urgency, customer needs, and deadlines. Share any tools or techniques you utilize to stay organized and maintain efficiency.

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What do you think are the key qualities of a successful Insurance Sales Agent?

Focus on qualities such as excellent communication skills, resilience, ability to empathize with customers, a strong work ethic, and a passion for sales. Connect these qualities to how they will help you thrive at Roamly.

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How do you stay updated on insurance trends and regulations?

Express your commitment to ongoing learning by mentioning specific sources you follow, such as industry publications, webinars, or professional groups. Highlight your proactive approach to staying informed about changes that could impact your clients.

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Can you provide an example of how you overcame a sales challenge?

Share a specific example highlighting the challenge you faced, the innovative solution you implemented, and the positive results. Use this opportunity to showcase your problem-solving skills and sales acumen.

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What motivates you to succeed in a sales role?

Talk about both intrinsic and extrinsic motivators, such as the thrill of closing a sale, helping customers protect their investments, and achieving personal and financial goals. Tailor your response to show how these motivations align with Roamly’s mission.

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Why do you want to work as a Licensed Insurance Sales Agent at Roamly?

Here, convey your enthusiasm for Roamly's mission to support travelers and adventure seekers. Discuss how your values align with the company's focus on innovation in insurance and your desire to contribute to its growth and success.

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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
January 2, 2025

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