People Ops Generalist

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

The People Ops team enables Obie’s success by designing and implementing innovative people programs that attract and enable the Obie team to do their best work. As a People Ops Generalist, you’ll work to ensure we deliver and execute best in class programs across the full employee lifecycle - this includes initiatives involving attracting, hiring, engaging, retaining and developing the staff at Obie.  

This is an excellent opportunity for someone interested in gaining exposure across the full spectrum of people operations at a scaling startup.  This is a hybrid role with the individual having availability to be in our Chicago office 2 times per week.

What you'll Do

• Collaboratively work with the People Ops team to find ways to continuously improve, enhance, or add to the employee experience with our people processes
• Execute day-to-day people processes, including but not limited to onboarding, offboarding, HRIS management, performance management, internal transfers, and more
• Support strategic planning for people-related programs (e.g., employee engagement, individual contributor to manager process, people plans & metrics, organizational changes)
• Cultivate a positive recruiting experience for candidates on job requisitions you’re assigned
• Gather feedback and find ways to automate and better leverage our technology platforms
• Handle employment-related inquiries from applicants, employees, and managers, escalating complex and/or sensitive matters
• Gather and analyze People Ops metrics, drawing meaningful insights and proposing actions to address trends
• Support managers with employee relations, systems implementation, performance management, People Ops policies, and other related topics
• Assist with the administration of health and wellness benefits, company perks and maintain employee enrollment data
• Support culture programs to ensure the team is facilitating initiatives to create the type of culture the overall organization desires and thrives 
• Complete other duties as assigned

What you'll Bring

• 3+ years working in HR or People Operations
• Results-oriented with a high attention to detail
• Quick learner and ability to grasp new concepts quickly and apply learned concepts to future work
• Bias for action with a hands-on-get-stuff-done mentality
• Demonstrated ability to work within and be successful in a high-growth environment, adapting and adjusting quickly to changing priorities 
• Excellent Google Suite skills: Sheets, Docs, Slides, Forms
• Excellent communication skills; the ability to translate data for different audiences
• The ability to build and maintain successful relationships with all levels of the organization by achieving credibility and influencing key decisions 
• Demonstrated discretion and sound judgment handling sensitive and confidential data
• Demonstrated project management skills and ability to execute on projects independently and resourcefully

Nice to Haves

• Experience in remote and distributed companies
• Experience in the tech industry and at a startup 
• Familiarity with Rippling and Slack

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 a