Roamly

Role Description 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. Qualifications - 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. - 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 eager to work in a fast-paced, team environment where you can manage your workload effectively and maintain a positive attitude. - You have a strong commitment to achieving results, with effective time management and a high level of performance under stress. - You possess good data entry skills and can navigate websites with ease. - You have good written and verbal communication skills, are self-aware, and maintain a positive attitude in all situations. - You have a proficient working knowledge of G-Suite and Microsoft Office products. - You live, promote, and appreciate our company culture, and align with Outdoorsy's mission of empowering adventure. Benefits - Join a company in its early stages and help build its foundation for success. - Receive a competitive salary with uncapped commissions. - Opportunity to earn equity compensation. - We offer a full health and welfare benefits package, a 401(k) match, and flexible Paid Time Off. - 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.

• 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. • 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. • 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.

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.

About Roamly Roamly is a leading provider of innovative, specialty insurance solutions purpose-built for the modern mobility and marketplace travel economy.  As a Lloyd's Coverholder and AI-first insurance innovator, Roamly delivers a robust platform, deep carrier partnerships, and an expanding ecosystem that empowers consumers, professional fleet owners, and marketplaces to unlock new revenue streams while reducing risk. Our technology harnesses AI, advanced automation, and embedded distribution to power tailored coverages for recreational vehicles, carsharing, and other emerging mobility models—covering everything from underwriting and claims to compliance, data analytics, and real-time risk management. Learn more at www.roamly.com. About the Role As an Insurance Service Agent at Roamly, you will be a front-line hero for our adventurous community. You will be the core resource for educating customers on RV insurance and helping them with their policy needs. We are looking for individuals who are excited to be a "change agent" within the company and can maintain high performance in a rapidly evolving landscape. Your work will be crucial in ensuring the best possible customer experience and will directly influence our product decisions and roadmap. Key Responsibilities - Effectively multitask while taking customer calls and handling email correspondence regarding billing questions, online payments, renewals, and cancellations. - Process incoming policy change requests from customers. - Review policy coverages and issue certificates of insurance, evidence of insurance, or binders. - Retain customers by overcoming objections to cancellation and providing effective solutions. - Upsell ancillary products such as roadside assistance, tire & wheel protection, and pet insurance. - Identify opportunities to cross-sell and transfer new business leads to the sales team.

• Effectively multitask while taking customer calls and handling email correspondence regarding billing questions, online payments, renewals, and cancellations. • Process incoming policy change requests from customers. • Review policy coverages and issue certificates of insurance, evidence of insurance, or binders. • Retain customers by overcoming objections to cancellation and providing effective solutions. • Upsell ancillary products such as roadside assistance, tire & wheel protection, and pet insurance. • Identify opportunities to cross-sell and transfer new business leads to the sales team.

• Effectively multitask while taking customer calls and handling email correspondence regarding billing questions, online payments, renewals, and cancellations in both English and Spanish. • Process incoming policy change requests from customers. • Review policy coverages and issue certificates of insurance, evidence of insurance, or binders. • Retain customers by overcoming objections to cancellation and providing effective solutions. • Upsell ancillary products such as roadside assistance, tire & wheel protection, and pet insurance. • Identify opportunities to cross-sell and transfer new business leads to the sales team.

About Roamly Roamly is a leading provider of innovative, specialty insurance solutions purpose-built for the modern mobility and marketplace travel economy.  As a Lloyd's Coverholder and AI-first insurance innovator, Roamly delivers a robust platform, deep carrier partnerships, and an expanding ecosystem that empowers consumers, professional fleet owners, and marketplaces to unlock new revenue streams while reducing risk. Our technology harnesses AI, advanced automation, and embedded distribution to power tailored coverages for recreational vehicles, carsharing, and other emerging mobility models—covering everything from underwriting and claims to compliance, data analytics, and real-time risk management. Learn more at www.roamly.com. About the Role As a Bilingual Insurance Service Agent at Roamly, you will be a front-line hero for our adventurous community. You will be the core resource for educating customers on RV insurance and helping them with their policy needs. We are looking for a true "change agent"—someone who is excited to help build our processes and thrives in an environment of constant growth. Your work will be crucial in ensuring the best possible customer experience and will directly influence our product decisions and roadmap. Key Responsibilities - Effectively multitask while taking customer calls and handling email correspondence regarding billing questions, online payments, renewals, and cancellations in both English and Spanish. - Process incoming policy change requests from customers. - Review policy coverages and issue certificates of insurance, evidence of insurance, or binders. - Retain customers by overcoming objections to cancellation and providing effective solutions. - Upsell ancillary products such as roadside assistance, tire & wheel protection, and pet insurance. - Identify opportunities to cross-sell and transfer new business leads to the sales team.

OTE Range: $80,000 - $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.