Jobs and Careers

Business Development Specialist

United StatesRemotefull_timeVerifiedPosted 5 May 2026

💰 $100,000/yr($60,000/yr – $100,000/yr)

About the role

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: