Sell property, casualty, homeowners, auto, RV, and other insurance products through consultative customer engagement. Manage inbound and outbound leads, quote policies, gather underwriting information, explain coverage, convert prospects, cross-sell and upsell, and guide customers through binding. Maintain accurate CRM documentation and stay current on insurance products, systems, and carrier platforms while delivering professional customer service.
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.
Requirements
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.
Benefits
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.
Similar Jobs
Artificial Intelligence • Fintech • Insurance • Marketing Tech • Software • Analytics
Handles inbound calls and warm leads, consults customers on property and casualty insurance needs, recommends appropriate coverage, and converts prospects into policyholders. The role includes paid licensing and training, customer communication, sales closing, remote work, and compliance with state licensing requirements. Employees must work designated weekday and weekend shifts and maintain a suitable home office with high-speed wired internet.
Top Skills:
Cable InternetDsl InternetFiber InternetPc
Cloud • Fintech • Software • Business Intelligence • Consulting • Financial Services
The Tax Manager will oversee tax consulting for partnerships, manage client engagements, mentor staff, and ensure compliance with tax regulations.
Top Skills:
Tax-Related Software
Cloud • Fintech • Software • Business Intelligence • Consulting • Financial Services
Lead client advisory services for skilled nursing facilities, driving financial insights and operational guidance while mentoring teams and managing relationships.
Top Skills:
Bill.ComIntaactNetSuiteQuickbooks Online
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
