Business Development Specialist in Chicago, Illinois at Obie

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.

Brief Summary of Role

The Business Development Specialist will be responsible for identifying, pursuing, and closing new channel partnerships that expand Obie's distribution footprint. This is a hunter role — you own your pipeline from first contact to signed agreement, and you thrive in environments where no one hands you a list of leads.

What you'll Do

• Build and work your own pipeline from scratch — researching target partner segments, identifying decision-makers, and executing outbound sequences across phone, email, and LinkedIn daily
• Make a high volume of outbound calls and send personalized email sequences every week — this is not a passive relationship management role
• Prospect into real estate brokerages, PropTech platforms, property management companies, investor networks, and other distribution channels where landlords and real estate investors live
• Develop creative outreach strategies that cut through noise — you'll write your own copy, build your own sequences, and iterate based on what converts
• Run discovery calls and product presentations with prospective partners, building a compelling case for why Obie belongs in their ecosystem
• Negotiate and close partnership agreements, then transition activated partners to the account management team
• Track all activity, pipeline stages, and outcomes in Salesforce — you keep your own data clean and use it to sharpen your approach
• Collaborate with marketing, product, and leadership to develop outbound collateral, refine ICP targeting, and share field intelligence that makes the whole team smarter

What you'll Bring

• 3–5 years of experience in business development, outbound sales, or channel partnerships — ideally in a startup or high-growth environment where you built a pipeline yourself
• Proven track record of hitting or exceeding outbound activity targets (calls, emails, meetings booked)
• Comfort making cold calls and sending cold emails every single day — you see rejection as data, not defeat
• Creative prospecting instincts — you find angles others miss and write outreach that actually gets responses
• Strong discovery and qualification skills; you know how to run a call that moves a deal forward
• CRM fluency (Salesforce preferred); you document everything and trust your pipeline data
• Excellent communication skills — clear, direct, and able to explain insurance concepts without putting people to sleep
• Passion for early-stage environments where the playbook is still being written

Nice to Haves

• Experience in InsurTech, PropTech, or real estate-adjacent industries
• Chicago-based or able to come into the Chicago office as needed

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 to assess your technical skills for the role.
3. Complete a Project Exercise
   This role requires strong prospecting and communication skills, so we’ll ask you to complete a short exercise to flex those muscles. More details will come when you reach this step!
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:

• Comprehensive health, dental, vision and life insurance
• Flexible paid time off
• Retirement savings plan with company match

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.