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
As a Technical Project Manager, you’ll play a critical role in building the products, systems, and infrastructure that power our business. This varied, fast-paced position gives you every opportunity to showcase your attention to detail, communication skills, organizational excellence, and pragmatic project management — while staying aligned with Obie’s vision and quarterly goals.
You’ll collaborate closely with engineers, product managers, and cross-functional partners to ensure tools are built efficiently, testing keeps pace with complexity, and deliverables land on time. If you love dotting every “i,” rallying the right people, and keeping chaos in check, you’ll thrive here.
What You'll Do
- You speak fluent project management: You’ll manage objectives, scope, timelines with stakeholders across both business pillars and engineering pods. You’ll spot risks early and keep everyone in the loop on progress made and aligned on the path forward.
- You can herd cats while juggling flaming torches: You’ll track and report progress from kickoff to delivery, aligning project milestones with company goals all while coordinating with engineers, technical specialists, and PMs.
- You bring order to the sprint shaped chaos: You’ll facilitate sprint planning and ceremonies for an engineering pod, ensuring accountability, clarity, and momentum toward quarterly goals.
- Quality is your love language: You’ll write technical test cases as systems grow in complexity, perform PR reviews, and facilitate QA/business reviews as the SME for your pod.
- You see both the forest and the tech stack: You’ll work closely with engineering to understand high level constraints and opportunities, making sure solutions are scalable, practical, and aligned with our architecture goals.
- You’re the glue that holds the pod together: You’ll build strong lines of communication with stakeholders and maintain transparency on goals while operating independently to get the job done.
- You can work async: You will be able to work independently and make decisions with minimal supervision. You also will be able to demonstrate your excellent communication skills, including the ability to build relationships internally and externally.
What You'll Bring
- Proven track record owning the product lifecycle as a Technical Project Manager or similar role, with deep familiarity in project management principles and Agile frameworks
- Excellent analytical, organizational and project management skills with strong written, verbal, and interpersonal communication
- Flexible, adaptable, and solutions-oriented when facing challenges; skilled at balancing competing priorities in fast-paced environments and pushing back on leaders and stakeholders when necessary
- Ability to multitask and to manage multiple priorities across multiple teams that are geographically distributed, while maintaining transparency and collaboration
- Experience working directly with engineers to understand requirements, limitations, and implementation implications
- Attention to detail for thorough quality assurance and product testing
- Passionate about continuous improvement, learning, and sharing best practices; proactive with strong follow through
- Proficiency with Atlassian suite (specifically Jira) and some experience with Salesforce
Icing on the Cake (nice to haves)
- Experience building products at scale in a tech-forward environment. Some high level technical development experience, and exposure to Data Engineering
- Experience working on projects at scale and fast paced (preferably 50+ employees) in a tech-forward or startup environment
- Basic (or better) experience with modern software development frameworks (SQL, JS, Python, etc.)
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, Regan Smith, to assess your technical skills for the role. - Complete a Project Exercise
This role requires strong planning, collaboration, and communication skills, so we'll also present you with a short exercise to complete to provide you a chance to flex those muscles. You will be able to complete this exercise on your own time, so please be thorough and use the resources available to you. We'll be looking to see your problem solving abilities, writing and communication skills, empathy, general demeanor, and ability to leverage key product management strategies. More on this when you get there! - 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 including 12 week Paid Parental Leave
- Retirement savings plan with company match
- Equity participation opportunities
- Monthly stipends to support a healthy lifestyle and learning and development opportunities
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 our People Ops team regarding your compensation expectations.