Insurance Account Executive (Remote US)

OTE Range: $110,000 - $150,000

About Roamly

Roamly Insurance Group (Roamly), a wholly-owned subsidiary of Outdoorsy Holdings, Inc., is the first full-stack Insurtech for travel enthusiasts. Roamly is where the insurance industry and technology intersect to enhance the customer experience. As a disruptor in the specialty insurance space, Roamly removes traditional technology and coverage barriers by providing innovative protection for underserved markets across recreation lines and global mobility markets. For more information, visit roamly.com.

About the Role

As an Insurance Account Executive at Roamly, you will be a front-line hero for our adventurous community. You will serve as a trusted advisor, assisting both prospective and existing clients in obtaining insurance coverage for homeowners, auto, RV, and various other products.

With uncapped commissions and amazing Front Line Leaders to support you throughout your onboarding and beyond, you are truly set up to absolutely crush your OTE and grow your career!

Key Responsibilities

Customer Engagement & Consultative Sales

• Engage customers using a consultative sales approach to understand their insurance needs and recommend personalized solutions across property, casualty, and personal lines.
• Proactively identify opportunities for cross-selling and up-selling, and assist customers in transitioning between Roamly and third-party insurance carriers when appropriate.
• Clearly explain coverage options, policy terms, and insurance processes in a way that’s easy for customers to understand.

Lead Conversion & Sales Execution

• Drive lead conversion through high-volume outbound outreach and responsive handling of inbound inquiries.
• Manage the complete sales process—from quoting insurance products using Roamly’s proprietary tools, to gathering underwriting information, and guiding customers through to policy purchase and binding.

Tools, Documentation & Compliance

• Maintain accurate and timely documentation of customer interactions and follow-ups using Close.AI.
• Stay current on all available insurance products, systems, and carrier platforms to deliver informed, high-quality service and support.

What We're Looking For

• Experience & Licensing: A minimum of one year of Property and Casualty Insurance experience is preferred, specifically with a brokerage that handles multiple carriers. A Property and Casualty License is preferred but not required, as we are committed to helping you with all licensing and renewals.
• Customer-Focused: You are a detail-oriented individual with a strong commitment to providing the best possible service, and you approach every interaction with patience, empathy, and professionalism. You are adaptable to varying customer personality types and situations
• Collaborative: You are eager to work in a fast-paced, team environment where you can manage your workload effectively and maintain a positive attitude.
• Proactive & Organized: You have a strong commitment to achieving results, with effective time management and a high level of performance under stress. You also possess good data entry skills and can navigate websites with ease.
• Communication Skills: You have good written and verbal communication skills, are self-aware, and maintain a positive attitude in all situations
• Technical Skills: You have a proficient working knowledge of G-Suite and Microsoft Office products.
• Cultural Alignment: You live, promote, and appreciate our company culture, and align with Outdoorsy's mission of empowering adventure.

Why You'll Love Working Here

• Growth Opportunity: Join a company in its early stages and help build its foundation for success.
• Competitive Compensation: Receive a competitive salary with uncapped commissions.
• Equity: Opportunity to earn equity compensation.
• Comprehensive Benefits: We offer a full health and welfare benefits package, a 401(k) match, and flexible Paid Time Off.
• Work-Life Balance: Enjoy RV rental discounts and a company culture that values a healthy balance between work and adventure.

Compensation & Schedule

• Base Salary: The base salary for this position is $40,000, with an On-Target Earnings (OTE) of $110,000 - $150,000.
• Commission: Uncapped commission and regular SPIFFs.
• Schedule: This is a full-time position.