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 analyzing data to inform business strategies
• Detail-oriented with strong organizational and time management skills
• Proficient in Salesforce
  
  

Nice To Haves

• 5+ years of proven experience in commercial insurance sales and/or customer retention
• Relevant insurance certifications (e.g., CIC, CPCU)
• Experience working with MGAs, MGUs, Bookrolls, or in a similar role within the insurance industry.
  
  

Interview Process

At Obie, transparency is core to our interview process. We focus on open communication and a positive experience; no trick questions—just honest conversations about your skills and aspirations.

To help you prepare, please familiarize yourself with these resources before moving forward:

• Our company’s blog to learn more about the the market we serve and the information our customers value.
• Check out our LinkedIn to see how people interact with our brand and product.
• Press and Podcast features like Inc 5000, TechCrunch, Innovate State, Uncontested Investing Podcast, Insuretech Amplified Podcast.
• Meet us and learn about Obie
  
  

You'll first talk to Mary on a 30 minute call to determine whether we’re a good fit for one another. You’ll learn more about Obie and have the chance to ask about our company, team, culture, and product.

• Meet the hiring manager
  
  

Next, you'll have a 45-minute video interview with the hiring manager to assess your technical skills for the role.

• Project Exercise
  
  

This role requires communication, negotiation, and analytical skills so we'll also present you with a short exercise to complete to provide you a chance to flex those muscles. You will be able to complete this exercise on your own time, so please be thorough and use the resources available to you. More on this when you get there!

• Meet the team
  
  

Since you'll be joining a close-knit team, we'll ask you to meet other people in the company so we get to know each other a bit better.

Moving Forward With Obie

Obie is leading the future of real estate investment protection, securing over $25 billion in coverage for thousands of policyholders nationwide. Backed by $39 million in funding and recognized as a top workplace by Built In and Inc., we’re committed to driving progress for our customers and team. Through advanced digital tools, a trusted agent network, and strategic partnerships, Obie provides real estate investors the insurance coverage they need to move forward confidently.

Obie Has You Covered

Being in the insurance industry, we understand the importance of comprehensive benefits for you and your family. These are just some of the benefits and perks we provide:

Competitive salary

Flexible time off with an encouraged minimum time away to support a healthy work-life balance

12 weeks of Paid Parental Leave

Great health, dental and vision coverage

Life Insurance

Flexible Spending & Health Savings Accounts

Stock Options

401k match

Pet Insurance Reimbursement

Health and wellness benefit

Equipment budget - everything you need to do your best work

Professional development support

Summer hours

The Pay Range For This Role Is

50,625 - 84,375 USD per year(US)