Associate Account Executive

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, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NC, OH, PA, SC, SD, TN, TX, UT, WI

Brief Summary of Role

Obie's 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 new business
• Assist Account Executives in tracking and managing new sales leads
• Proactive and diligent client follow-up
• Quoting and servicing existing accounts

What You'll Bring

• Active Property & Casualty License
• Sales as a superpower: You excel at speaking with people, solve their problems and help them achieve their goals
• 6 months+ experience in insurance sales (commercial or personal lines home/auto highly preferred)
• Ability to work in a structured and fast paced environment
• 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 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 to assess your technical skills for the role.
3. Complete a Pr