Middle Insurance Specialist

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.

Brief Summary of Role

Obie’s insurance production team is seeking a licensed insurance producer to help drive growth and expand our book of business. We’re looking for an innovative, motivated, and results-driven insurance professional who thrives in a fast-paced environment and brings strong insurance knowledge, proven sales skills, and a customer-first mindset.

What you'll Do

• ​​Take in sales leads, determine which type of policy will be needed, and effectively quote business (NO COLD CALLING)
• Utilize Salesforce to track and manage new sales leads and metrics
• Proactive and diligent client follow-up
• Follow Underwriting guidelines and carrier SOPs
• Mastery of diverse policy types—including Builders Risk, Landlord (short-term/Long-term), commercial property, General Liability, and Flood

What you'll Bring

• Active Property & Casualty License
• 2 or more years of insurance sales experience (Commercial, E&S, Builders Risk, or personal lines home/auto highly preferred)
• Familiarity with Salesforce preferred
• Ability to generate leads & close business
• Highly organized and detail-oriented
• Propensity and passion for delivering world-class customer service

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 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, Insurtech Amplified Podcast

1. Meet us and get to know Obie
   You'll first talk to Kara 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.
2. Meet the hiring manager
   Next, you'll have a 45-minute video interview with the hiring manager, Glen Roberts, to assess your technical skills for the role.
3. Complete a Project Exercise
   This role requires requires P&C insurance knowledge and strong communication skills, so we'll 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!
4. 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 a leading insurance platform for real estate investors, combining proprietary technology with a modern insurance experience to simplify Home and Landlord insurance. Today, we serve customers nationwide through direct digital experiences, a growing network of insurance agents, and strategic partnerships with lenders, property management platforms, and real estate technology companies.
As part of The Baldwin Group, one of the nation's leading insurance distribution platforms and a USA TODAY Top Workplace, we're combining the agility of a fast-growing technology company with the scale, resources, and career opportunities of a larger organization as we shape the future of investment property insurance.

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:

• Comprehensive health, dental, vision and life insurance
• Flexible paid time off
• Retirement savings plan with company match

Obie values transparency and data driven decision making, enabling us to have a consistent and equitable approach to compensation. We are informed by a benchmarking tool which provides real time compensation data allowing us to regularly check our salary ranges against other venture backed companies and startups within our industry. We've provided the full base salary range for this role below, but please note that we typically target the mid point of the salary range to allow room for growth within the role. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc.

During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.