[Hiring] Customer Service Representative II @MSI, part of The Baldwin Group

Role Description

This is a hands-on service role for experienced, licensed insurance professionals who are comfortable handling property policies and customer requests independently. You’ll be part of a structured service team responsible for:

• Processing endorsements and policy changes
• Handling billing and renewal questions
• Communicating clearly with customers and carriers
• Maintaining accurate documentation in Salesforce

This role is ideal for someone who:

• Has solid insurance servicing experience
• Works well within defined processes
• Is comfortable managing a steady flow of cases and calls
• Takes pride in accuracy and responsiveness

You won’t be managing a book of business or responsible for sales quotas — this is a service-focused role where execution, consistency, and professionalism matter.

Qualifications

• 4+ years working in the insurance industry (homeowners/property experience strongly preferred)
• 2+ years in a customer-facing service role
• Active Property & Casualty insurance license (required before starting — non-negotiable)

Requirements

• Experience servicing HO3, DP3, or landlord policies
• Experience working in an MGA, agency, or carrier environment
• Strong understanding of endorsements and coverage structure
• Spanish fluency (preferred but not required)

Benefits

• Comprehensive health, dental, vision and life insurance
• Flexible paid time off including 12 week Paid Parental Leave
• Retirement savings plan with company match
• Equity participation opportunities
• Monthly stipends to support a healthy lifestyle and learning and development opportunities

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.

You'll first talk to Mary 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.

Complete a Project Exercise: This role requires strong verbal and written communication skills, so we’ll ask you to complete a short exercise. We’ll assess your problem-solving abilities, writing skills, empathy, demeanor, and organization skills. More details will come when you reach this step!

Meet the hiring manager: Next, you'll have a 45-minute video interview with the hiring managers, Ben Sax and Chrissy Palmer, to assess your technical skills for the role.

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.

Company Description

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.