Obie Insurance is not just transforming the landlord insurance industry, it’s redefining what it means to be a great place to work. With a remote-first culture grounded in transparency, flexibility, and personal growth, Obie creates an environment where employees can thrive professionally and personally. From streamlining insurance for landlords across all 50 states to building a team-oriented, values-driven workplace, Obie exemplifies innovation both in product and people. What truly sets Obie apart is its unwavering commitment to employee well-being. The company offers a $100/month fitness stipend and sponsors activities like yoga and fitness challenges through its wellness and fun committees. Employees benefit from Flexible Time Off (FTO) with no maximum cap, and are encouraged to take the time they need. Obie also provides 12 weeks of paid parental leave, pet insurance, and flexible hours. Professional growth is baked into the culture with a $1,000 annual learning and development stipend, monthly “Lunch and Learns” that help new hires connect, and open “Ask Me Anything” forums with leadership that reinforce the company’s transparent ethos. Obie’s core values, aren’t just buzzwords. They’re lived daily through virtual coffee chats, Slack-based interest groups, employee-led events, and a genuine encouragement of feedback and innovation. Obie’s leadership knows that happy, empowered employees build great products and even better teams. With industry recognition, Obie is proud to be a company where employees feel seen, supported, and motivated to grow.
