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[Remote] Insurance Account Executive (Remote US)

Remote, USA Full-time Posted 2026-06-12

Note: The job is a remote job and is open to candidates in USA. Roamly Insurance Group, a subsidiary of Outdoorsy Holdings, Inc., is an innovative Insurtech focused on enhancing the customer experience for travel enthusiasts. The Insurance Account Executive will engage with customers to provide personalized insurance solutions and drive sales through effective lead conversion and consultative sales techniques.

Responsibilities

  • 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

Skills

  • 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 adaptable to varying customer personality types and situations
  • 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

  • Uncapped commissions
  • Amazing Front Line Leaders to support you throughout your onboarding and beyond
  • Opportunity to earn equity compensation
  • We offer a full health and welfare benefits package
  • A 401(k) match
  • Flexible Paid Time Off
  • RV rental discounts
  • A company culture that values a healthy balance between work and adventure
  • Uncapped commission and regular SPIFFs

Company Overview

  • Roamly is a telecommunications company that provides talk, text, and data across the globe with savings on roaming charges. It was founded in 2012, and is headquartered in Richmond Hill, Ontario, CAN, with a workforce of 51-200 employees. Its website is http://www.roamly.com.
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