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

The Director of Insurance Sales will bring extensive P&C insurance sales leadership experience and a proven track record of building scaled internal sales teams and programs with either a program administrator or carrier. The individual in this role will drive our overall strategy and thought leadership around insurance sales at Obie and will be responsible for leading and managing a team of sales professionals, driving revenue growth, developing clear and impactful processes and SOPs, and ensuring the achievement of sales goals and targets. The Director of Insurance Sales will also work closely with other departments to develop and implement effective sales strategies, improve partner and customer satisfaction, and build strong relationships with key accounts.

In this role, you’ll be a member of the insurance sales and growth team reporting directly to the CRO.

What You'll Do:

Develop and implement effective sales strategies to drive revenue growth and expand our market share, with a focus on optimizing operational efficiency and driving process enhancements across the team
Provide strong and credible leadership to a team of insurance sales professionals, setting a unified direction for the team and ensuring priorities are clear at all times
Implement a sales strategy and methodology to guide the sales team - provide guidance, coaching, and support to ensure the sales team meet and exceed their sales targets
Build strong relationships with key accounts and identify new business opportunities to increase sales and revenue
Work closely with other departments, including product, partnerships, marketing, underwriting, and operations to develop and implement effective sales strategies and improve customer satisfaction
Prepare and present regular sales reports and forecasts to senior management, highlighting key trends, opportunities, and risks
Keep up-to-date with industry trends, best practices, and emerging technologies to ensure the company remains competitive in the marketplace
Collaborate with other senior executives to develop and implement overall business strategy
Lead strategic planning for insurance sales, including setting OKRs, forecasting performance, tracking measurements and providing recommendations for increasing efficiency and success
Work cross functionally to drive insurance sales operations initiatives and support company OKRs
Create, document and ensure the efficient execution of sales processes across the insurance sales teams at Obie
Own Sales CRM and lead efforts to optimize the sales tech stack
Work closely with insurance sales team leads on strategic ideas and translate them into data supported initiatives
Ensure compliance with all regulatory requirements and company policies and procedures

What You'll Bring:

Bachelor's degree in Business, Marketing, or a related field
Minimum of 6 years of experience in insurance sales and/or operational leadership roles
Proven track record of achieving sales targets and driving revenue growth
Strong leadership and management skills, with the ability to motivate and develop a team of sales professionals
A strong understanding of the steps involved in a sales cycle and ability to leverage each stage to advance the sale is required
Excellent communication, negotiation, and presentation skills
Strong analytical and problem-solving skills
Ability to work independently, prioritize tasks, and manage multiple projects simultaneously
Deep knowledge of insurance industry regulations, policies, and procedures
Willingness to travel as required
Proficiency with Salesforce a plus

Interview Process

1. Meet us and learn about Obie

You'll first talk to a member of the people operations 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, Brad Auerbach. 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 a strong understanding of sales as well as operational skills so we'll 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 gauge your understanding of the sales cycle and key kpis, your ability to find operational efficiencies, along with your leadership and communication skills, empathy, and general demeanor. 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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