At Obie, we don’t just insure properties — we ensure progress. With advanced technology, real-time data, and a vast network of agents and partners, we help real estate investors and landlords get insurance coverage whenever and wherever they need it. Thousands of owners nationwide trust us to be the insurance experts, so they don’t have to be.

Joining our team means embracing a fast-moving environment driven by innovation, collaboration, and constant progress. We learn quickly, iterate often, and celebrate wins together. If you're passionate about driving change and eager to impact the real estate and insurance market, Obie is the place for you.

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

While Obie does offer fully remote opportunities for those outside of Chicagoland, we are only currently hiring in the following states: AZ, DC, FL, GA, IL, IN, LA, MA, MI, MO, NH, NJ, NY, NC, OH, OR, PA, SC, SD, TN, TX, UT, WI

Brief Summary of Role

As an Agency Sales Manager at Obie, you are responsible for driving new agent appointments, sales strategies and account management on a national level. You’ll be expected to develop sales plans, analyze data and identify growth opportunities. You will also play a crucial role in recruiting and onboarding new partners to help fuel Obie’s growth in the independent agent channel!

What you'll Do

• Manage a portfolio of agency accounts, ensuring their satisfaction, retention and growth
• Build and maintain strong relationships with agency partners and serve as primary point of contact for all agency-related matters
• Analyze agency performance metrics such as sales volume and retention - identify trends, patterns and opportunities for improvement and provide guidance to help the agencies meet their goals
• Provide data-driven insights and recommendations to enhance the agency experience
• Maintain up-to-date knowledge of Obie’s products, services and underwriting guidelines
• Identify and recruit new agency partners that align with Obie’s target market and growth objectives; oversee the intake process for new agencies, ensuring they have everything they need to write business with Obie
• Manage and cultivate relationships with key national accounts, negotiating terms, and ensuring their satisfaction; develop strategic account plans to drive growth and expand opportunities

What you'll Bring

• 3+ years of experience working in an agency or with agency partners
• Previous experience working with agency partners, brokerages, or agency networks is highly desirable
• Excellent relationship building and networking skills to establish strong partnerships with agency partners
• In-depth knowledge of sales strategies, techniques, and best practices
• Strong strategic mindset with the ability to develop and execute sales strategies at a national level
• Strong oral and written communication skills with the ability to manage remote or in-person audiences
• Passion for early-stage startups and/or high growth environments
• Able to deal well with ambiguity and maintain composure in complex situations
• Active Property and Casualty license required

Interview Process

At Obie, transparency is core to our interview process. We focus on open communication and a positive experience; no trick questions—just honest conversations about your skills and aspirations. To help you prepare, please familiarize yourself with these resources before moving forward:

• Our company’s blog to learn more about the market we serve and the information our customers value.
• Check out our LinkedIn to see how people interact with our brand and product.
• Press and podcast features like Inc. 5000, TechCrunch, Innovate State, Uncontested Investing Podcast, Insurtech Amplified Podcast

1. Meet us and get to know Obie
   You'll first talk to Kara on a 30-minute call to determine whether we’re a good fit for one another. You’ll learn more about Obie and have the chance to ask about our company, team, culture, and product.
2. Meet the hiring manager
   Next, you'll have a 45-minute video interview with the hiring manager, Matt Lossmann, to assess your technical skills for the role.
3. Complete a Project Exercise
   This role requires strong strategic planning, relationship building, and communication 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. 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

Moving Forward with Obie

Obie is leading the future of real estate investment protection, securing over $25 billion in coverage for thousands of policyholders nationwide. Backed by $39 million in funding and recognized as a top workplace by Built In and Inc., we’re committed to driving progress for our customers and team. Through advanced digital tools, a trusted agent network, and strategic partnerships, Obie provides real estate investors the insurance coverage they need to move forward confidently.

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

Obie values transparency and data driven decision making, enabling us to have a consistent and equitable approach to compensation. We are informed by a benchmarking tool which provides real time compensation data allowing us to regularly check our salary ranges against other venture backed companies and startups within our industry. We've provided the full base salary range for this role below, but please note that we typically target the mid point of the salary range to allow room for growth within the role. Your salary is dependent upon many factors, including years of relevant experience, expertise, etc.

During your first interview, you can expect to have an open conversation with your recruiter regarding your compensation expectations.