obie wins inc.'s workplace of the year 2024

Obie Doubles Down on Employee Satisfaction, Earns 2024 Inc. Best Workplaces Spot

Jun 18, 2024

CHICAGO, IL. Jun 18, 2024  ​​Obie is proud to announce that it has been named to Inc. Magazine’s 2024 Best Workplaces – its second consecutive year being ranked among American companies that have excelled at creating exceptional workplaces.

Through a rigorous selection process, Inc. analyzes data from thousands of submissions, including employee surveys and benefit audits. This year, Inc. Magazine's Best Workplaces list recognized just 543 American companies. Obie stood out for its exceptional performance in areas like management effectiveness, employee development opportunities, and fostering a positive company culture – both virtually and in its Chicago office.

“Each year, Inc.’s Best Workplaces program recognizes the very best in terms of companies that have fostered a truly amazing culture,” says Inc. editor-in-chief Mike Hofman. “We use hard metrics and data as well as qualitative measures for judging to find the very best—and we’re proud that the program is highly selective.”

A Culture of Feedback, Recognition and Growth

Having just surpassed its 100th employee milestone, Obie is dedicated to company well-being that transcends a simple list of perks. By fostering a culture of open communication, continuous feedback, professional development, and recognition, Obie is empowering its employees to thrive.

Through various channels – from "kudos channels" to pulse surveys – employees feel empowered to share their perspectives on benefits, growth opportunities, and overall experience. Regular in-depth surveys keep Obie attuned to evolving needs, while post-meeting feedback ensures continuous improvement in collaboration. 

Learning and development stipends encourage employees to pursue career-enriching learning experiences aligned with their personal and professional goals. Flexible work arrangements, a comprehensive health and wellness program, generous parental leave policies, and unique offerings like pet insurance reimbursement all cater to diverse lifestyles and needs.

Obie fosters a spirit of camaraderie through the "Top Dog" program, which recognizes outstanding work through peer nominations. Internal challenges and company-wide events like the "Obie Olympics" add a fun and engaging element, while a robust benefits package emphasizes Obie's commitment to employee well-being.

“No one person is going to disrupt the entire insurance industry,” said Ryan Letzeiser, CEO and Co-founder of Obie. “It will take a team of bright, innovative employees to change the game. For us to win this award tells us that we are doing exactly what we need to foster a space where our employees feel valued, their voices heard, and their growth exponential. Enough so that we can build the future of insurance the right way.” 

Career Opportunities at Obie

We’re excited to add new talent to our growing team consistently. Our careers page offers more about Obie, our values, and current opportunities. Check that out here:

Don’t see a role that fits your skills or interests? Email with a description of what you’d like to bring to the team at Obie and attach your resume.

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 you are 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. Learn more at

About Inc. Media

The world’s most trusted business-media brand, Inc. offers entrepreneurs the knowledge, tools, connections, and community to build great companies. Its award-winning multiplatform content reaches more than 50 million people each month across a variety of channels including websites, newsletters, social media, podcasts, and print. For more information, visit

About Quantum Workplace

Quantum Workplace, based in Omaha, Nebraska, is an HR technology company that serves organizations through employee-engagement surveys, action-planning tools, exit surveys, peer-to-peer recognition, performance evaluations, goal tracking, and leadership assessment. For more information, visit