Software Engineer or Senior Software Engineer, Obie
$100-180k
More information about location
Insurance for landlords and real estate investors
Be an early applicant
Insurance for landlords and real estate investors
101-200 employees
Be an early applicant
$100-180k
More information about location
101-200 employees
Company mission
To provide a simple, affordable, and transparent insurance experience for landlords and real estate investors.
Role
Who you are
- If you're passionate about driving change and eager to impact the real estate and insurance market, Obie is the place for you
- 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
What the job involves
- 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
- 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
- You'll 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
Application 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 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
- 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
Our take
Obie is transforming how landlords across the US access insurance for their properties. Through its tefch0druiven platform, landlords can easily get instant quotes, connect with the right insurance provider, and secure coverage - all without the hassle of paperwork or complicated processes. The company insurers over $25M in properties across all 50 states, offering a simple and affordable alternative to traditional insurance.
Focusing on small-to-medium-size rental properties, Obie addresses the challenges landlords face with poor pricing and inadequate coverage. By leveraging technology, the company provides customized, industry-best rates and a straightforward online experience.
Now the company plans to evolve further by utilizing its data and client base to potentially become its own insurance carrier. With strong funding to its name, the company is well-positioned for continued growth and to reshape the future of landlord insurance.
Steph
Company Specialist at Welcome to the Jungle
Insights
26% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
May 2023
$25.5m
SERIES B
May 2021
$10.7m
SERIES A
Total funding: $39.2m
Company benefits
- Medical, Dental, Life, Vision
- 401(k) Matching
- Pet Insurance
- Paid Parental Leave
- Hotel Discounts
- Telehealth
- Flexible Time Off
- L&D Stipend
- Wellness Stipend
- Benefit Support Tools
Company HQ
West Loop, Chicago, IL
Leadership
Ryan Letzeiser
(Co-Founder & CEO)They studied at Clemson University before working as a Real Estate Investment Analyst, and becoming an Investment Associate at Hudson Capital Investments. They joined MAC Properties in March 2015 as a Managing Member in 2015, before co-founding Obie in July 2018.
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