Insurance and Risk Management for Landlords

Technical Project Manager

$75k - $110k
Job Type
3+ years
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About the role

About Obie

Obie is an insurance technology company, hyper-focused on driving value for the modern real estate investor and the partners they work with every day. Whether an owner, lender, agent, or property manager, Obie’s mission is to build technology and insurance products that drive efficiency and fundamentally change the way insurance is bought and sold.

As the industry leader in embedded and instant insurance products, Obie was recently honored as Business Insurance Best Places to Work and one of Inc Magazine's Fastest Growing Companies for 2022. Obie is one of a small number of companies that are both a Y-Combinator and NAR REACH accelerator alum. 

To date, Obie has raised $13.7 million from leading proptech investors including Battery Ventures, Thomvest Ventures, MetaProp, Second Century Ventures, and Funders Club. The company has two offices, one in Chicago, IL and the other in Sarasota, FL, but also offers employees the option to work remotely.

Obie is seeking a talented and experienced Technical Project Manager to help oversee initiatives that make Product at Obie more strategic and effective. The role sits within our growing Product team, and will be a liaison between various teams at Obie. As part of project ownership, you will focus on the larger business picture, understand relevant business requirements/goals and drive the team towards the right outcomes.

Applicant must be based in the US or Canada.

About the Job

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. People 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 and appropriate department stakeholders. You will identify, plan, and communicate project risks and roadblocks to the product management team.
  • You dream about spreadsheets and lookup tables: You will track progress on projects and provide regular updates to key stakeholders. Develop project plans that merge project requirements with company objectives and coordinate various managers and technical personnel during all project phases, from initial development through implementation.
  • Gantt charts excite you (and maybe even Jira): 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. 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 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.
  • Excellent analytical, organizational and project management skills.
  • Strong interpersonal and written/verbal communication skills are a must.
  • Ability to be flexible, adaptable and solutions-oriented in the face of problems.
  • Passion for trying, learning, improving, and sharing best practices.
  • Proactive team member with excellent attention to detail and follow through.
  • 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, Omni suite, Jira, 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 have: experience working on projects at scale and fast paced (preferably 50+ employees) in a Saas, Payments, or Insurtech environment.
  • Nice to have: 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, 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 (Commercial Observer, Estate Innovation, Geek Estate Blog, Business Wire))

d. Podcast appearances: (The Ryan Hanley Show, REM #22)

  1. Meet us and learn about Obie

You'll first talk to Kara, Rebecca, and/or Adam) 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.

  1. 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.

  1. Project exercise

This role requires strong planning, writing, 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 demeanour, and ability to leverage key product management strategies. More on this when you get there!

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

Equipment budget - everything you need to do your best work

Professional development support

Company off-sites to support team development (as COVID allows)

Summer hours

Why you should join Obie

Obie is the fastest, easiest, and most transparent way for landlords to get insurance!

Team Size:94
Location:Chicago, IL
Aaron Letzeiser
Aaron Letzeiser
Ryan Letzeiser
Ryan Letzeiser