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, CA, DC, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NY, NC, OH, OR, PA, SC, SD, TN, TX, UT, WA, WI

Brief summary of role:

As a Technical Project Manager you will play a key role in building out the products and infrastructure to grow our business. The Technical Project Manager is a varied and fast paced role offering every opportunity to demonstrate your relentless attention to details, strong communication skills, tools for organization, and pragmatic project manager talents. Although we don’t have a rigid experience requirement, this is a junior-level position best suited to someone with a couple years' experience in a TPM or related role.

We want to work with people who are humble enough to recognize they don’t know everything and curious enough to ask questions, as well as those who like to get things done and have a talent to unblock tasks while building deep organizational relationships along the way.

What you'll do:

• You are all about the details and have strong writing skills: You will work to manage project objectives, scope, budget, and timelines with product managers, program managers, and appropriate department stakeholders. You will identify, plan, and communicate project risks and roadblocks to the program management team. 
• Jira excites you (and maybe even Gantt charts): You will monitor project progress continuously and make detailed scheduled reports on measurable items, such as milestones and deliverables. You will communicate proactively with all involved personnel to provide encouragement, identify problems, create solutions, and implement efficiency improvements. 
• You understand the importance of requirements: You will oversee research materials as needed before and during projects by talking with team members, managers, in-house insurance experts, and channel partners in meetings or working sessions. You will monitor and provide hands-on recording, tracking, and reporting for meetings, project activities, and action items. 
• You can change the time on your VCR: It's in the title, but you should have a fairly strong technical background. You will work closely with our Engineering team and need to understand high level technical constraints and opportunities of our tech stack, and implications of project tasks. You'll assist in leading and supporting the Engineering and Product teams with the delivery of projects and initiatives across the company. 
• 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 of working as a successful Technical Project Manager or similar. 
• Strong analytical, organizational, and project management skills. 
• Excellent interpersonal and communication abilities. Flexible, adaptable, and solutions-oriented. Passionate about continuous improvement and sharing best practices. Proactive with keen attention to detail and follow-through.
• We are a crossroad between tech and insurance which means you will be working in varying environments and will need to be able to adapt to situations. Being able to work async is just as important as being able to coordinate a monthly business review across departments.
• You will assist in driving vision and purpose in varying pillars of the business.
• You should be able to act as a leader of persuasion towards aligned team vision and purpose.
• Ability to balance competing priorities in a fast-paced environment, and push back on leaders and stakeholders when necessary. 
• Strong sense of urgency to drive projects to completion. 
• Working knowledge of GitHub products, Atlassian suite, and other industry standard project management tools. 
• Able to work independently while maintaining transparency and collaboration with the rest of the team. 
• Maintain composure and tact under pressure. 
• Ability to multitask and to manage multiple priorities across multiple teams that are geographically distributed. 
• Attention to detail for thorough quality assurance and product testing. 

Nice to haves:

• Experience working on projects at scale and fast paced (preferably 100+ employees) in a Saas, Payments, or Insurtech 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:

• 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 Rebecca 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.

2. Meet the hiring manager
Next, you'll have a 45-minute video interview with the hiring manager to assess your technical skills for the role.

3. Complete a Project Exercise
This role requires strong planning, collaboration, and leadership skills, so we’ll ask you to complete a short exercise. You can take your time and use the resources available. We’ll assess your problem-solving abilities, writing skills, empathy, demeanor, and how well you apply key project management strategies. More details will come when you reach this step!

4. 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.

More about 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