Customer Success Advocate

Bold Penguin is where technology meets the human touch in commercial insurance. With a heavy focus on agents, Bold Penguin upgrades the user experience for businesses, creates an easy tool for agents, and offers a streamlined process of underwriting for carriers. Founded by a group of entrepreneurs who spent their early days working with Allstate, Nationwide, Progressive, regional carriers and established insurance agencies.


As the primary pilot of our software product, the Customer Success Advocate is the focal point of where technology meets the human touch at Bold Penguin. The Customer Success Advocate is an expert for every business owner that comes through our platform. There are thousands of different kinds of businesses, all with different risks, and it is the core responsibility of this role to help each customer figure out how to categorize their business, guide them through our process, and then use our technology to connect them with the best agent possible for them.


  • Utilize our software to create the perfect match, every single time
  • Consistently deliver excellent customer service
  • Coachable attitude with a passion for learning
  • Adapt to new processes and technologies as they are developed and deployed
  • Ability to communicate and multitask effectively
  • Desire to contribute to a high energy, positive environment


  • Strong Phone Skills - Ability to control and carry a conversation
  • Comfortable working with CRM Tools, Google Apps, Microsoft Office
  • High School Diploma, Undergraduate Degree Preferred
  • Proactive Approach to Problem Solving
  • 2+ years of Customer Service or Contact Center Experience

Preferred, but not required

Experience in the Commercial Insurance Industry

Interpersonal Skills

Salary & Benefits

To learn more about Bold Penguin’s results-focused culture and employee-focused perks, read more on our careers page.

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