Technical Project Manager

About Obie:
At Obie, we are shaking up landlord insurance, making it easily available for landlords and real estate investors both when and where they need it. With a focus on driving efficiency and innovation for our customers and within our team, we’re on the search for new talent that can take Obie to the next level.

At Obie, you’ll collaborate with a diverse team that embraces evidence-based decision making, learns from failure, accepts feedback, and is always prepared to make changes for the better. You’ll be expected to operate with flexibility and leverage your curiosity to drive innovation while collaborating with colleagues across teams and areas of expertise. Our ideal teammates are kind, passionate, committed to excellence and eager to nerd out over the best ways to make Obie even better.

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. 

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:
We want you at your best, and won't be giving you any gotcha-style questions - we aren't like that. We want to get to know you, hear about what you're interested in, and learn about what you hope to do in the future.

You should familiarize yourself with these resources before continuing:

a. Our company’s blog to learn more about the space we’re working in and where we write about landlord insurance.

b. Check out our Twitter and LinkedIn to get a glimpse of how people interact with our brand and product.

c. Some posts with and about us around the web (Inc 5000, Estate Innovation, Geek Estate Blog, Business Wire, Innovate State)


1. Meet us and learn about Obie
You'll first talk to a member of the People Ops team on a 30 minute call; you won't need to prepare anything in advance. The goal of this conversation is to get to know you and mutually explore if we might be a good fit for each other. You'll learn more about Obie and have a chance to ask any questions about our company, team, culture, and product.

2. Meet the hiring manager
You'll get to have a 45 minute video interview with, Adam, the hiring manager. This discussion will be more technical in nature to ensure you have the skills needed to be successful in the role.

3. 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 project management strategies. More on this when you get there!

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:
Founded in 2017, Obie is paving a new path in insurance for landlords and real estate investors. Obie’s goal is to fundamentally change how insurance is bought and sold  by building technology and insurance products that increase ease and accessibility for the 17 million residential real estate investors and landlords in the US. Obie offers a superior insurance experience, allowing real estate investors and landlords to obtain the right coverage where it’s most convenient for them, whether that means using our digital quote tools, working with independent agents, or finding us through our integrations with industry partners.

With over 6,000 active policy holders, and over $20 billion in coverage secured, Obie has still barely scratched the surface of its growth potential. That growth is supported by $39 million secured in funding, positioning it perfectly to continue revolutionizing the industry.

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

Product & Engineering

Remote (United States)

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