Engineer I or II

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

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

How We Show Up as a Tech Team

• On the Obie Tech Team, 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.

What you'll Do

• 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.

What you'll Bring

• Experience with React, Node.js, TypeScript, 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.

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 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.
2. Technical Discussion (45 minutes)
   Next, you’ll meet with Engineering Leader Jonathan Watson, 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.
3. Take-Home Coding Challenge
   You’ll complete a small application using React and Node.js.
4. Live Pairing Session (90 minutes)
   You’ll walk through your coding challenge with a few engineers and tackle additional technical concepts not covered in the take-home. This is also a chance to see how we work and collaborate.

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:

• Competitive salary
• Flexible time off with an encouraged minimum time away to support a healthy work-life balance
• 12 weeks of Paid Parental Leave
• Great health, dental and vision coverage
• Life Insurance
• Flexible Spending & Health Savings Accounts
• Stock Options
• 401k match
• Pet Insurance Reimbursement
• Health and wellness benefit
• Equipment budget - everything you need to do your best work
• Professional development support
• Summer hours

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.