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

The Program Manager thrives when taking on complex operational challenges and breaking them apart into bite sized executional workstreams. An individual successful in this role works well cross-functionally, is driven by the goal of aligning stakeholders around a shared vision, and has a bias to action for execution. 

The individual in this role will bring proven project management skills in fast-scaling startup environments as well as strong business judgment with an ability to think creatively.

What you'll Do

• Lead program teams to execute enterprise wide initiatives while demonstrating sound judgment, critical thinking skills, and a sense of urgency
• Create, revise and maintain program and resource plans (including defining scope, deliverables, and ROI for each program)
• Complete standard program communications such as status updates, risk mitigation, and implementation plans
• Establish and maintain a strong partnership with internal stakeholders & involve the right stakeholders needed to resolve blockers quickly
• Proactively highlight cross-functional gaps and identify strategic initiatives to execute
• Execute on improvements to program management process and organizational efficiency

What you'll Bring

• 3 years+ consulting and/or program management in a scaling startup environment
• Demonstrated ability to maintain poise and a positive attitude in a challenging, fast-paced, and dynamic environment
• Skilled in process mapping, analysis of as-is and to-be processes, and gap assessments
• Ability to work with limited direction and with ambiguity without a loss of performance
• Excellent written and oral communication skills
• Experience interacting with technical and functional teams
• Experience and comfort presenting to Senior Management
• Demonstrated excellence in influencing and managing change across a distributed team
• Possesses a passion for process improvement with an approach that encourages innovation, elimination of waste, and efficiency improvements
• Demonstrated ability to understand and explain complex business processes, systems, and tools with a specific focus on upstream/downstream impact
• Ability to facilitate brainstorming sessions to gather requirements

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 Skylar 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, Denise Pickering, 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 present you with a short exercise to complete to provide you a chance to flex those muscles. You’ll 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 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 your recruiter regarding your compensation expectations.