Business Development Specialist

The Baldwin Group

1d • Hybrid

About The Position

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.

Requirements

• 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

Responsibilities

• 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 This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed