Retention Sales Specialist II

At Obie, we don’t just insure properties — we ensure progress. With advanced technology, real-time data, and a vast network of agents and partners, we help real estate investors and landlords get insurance coverage whenever and wherever they need it. Thousands of owners nationwide trust us to be the insurance experts, so they don’t have to be.

Joining our team means embracing a fast-moving environment driven by innovation, collaboration, and constant progress. We learn quickly, iterate often, and celebrate wins together. If you're passionate about driving change and eager to impact the real estate and insurance market, Obie is the place for you.

Our Chicago based employees are hybrid, and expected to be in office on Tuesdays and Thursdays.

While Obie does offer fully remote opportunities for those outside of Chicagoland, we are only currently hiring in the following states: AZ, DC, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NC, OH, OR, PA, SC, SD, TN, TX, UT, WI

Brief summary of role:

We are seeking a dynamic and results-driven Retention Specialist to join Obie.  The ideal candidate will be responsible for managing the end-to-end retention process, including handling objections, converting customers to Obie-branded products, upselling, re-quoting, and conducting research and analysis to support retention strategy and decision-making.

What you'll do:

• Converting to Obie-Branded Products:
• • Proactively engage with customers currently insured with other carriers to present the benefits of our Obie-branded insurance solutions.
  • Lead the conversion process by analyzing current policies and offering tailored alternatives.
  • Ensure a smooth transition by managing all aspects of the conversion, including documentation and communication.
• Objection Handling:
• • Address customer concerns and objections with confidence and expertise, focusing on providing solutions that meet their needs.
  • Utilize a deep understanding of our products and services to overcome common objections related to pricing and coverage.
• Re-quoting at Policy Renewal:
• • Regularly review and re-quote existing customer policies to ensure they are receiving the best coverage and value.
  • Manage the policy renewal process, ensuring timely and accurate communication with customers to retain their business.
  • Proactively engage with customers approaching renewal to discuss any changes in their business that may require policy adjustments.
  • Achieve and exceed conversion targets.
• Upselling and Cross-Selling:
• • Identify opportunities for upselling and cross-selling additional products and services that complement existing customer policies.
  • Work closely with customers to understand their evolving needs and recommend appropriate insurance solutions.
• Researching and Analyzing:
• • Conduct market research and competitive analysis to stay informed about industry trends, competitor offerings, and regulatory changes.
  • Utilize data and analytics to identify trends and opportunities within the commercial insurance market.
  • Provide insights and recommendations to the sales and management teams to support strategic decision-making.
  • Collect and document customer feedback to help refine retention strategies and improve overall customer satisfaction.
  • Assist in the development and execution of customer retention campaigns, including email outreach, phone calls, and personalized follow-ups.

What you'll bring:

• An active Property & Casualty insurance license is required before starting
• 3+ years of proven experience in insurance sales and/or customer retention
• Strong knowledge of insurance products, particularly in property and habitational lines of business and conversion or bookroll sales
• Excellent communication, negotiation, and interpersonal skills
• Ability to handle objections effectively and convert prospects into customers
• Demonstrated success in upselling and cross-selling insurance products
• Proficient in conducting research and a