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
Click here for some insight into our culture!
The Baldwin Group will not accept unsolicited resumes from any source other than directly from a candidate who applies on our career site. Any unsolicited resumes sent to The Baldwin Group, including unsolicited resumes sent via any source from an Agency, will not be considered and are not subject to any fees for any placement resulting from the receipt of an unsolicited resume.
Skills Required
- 3-5 years of experience in business development, outbound sales, or channel partnerships
- Proven track record of hitting or exceeding outbound activity targets
- Comfort making cold calls and sending cold emails everyday
- Strong discovery and qualification skills
- CRM fluency (Salesforce preferred)
- Excellent communication skills
The Baldwin Group Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about The Baldwin Group and has not been reviewed or approved by The Baldwin Group.
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Healthcare Strength — Health coverage includes flexible medical options, 24/7 telemedicine, mental health support, company‑paid life and disability, plus dental and vision. Feedback suggests these comprehensive offerings contribute meaningfully to total rewards.
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Leave & Time Off Breadth — Time‑off programs span parental leave, paid holidays, paid sick days, and flexible PTO, with some teams citing unlimited PTO. Feedback suggests flexible PTO depth is a valued element of the package.
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Equity Value & Accessibility — Equity grants are provided to all new hires. Feedback suggests broad‑based equity can enhance perceived fairness and long‑term value.
The Baldwin Group Insights
What We Do
BRP is now The Baldwin Group! We’ve updated our name to reflect our unified group of talented teams across the country. The Baldwin Group is a cohesive group of experts in business insurance, employee benefits, retirement planning, and all areas of private and personal insurance. Since our founding in 2011, we’ve evolved from a local business into a national firm with a vast network of specializations and industry practices for the benefit of our more than two million clients across the country. In addition, we have built excellent relationships with a wide range of insurance company partners. These relationships, coupled with our entrepreneurial and family-oriented culture, and deep expertise enable us to seamlessly deliver a breadth of innovative solutions to clients. At The Baldwin Group, we help provide the solutions our clients need to have confidence and gain peace of mind as they pursue what’s possible for themselves, their families, and their businesses. Whether they are renting their first apartment or buying a larger home, opening a small business or taking their company public, we offer solutions to support them on every step of their journey. This has been our story since the beginning—we provide the indispensable expertise and quality insights that give our clients peace of mind to pursue their purpose, passion, and dreams. And that’s what The Baldwin Group will continue to do for years to come: we Protect the Possible℠.
