Product & Engineering Software Engineer or Senior Software Engineer Chicago, IL​/Remote

Software Engineer or Senior Software Engineer

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

Hard work, high standards, real impact. Obie is on a mission to redefine real estate insurance, and we need motivated full-stack engineers (React, Graph

QL, Node.js) to help us build. This isn’t just a coding job—it’s an opportunity to shape our product, our team, and our company from the ground up. The work will be fast, challenging, and deeply rewarding. If you're looking for a place where your code actually matters, read on.

• We show up for each other, in the quality of our work, and in the simplicity of our solutions.
• Make an impact. We’re growing fast, and this role offers the chance to influence key decisions and take on leadership opportunities.
• Move fast, ship faster. We deploy multiple times per day and ship features in days, not months. If you love speed and iteration, you’ll thrive here.

• Build. Ship. Improve. Write high-quality, high-performance, maintainable code.
• Own your work—write tests, review code, and keep tech debt in check.
• Architect and develop applications, databases, and APIs that drive our platform.
• Collaborate across teams to solve real business challenges.
• Power our partnerships by building and scaling APIs that turn archaic systems into elegant, real-time integrations.
• Build dashboards that our customers and agents rely on daily to make sense of their life and work.
• Automate workflows so Obie employees can move faster and focus on high-value work.
• Help us go to market with new insurance products and state expansions in record time.

• Experience with React, Node.js, Type Script, relational databases, testing frameworks, and CICD tools.
• A bias for action—strong ability to prioritize, multitask, and deliver.
• Agile mindset—comfortable with fast iterations and quick pivots.
• Clear, effective communication, especially in a distributed team environment.
• 2+ years of experience in software development.
• Degree in CS or related field preferred—but talent and drive matter more.

🚀 This role is not for everyone. It’s for builders, problem-solvers, and engineers who want their work to mean something. If that’s you, let’s talk.

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 Linked In to see how people interact with our brand and product.
• Meet us and get to know Obie
  You’ll first talk to Kara on a 30-minute call for a mutual fit conversation. We’ll talk about your experience, what you’re looking for, and answer any questions about Obie’s team, culture, and product.
• Technical Discussion (45 minutes)
  Next, you’ll meet with Engineering Leader Thomas Baker, and another member of the team, for a deep dive into your technical skills. Expect a conversation about your experience, approach to problem-solving, and key technologies.
• Take-Home Coding Challenge
  You’ll complete a small…