Underwriter

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 is looking for an innovative, bright and hard-working individual to join our underwriting team to help us accomplish our mission of combining insurance know-how and innovative technology to bring bottom line success for the programs in which we manage. 

Those successful in this role will have property underwriting experience within P&C insurance. Additionally, you’ll be self-motivated and directed. An ability to collaborate is a must, but you will be autonomous and expected to succeed without heavy direction.

What you'll Do

• Facilitate underwriting processes to maintain the profitability and integrity of the book of business
• Ensure your assigned territory is performing profitably by monitoring relevant KPI’s; reacting to indicators where necessary and propose solutions as needed
• Use your in-depth knowledge to find procedural efficiencies to continually evolve our best practices
• Collaborate with TPAs to help manage & monitor post loss activity
• Maintain the existing culture predicated on motivation and positive reinforcement while upholding a standard of accountability to self, team and company
  

What you'll Bring

• 2+ years of experience in P&C property underwriting
• Detail orientation in everything you do: there is a lot of customer and policy information flying by you – having a keen eye here is essential
• Strong analytical skills in assessing P&L within a book of business
• Property inspection underwriting experience
• Experience and comfort using a variety of tools from Excel and G-Suite to policy management systems
• Excellent verbal and written communication skills to problem solve, answer questions, and leave a positive impression
• Fearlessness and adaptability in a fast-moving, ever changing environment and ability to work on multiple tasks at once
• Ability to prioritize competing demands and manage time effectively

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 Skylar 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, Joel Place, to assess your technical skills for the role.
3. Complete a Project Exercise
   This role requires strong underwriting, collaboration, communication, and analytical skills, so we’ll ask you to complete a short exercise to flex those muscles. We’ll assess your problem-solving abilities, written skills, empathy, demeanor, and how well you apply underwriting principles. More details will come when you reach this step!
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 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 starting salary range for this role below. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc.
$60,000 - $80,000 USD per year (US)

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