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 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 and make risk-based decisions that maintain the profitability and integrity of the book of business
- Review property inspection reports, photographs, and related documentation to identify hazards, condition concerns, eligibility issues, and discrepancies from information provided during the application process
- Determine appropriate underwriting action based on inspection findings, including identifying when additional information, remediation, policy changes, cancellation, or non-renewal may be necessary in accordance with underwriting guidelines
- Document inspection findings and underwriting decisions clearly and consistently within applicable systems
- Monitor relevant KPIs and book performance within your assigned territory, react to emerging indicators, and recommend solutions when needed
- Apply underwriting guidelines and use sound judgment when evaluating property risks, escalating risks or exceptions outside of established authority when appropriate
- Use your underwriting knowledge to identify procedural efficiencies and continually evolve underwriting best practices
- Collaborate cross-functionally to identify trends or recurring issues found through inspections and other underwriting activity that may impact risk selection, guidelines, or portfolio performance
- Collaborate with TPAs to help manage and monitor post-loss activity
- Contribute to a culture of ownership, collaboration, positive reinforcement, and accountability to yourself, the team, and the company
What you'll Bring
- 2+ years of experience in P&C property underwriting
- Experience reviewing property inspections and using inspection findings to make or recommend underwriting decisions
- Strong understanding of property risk characteristics, hazards, condition concerns, and their impact on eligibility and underwriting decisions
- Strong analytical skills, including the ability to assess performance and P&L within a book of business
- Strong attention to detail and the ability to identify inconsistencies across applications, policy information, inspection reports, photographs, and supporting documentation
- Experience and comfort using a variety of tools, including Excel, Google Workspace, and policy management systems
- Excellent verbal and written communication skills with the ability to clearly document and communicate underwriting decisions
- Sound judgment and confidence making decisions independently while recognizing when escalation is appropriate
- Adaptability in a fast-moving, evolving environment with the ability to manage multiple priorities 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:
- 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. - Meet the hiring manager
Next, you'll have a 45-minute video interview with the hiring manager, Melissa Papelbon, to assess your technical skills for the role. - Complete a Project Exercise
This role requires strong underwriting, collaboration, communication, and analytical skills, so we’ll ask you to complete a short exercise. You can take your time and use the resources available. 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! - 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 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.