At Obie, we are shaking up landlord insurance, making it easily available for landlords and real estate investors both when and where they need it. With a focus on driving efficiency and innovation for our customers and within our team, we’re on the search for new talent that can take Obie to the next level.

At Obie, you’ll collaborate with a diverse team that embraces evidence-based decision making, learns from failure, accepts feedback, and is always prepared to make changes for the better. You’ll be expected to operate with flexibility and leverage your curiosity to drive innovation while collaborating with colleagues across teams and areas of expertise. Our ideal teammates are kind, passionate, committed to excellence and eager to nerd out over the best ways to make Obie even better.

Our Chicago based employees are hybrid, and expected to be in office on Tuesdays and Thursdays.

Brief Summary of Role

We are seeking a proven insurance product leader to join our growing insurance operations team that is focused on developing, executing, and optimizing strategic plans and profitable growth in new and existing markets.

Those successful in this role will have broad property insurance expertise including countrywide P&L management as well as experience overseeing digital and manual underwriting solutions, operational and regulatory requirements, CAT management, process optimization, and building and launching new products and distribution channels. You have a demonstrated passion and creativity for solving complex market challenges to meet the needs of customers, partners, agents, and carriers.

In this role, you will be responsible for enhancing and evolving the overall insurance product, pricing, carrier, and distribution strategies and contribute to the prioritization of work efforts to maximize profitable growth and scale efficiently. You’ll be self-motivated and self-directed with a passion for collaborating. As with any startup environment, the ability to adjust and change direction with ease is critical.

What You'll Do:

Design and execute a wide breadth of insurance product management including pricing, forms, underwriting, compliance, go to market preparation, data insights, and operational process creation and refinement to ensure profitable growth
Develop and implement product strategies to achieve P&L goals: product development, marketing and retention programs, risk selection, segmentation, underwriting strategy, competitive analysis, and cost containment
Obtain and maintain capacity and programs with a variety of providers
Assist with identifying and deploying data enrichment solutions in a digital underwriting environment
Use your expertise to lead a team of insurance product managers to provide solutions that maximize growth and profitability across distribution channels
Develop, maintain, and monitor standard operating procedures to ensure compliance, promote efficiencies, and satisfy customers and distribution partners
Partner closely with Technology Product and Engineering teams to articulate, develop, and validate core system features and enhancements
Work closely with Claims TPA to ensure appropriate information is captured and communicated in order to address loss performance on current and future policies
Direct and manage data and analytics resources to maximize return on efforts for Obie
Provide thought leadership and guidance to influence priorities at Obie

What You'll Bring:

10+ years in product management, data analytics, or portfolio underwriting roles; some experience at an MGA/MGU/Program Administrator and/or insurtech preferred
5+ years experience as a leader of leaders
Existing relationships with capacity providers and fronting carriers
Proven success in developing, leading, and overseeing profitable product P&Ls
Expertise in product development and management, actuarial, underwriting, compliance, loss mitigation, CAT management, data insights, and policy operations’ best practices
Proven success at helping develop core systems and processes; including research, requirements, operations, deployment, and management
Ability to conduct quantitative and qualitative analysis to evaluate performance across various segments including proficiency with data analysis and visualization tools
Outstanding project management and time management skills with a proven ability to maintain composure and flexibility in a fast paced environment
Ability to adapt and remain flexible as business strategies are adjusted and refined
Clear and strong communicator with high proficiency for cross-functional collaboration
Exceptional written and verbal communication skills, as well as proven ability to foster and encourage teamwork and productive working relationships with stakeholders at all levels and across organizational lines
Enthusiastic to be an Obie brand representative and insurance industry authority to external parties

Interview Process

1. Meet us and learn about Obie

You'll first talk to a member of the people ops team on a 30 minute call; you won't need to prepare anything in advance. The goal of this conversation is to get to know you and mutually explore if we might be a good fit for each other. You'll learn more about Obie and have a chance to ask any questions about our company, team, culture, and product.

2. Meet the hiring manager

You'll get to have a 45 minute video interview with the hiring manager, Laura Olson. This discussion will be more technical in nature to ensure you have the skills needed to be successful in the role.

3. Project exercise

This role requires strong insurance product development and management skills, so we'll also present you with a short exercise to complete to provide you a chance to flex those muscles. You will be able to 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, 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.

More About Obie

Founded in 2017, Obie is paving a new path in insurance for landlords and real estate investors. Obie’s goal is to fundamentally change how insurance is bought and sold by building technology and insurance products that increase ease and accessibility for the 17 million residential real estate investors and landlords in the US. Obie offers a superior insurance experience, allowing real estate investors and landlords to obtain the right coverage where it’s most convenient for them, whether that means using our digital quote tools, working with independent agents, or finding us through our integrations with industry partners.

With over 6,000 active policy holders, and over $20 billion in coverage secured, Obie has still barely scratched the surface of its growth potential. That growth is supported by $39 million secured in funding, positioning it perfectly to continue revolutionizing the industry.

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

Flexible time off with an encouraged minimum time away to support a healthy work-life balance

12 weeks of Paid Parental Leave

Great health, dental and vision coverage

Life Insurance

Flexible Spending & Health Savings Accounts

Stock Options

401k match

Pet Insurance Reimbursement

Health and wellness benefit

Equipment budget - everything you need to do your best work

Professional development support

Summer hours

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