Direct Customer Success Representative

Direct Customer Success Representative

What You’ll Do:

As a Direct Customer Success Representative, you’ll support both our internal Direct Sales team and our agency partners by delivering exceptional service to our insureds. This hybrid role combines traditional customer service responsibilities with those of a licensed account manager, offering a unique opportunity to directly consult clients on their insurance needs while managing a wide range of support tasks.

• Serve as the first point of contact for inbound calls, emails, and chat messages from direct clients, Inside Insurance Agents, and agency partners.
  
  
• Build strong, professional relationships by providing prompt, empathetic, and solutions-oriented support.
  
  
• Support our Direct Sales Representatives by addressing service needs and ensuring a smooth post-sale experience.
  
  
• Process policy servicing requests such as endorsements, change requests, and certificates of insurance.
  
  
• Advise insureds on available coverage options and help them understand how to best protect their properties.
  
  
• Resolve customer and billing-related inquiries accurately and efficiently.
  
  
• Maintain accurate and complete account notes in our CRM (e.g., HubSpot or Salesforce).
  
  
• Partner with Product teams by escalating customer feedback and sharing product insights.
  
  
• Guide customers and agents on best practices for using our digital tools and platforms.
  
  
• Assist with additional tasks and projects as needed.

Basic Requirements:

• Active Property & Casualty license (required).
  
  
• 3+ years of experience in a similar servicing or account management role.
  
  
• Commercial real estate insurance experience (preferred).
  
  
• Strong problem-solving and multitasking skills, with the ability to manage shifting priorities.
  
  
• Comfort using CRM systems, telephony tools, and cloud-based platforms.
  
  
• Adaptability to evolving processes and technology.
  
  
• Excellent written and verbal communication skills, with the ability to de-escalate and build rapport.
  
  
• Successful completion of assessments, knowledge checks, and training application exercises.
  
  
• Hybrid availability: Must be able to work from our downtown Chicago office three days per week (Tuesday through Thursday).

Benefits

• Base Salary: $57,500
• Health / Dental / Vision Benefits
• Employee Options Grant 
• 401K  
• Flexible Paid Time Off
• Paid National Holidays