Director of People Operations

Chicago, IL /
Operations /
About Obie

Obie is reinventing the commercial insurance process. We offer property and casualty insurance specifically designed for landlords and real estate investors. Whether you're a seasoned investor or just starting out, Obie makes requesting a quote and getting coverage simple and transparent.

Obie is seeking a Director of People Operations to provide support to Obie team members and work with leadership to partner on performance, employee relations, human resource management, and strategic support for a wide range of people initiatives. You will function as a trusted business partner and are expected to maintain a high level of business literacy about Obie's key strategic plans, culture and its people.


    • Drive a culture of high performance, impact and champion key culture and values.
    • Oversee employee relations and work closely with management and employees to improve work relationships, build morale, increase productivity and impact.
    • Deliver insights and solutions to the management team to address business challenges and contribute to the development of successful business strategies.
    • Partner with leadership team to drive business growth and organizational effectiveness, lead change management initiatives, and build organizational capability.
    • Collaborate with management and finance on workforce planning and talent acquisition. 
    • Assist with recruitment efforts to help secure additional talent to join the team.
    • Directly support leadership with all people initiatives, including compensation, talent and performance.
    • Strengthen leadership and manager effectiveness, partnering with our L&D team to ensure managers are demonstrating our leadership competencies and modeling our values while developing and growing their employees.
    • Support the company’s culture and engagement goals through identification of issues, facilitation of planning solutions and reporting progress.
    • Ensure consistent interpretation of company policies and procedures, practices and principles relating to employee relations and risk management; counsel and advise management and recommend approaches to prevent and resolve problems.

Knowledge and Skills

    • BA/BS degree with 7+ years of experience working in Human Resources or a related function.
    • Experience in administering benefit plans (401k, health, transit) and HR operations that deliver a high quality experience for employees.
    • Experience assisting recruitment efforts is a plus.
    • Self-disciplined and solutions focused with experience excelling in a dynamic, fluid and fast-paced environment.
    • Previous experience working in a result driven or entrepreneurial environment required, technology company preferred.
    • Proven track record with creating solid relationships with internal business partners.
    • Passion for helping team leaders do their best to inspire their teams while retaining high performance and driving for results.
    • Knowledge of current labor laws, as well as recent changes and trends in employment practices.
    • Experience in a tech / insurance / insurtech / financial services industry is a plus.
    • Excellent written and verbal communication skills.
    • Superb judgement.
    • Ability to maintain strict confidentiality, establish trust and credibility and act with complete integrity.
    • Ability to identify and define issues, collect data, establish facts, and draw valid conclusions and develop recommendations and solutions that meet the needs of the company.
    • PHR or SPHR preferred.

What draws people to Obie

We are a venture-backed technology company. Our early success is due to the strength of our team. We recognize that our product is only as good as the people building and promoting it. We are a curious, creative, and analytical team, passionate about solving problems. Ask anyone who works here and you’ll hear similar reasons for why they joined:

Impact. By challenging the way it’s always been done, we solve problems that have a huge impact.
Autonomy. The opportunities to contribute and grow are limitless
Collaboration. We value rich discussion and multiple perspectives because we recognize it results in stronger outcomes.
People. We are inspired by the collection of smart, creative, and solutions-oriented people around us.

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:

Competitive salary
Unlimited vacation policy with a required minimum to support a healthy work-life balance
Equipment budget - everything you need to do your best work
Great healthcare, dental, and vision coverage
Stock options
Retirement plan
Group training and individual professional development support
Company off-sites to support team development (as COVID allows)
We will be testing a summer hours this year