New Business Supervisor: Hybrid Remote and In-Office Chicago, IL



We’re actively looking for amazing people like you to join our team!


Hybrid Work Arrangement

Work Environment:

Modern office with standing desks + a café fully stocked with coffee, teas, purified water, and snacks.



This position supervises a team of employees and works closely with them and clients directly to provide a high level of customer service for new business reviews and installations for the Flex GA group and individual products. Provides ongoing support, training, implements policies and procedures, performance metrics, coaching and performance reviews for the team on a regular basis.  Works closely with each team member to identify opportunities for performance improvement and provides recognition for improved or exceptional performance.  Works closely with the Manager to address issues related to the team.  Stays positive and focused at all times and works with the team to maintain a positive spirit.  This position is hands-on and will perform new business implementations as well as post implementation audits and resolves any outstanding issues. 


Key Responsibilities:

Supervises staff of New Business Team

  • Delegates new business assignments to team for GA product sales.
  • Performance Assessments
    • Completes semi-annual and annual performance reviews.
    • Provides ongoing feedback via multiple channels of metric tracking and performance which could include but are not limited to call and email review, service training skills, incentives, and more.
    • Provides discipline and terminations as required.
  • Encourages service development through training, driving utilization of available resources, and service evaluations to improve and maintain customer relationships.
  • Provides training and cross training on all aspects of the position for existing or new team members to develop and maintain efficiency
  • Determines work procedures, oversees work assignments, and expedites workflows.
  • Performs Interviewing and hiring of new team members
  • Provides encouragement and positivity to promote a self-motivated and stimulating working environment
  • Provides weekly and monthly individual reports including production and quality for all carriers and internal responsibilities; reviews team performance regularly to ensure performance and production goals are being met. 


Customer Serivce: Leads by example to ensure that the New Business team provides exceptional customer service to brokers and internal sales staff.   In addition to supervisory responsibilities will be responsible for the installation of new policies.

  • Supports team with system or service escalations and completes or aids with  group installations and policy installations as needed.
  • Keeps management and all internal teams up to date on the status of new business processing.
  • Builds strong relationships with carrier partners and keeps up to date on all carrier rules, policies and procedures.  Training the team as necessary
  • Develops and recommends policies and procedures to support business needs and improve team performance.   
  • Provides back-up as needed for the Customer Service team.
  • Handles carrier escalations and exceptions as needed for all lines of coverage. 
  • Ability to meet with and train external contacts to support business needs, including brokers. 


Installations: Supervises and performs all aspects of new business implementation for all GA products. Ensures that available communications are utilized as intended and Dynamics workflows and audit reports are completed to ensure accuracy. Works with management throughout the year to manage installations from beginning to end. Works with team to ensure installation issues are resolved within required timelines. Works closely with Service and Account Management on the Bentegro new case submissions.  Identifies opportunities to improve policies and procedures. 

Regular duties include:

  • Thoroughly reviews and reconciles group health applications in preparation for submission to carrier underwriting..  Verifies participation, collects applications or waivers for all eligible individuals and ensures that employer-level documents are satisfactorily completed. 
  • Obtains prescreen quotes for employer group applicants.  Ensures that the prescreen request contains correct census information as well as a complete and detailed medical history.
  • Reviews individual medical and Medicare applications for completeness and accuracy.  Ensures that all required documents are completed and that the applications are submitted within the proper enrollment periods.
  • Requests any additional items needed to fulfill underwriting requirements for group, individual and Medicare applications and follows up on outstanding items in a timely manner.
  • Submits group and individual applications to underwriting and closely monitors their progress.  Conducts regular status checks until a final underwriting decision has been made.  Updates Dynamics  with final policy information including the underwriting decision, application effective date and policy number, plan name and premium rates. 
  • Provides exceptional service and maintains highly effective relationships with Flex Sales Representatives, brokers and their staff.  Researches and responds to brokers’ questions.  Responds to phone calls and emails from brokers and carriers promptly.
  • Cultivates strong working relationships with insurance carrier representatives.
  • Records group, individual, Medicare, and prescreen applications received each day and assigns them to new business team members for processing.  Assigns time sensitive applications promptly.
  • Monitors current case load for each team member to ensure that work load is distributed evenly.
  • Coordinates monthly status check assignments for individual policy audits.
  • Creates team schedules for routine tasks such as direct application entry.


Testing Support: Participates with IT and management in the implementation and testing of software changes to Dynamics,or other systems within the GA departments as needed.


Documentation: Involved in the development of department procedural documentation for existing procedures and the new processes for New Business Installations.

Stays up-to-date with our technology solutions as well as new and existing products.

Strategizes with management and implementation team to promote product growth and development.  Provides support to CDHP with New Business and Renewals as needed.

Works closely with Manager on any issues impacting the team.

Assists in the ongoing updating of data within CRM system.


We are a dynamic company in a rapidly changing environment.  Accordingly, the responsibilities associated with this position will change in accordance with the company’s business needs.  More specifically, the incumbent may be required to perform additional and/or different responsibilities from those set forth above.




  • High School degree with additional specialized training in related industry and database.
  • Bachelor's degree in Business Administration or related preferred.



  • Strong proficiency with Microsoft applications and database software; especially Outlook, Word, intermediate Excel and PowerPoint
  • Minimum of 3 years experience in a related new business implementation insurance role with high volume phone and email communications.
  • Minimum of 2 years experience in a lead or supervisory position with related duties.
  • Familiarity with navigating and explaining database applications
  • Thorough working knowledge (at least 2 years) of health-related employee benefits including Health and Ancillary coverage’s along with a general understanding of group health insurance benefits.  


Performance Skills:

  • Excellent communication skills, both written and verbal using good spelling, ability to present to various audiences.
  • Ability to delegate effectively and take initiative to maintain a positive work environment.  
  • Flexible and adaptable to change.  
  • Strong motivational and team building skills.  
  • Expertise in multi-tasking, organizing and prioritizing
  • Strong attention to detail
  • Ability to master tasks and identify ways to streamline processes and procedures to continually improve efficiencies
  • Demonstrates a high level of integrity and professionalism in handling confidential data
  • Able to perform well in a team environment and have exceptional people skills
  • Demonstrated proficiency with understanding and navigating database applications
  • Ability to set performance goals and expectations to ensure successful onboarding of new clients.  
  • Demonstrates the ability to resolve situations autonomously and provide support to team members in escalated situations
  • Excellent telephone etiquette and strong written & verbal communication skills
  • Proven ability to build relationships with brokers and clients; must be service oriented 
  • Ability to perform at highest level of accuracy while meeting established quotas and time frames
  • Excellent organization and time management skills to meet department deadlines
  • Demonstrated ability to learn quickly, master tasks, and train others
  • Professional demeanor and good presentation skills


Physical Requirements:

  • Given the seasonal nature of the business, incumbent will have limited ability to take vacation or personal days from November 1st through February 1st.
  • Some local travel may be required to visit producers, attend seminars, symposiums, or industry trade shows.



  • Ability to work successfully in a fast-paced, evolving environment while maintaining a high level of quality and professional courteous service.  
  • Ability to handle and delegate large volumes while maintaining high levels of quality and service.


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