Insurance Specialist II

About Obie:

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 searching for a licensed insurance producer for our venture and Y Combinator-backed insurance and risk management start-up.  We are looking for an innovative, bright, motivated and hard-working individual to join our team to help us accomplish our mission of combining insurance know-how, innovative technology and world-class service to delight our customers.

What you'll do:

• Take in sales leads, determine which type of policy will be needed, and effectively quote business
• Track and manage new sales leads and metrics
• Proactive and diligent client follow up
• Service existing accounts
  

What you'll bring:

• Active Property & Casualty License
• 2 or more years of insurance sales experience (commercial 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 Mary 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.

2. Meet the hiring manager

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

3. Complete a Project Exercise

This role requires P&C insurance knowledge and strong communication skills, so we'll present you with a

short exercise to complete to provide you with 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.

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:

• 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.