Surplus Lines Filing & Compliance Analyst

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 a bright, hard-working individual to assist with the compliance needs of our surplus lines insurance operations. This person will help maintain and manage procedures that ensure regulatory and legal compliance in accordance with applicable state statutes and regulations. Those successful in this role will have knowledge and experience in the surplus lines insurance space with passions for leading by example and creating new and different solutions while leveraging technology. 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 Help manage the diligent effort operation and ensure its compliance with each respective state & insurance program Complete surplus lines filings; ensure they are compliant and on time Work with accounting to remit tax and fee payments to the state Assist in compliance needs as it pertains to the insurance operation including but not limited to monitoring, auditing, investigating, and updating policy lifecycle operations and procedures Maintain accurate compliance resources, by state, for underwriting, operations & insurance product Advise on ad-hoc compliance questions from different business units throughout the organization Provide input to operational projects as it pertains to by-state regulatory compliance Assist in overseeing Virtual Assistants from assignment creation to reviewing work What you'll Bring Knowledge of surplus lines laws & regulations 2+ years of P&C insurance compliance experience Surplus lines operations experience Firm grasp on regulatory needs and applicable resources Experience and comfort using a variety of software tools from Excel and G Suite, to policy management and customer relationship management software Excellent verbal and written communication skills Fearlessness and adaptability in a fast-moving, ever-changing environment and ability to work on multiple tasks at once. Self-motivated, analytical, and organized with a strong work ethic. 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 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. Meet the hiring manager Next, you'll have a 45-minute video interview with the hiring manager, Brandon , to assess your technical skills for the role. Complete a Project Exercise This role require ... (truncated, view full listing at source)