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Director of Direct Sales - Roamly image - Rise Careers
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Director of Direct Sales - Roamly

About Roamly

Roamly is the first full-stack insurtech for travel enthusiasts with an embedded offering that brings modern-day RV insurance to make owners'

vehicles 'rent ready.' Roamly provides a suite of unique digital insurance products that eliminate the commercial use exclusion clause that prohibits online renting activity. Roamly enables marketplaces to embed and offer a broad array of insurance products – such as rental insurance, trip and travel insurance, and pet insurance, among other offerings – directly to customers through simple booking flows. Additionally, the insurtech provides personal and professional insurance products to peer-to-peer and marketplace businesses. For more information, visit www.roamly.com.

About the Role

You oversee all strategic sales and churn intervention functions under the Roamly brand which include P&C personal & surplus/commercial lines sales of RV Insurance policies and Roamly RAC partnerships. In addition you will be in charge of supplemental sales functions that fall under the Roamly sales teams purview including Stays Supply. You will advocate internally to influence our product decisions, roadmap, and help us ensure that we provide the best experience possible. As the Senior Director of Direct Sales, you will be one of the frontline heroes for our adventurous community.

For this role we are seeking candidates who are able to work in our Austin, TX Headquarters. This role is not eligible for remote-work.


Your work at Roamly:

  • Develop sales strategies to acquire new insurance clients managing them through the entire sales cycle
  • Work closely with the Head of Partnerships and Senior VP of Sales to oversee the development of all new sales strategies relating to Roamly RAC Platform sales (ex. Dealership Sales)
  • Work closely with the Senior VP of Sales to oversee the development of Stay’s Supply sales function
  • Build and maintain valued, trusted relationships with clients which includes a deep understanding of their needs and monitor their preference
  • Lead, mentor and motivate a sales team to improve their performance, as well as hiring and training new sales representatives
  • Self-starter in identifying market opportunity, scoping an enterprise-wide strategy and lead implementation with cross-functional buy-in
  • Keep abreast of competition, competitive issues, and products and services in the insurance space
  • Drive results - gross written premium and both personal lines commercial lines policy growth
  • Oversee all churn intervention strategies for the Roamly personal & commercial lines policies

What you will bring to the table:

  • Minimum 8 years of years of experience leading people and/or leaders, preferably within a sales capacity
  • Minimum 4 years of selling P&C insurance products
  • Current Property & Casualty Agent License and be able to maintain licensing in all states
  • A college degree is preferred but not required
  • A self-starter mentality with a desire to solve problems and identify and present new client opportunities using data and analytics
  • Excellent organization, prioritization, and time management skills
  • Strong sales mentality with proven track record of growing, managing and maintaining a book of business
  • Professional level written and oral communication skills
  • Effective analytical and problem-solving abilities
  • Quote and sell Personal Lines & Commercial insurance to customers over the phone (both inbound and outbound calls) and via email
  • Ability to comfortably manage a high volume of inbound calls and outbound calls
  • Excellent oral, analytical and written communication skills
  • You are a go-getter and a self-starter. You are efficient and organized when handling a variety of tasks with the ability to think outside the box to promote our Do The Right Thing company value.
  • You love to be counted on and are highly dependable. Reference checks should reveal no attendance patterns
  • Ability to perform at a high level and manage stress and workload
  • Strong commitment to results
  • A passion for sales and a personality that thrives in a fast-paced environment where change and challenge happen often!
  • Live, Promote, and Appreciate our company culture. You align with Outdoorsy’s mission, and are self-aware and maintain a positive attitude in all situations


  • 401K
  • Discretionary PTO
  • Health, vision, and dental insurance
  • Equity in the company
  • However, the compensation package is usually the second reason people choose to join a startup. The primary reason is they want to experience the growth that comes from pouring your heart and soul into building something people love and winning a market. That's what we do at Roamly.

We continue to have our home and headquarters in Austin, Texas, but we have embraced a distributed model of working to reach the best talent in the United States and globally. While some roles may require proximity to our Austin office, roles based outside of our Austin office can sit in any of the following 21 US states: AR, AZ, CA, CO, FL, GA, IL, IN, MN, MO, MT, NV, OH, OK, SD, TN, TX, UT, VA, WA and WV. Please only apply if you are able to live and work full-time in one of the states listed above. State locations and specifics are subject to change as our hiring requirements shift.

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, selection for training, the use of all facilities, and participation in all company-sponsored employee activities.

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CEO of Outdoorsy
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Jeff Cavins
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Outdoorsy's mission is to restore our relationship with the outdoors and each other. We empower our guests to get outside and experience life's best moments while ensuring everyone has access to safely enjoy outdoor travel.

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