Technical Project Manager

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.

Brief Summary of Role

As a Technical Project Manager (TPM), you’ll drive end-to-end delivery for some of Obie’s most important product and platform initiatives - with a particular emphasis on supporting our insurance product work as it expands (new lines of business, partner/business requests, and delivery across multiple engineering pods).

You’ll bring structure to ambiguity, translate goals into clear execution plans, and keep teams aligned as we ship in a fast-moving environment. You’ll coordinate scope, dependencies, risks, and release readiness while maintaining a high bar for quality - and you’ll be especially strong at protecting teams from scope creep by helping stakeholders make clear tradeoffs.

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.
  
• Scope and tradeoffs are your superpower: Proactively manage scope creep, clarify decisions, and help stakeholders make tradeoffs so teams can execute predictably.
  
• 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 bar: Partner with QA/Engineering/Product to define acceptance criteria, coordinate test planning, facilitate QA/business readiness reviews, and ensure release confidence (without being the primary “test case writer” or PR reviewer).
  
• 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.
  
• Demonstrated experience driving delivery with engineering teams (requirements -> execution -> release), including navigating ambiguity and competing priorities.
  
• Attention to detail for thorough quality assurance and product testing.
  
• Proven examples of managing scope creep and driving decisions/tradeoffs.
  
• Passionate about continuous improvement, learning, and sharing best practices; proactive with strong follow through.
  
• Proficiency with Atlassian suite.

Icing on the cake (nice to haves)

• Exposure to insurance / fintech / regulated domains (or adjacent complexity where business constraints matter)..
  
• Prior experience in product management or product-heavy TPM work (strong product intuition and domain ramp).
  
• Technical fluency (comfortable reading specs, API concepts, and system constraints)

When applying, be sure to include your favorite emoji (🫒🎊⛸️🦞) so we know that you’re a real human, who also loves emojis.

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 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.
2. 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.
3. 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!
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

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
• Retirement savings plan with company match

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 your recruiter regarding your compensation expectations.