Retention Specialist II

About Obie

At Obie, we are shaking up landlord insurance, making it easily available for landlords and real estate investors both when and where they need it. With a focus on driving efficiency and innovation for our customers and within our team, we’re on the search for new talent that can take Obie to the next level.

At Obie, you’ll collaborate with a diverse team that embraces evidence-based decision making, learns from failure, accepts feedback, and is always prepared to make changes for the better. You’ll be expected to operate with flexibility and leverage your curiosity to drive innovation while collaborating with colleagues across teams and areas of expertise. Our ideal teammates are kind, passionate, committed to excellence and eager to nerd out over the best ways to make Obie even better.

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, CA, DC, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NY, NC, OH, OR, PA, SC, SD, TN, TX, UT, WA, 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

We want you at your best, and won't be giving you any gotcha-style questions - we aren't like that. We want to get to know you, hear about what you're interested in, and learn about what you hope to do in the future.

You Should Familiarize Yourself With These Resources Before Continuing

• Our company’s blog to learn more about the space we’re working in and where we write about landlord insurance.
• Check out our Twitter and LinkedIn to get a glimpse of how people interact with our brand and product.
• Some posts with and about us around the web (Inc 5000, Estate Innovation, Geek Estate Blog, Business Wire, Innovate State)
• Podcast appearances: (RCN Capital - Risk Management & Insuring Your Success In Real Estate, The Ryan Hanley Show, The Real Estate Espresso Podcast)
• Meet us and learn about Obie
  
  

You'll first talk to a member of the People Ops team on a 30 minute call; you won't need to prepare anything in advance. The goal of this conversation is to get to know you and mutually explore if we might be a good fit for each other. You'll learn more about Obie and have a chance to ask any questions about our company, team, culture, and product.

• Meet the hiring manager
  
  

You'll get to have a 45 minute video interview with the hiring manager. This discussion will be more technical in nature to ensure you have the skills needed to be successful in 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.

More About Obie

Founded in 2017, Obie is paving a new path in insurance for landlords and real estate investors. Obie’s goal is to fundamentally change how insurance is bought and sold by building technology and insurance products that increase ease and accessibility for the 17 million residential real estate investors and landlords in the US. Obie offers a superior insurance experience, allowing real estate investors and landlords to obtain the right coverage where it’s most convenient for them, whether that means using our digital quote tools, working with independent agents, or finding us through our integrations with industry partners.

With over 6,000 active policy holders, and over $20 billion in coverage secured, Obie has still barely scratched the surface of its growth potential. That growth is supported by $39 million secured in funding, positioning it perfectly to continue revolutionizing the industry.

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