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Director of Sales - Employee Benefits

Cottingham & Butler/ SISCO

1 Positions

ID: SnY3bTd6VU1KTnROcU5x

Posted On 03/22/2024

Job Overview

Position Summary:

Primarily responsible for achieving new business growth by successfully recruiting, developing, supporting, and managing performance of the sales team, alongside the VP of Sales.

Essential Functions:

  • Meet and exceed goals for new business production, retention and growth of programs.
  • Responsible for the recruitment, onboarding, retention, coaching, and development of staff. This includes career fairs, class speaking, regular 1-on-1 coaching, weekly team meetings, contributing to educational forums, building content and training programs, organizing the team, etc.
  • Be a spiritual leader of Benefit sales, with strong relationships across the entire sales team.
  • Travel on new and renewal meetings with sales executives.
  • Measure, monitor, and motivate sales staff through activity tracking and performance coaching.
  • Oversee the annual performance review process for direct reports.
  • Develop a close working relationship with the new business analyst team to drive consistent conversion process to close new business.
  • Work with service leaders to ensure we are providing proper service to our clients.
  • Get personally involved in helping Sales Executives acquire, maintain and retain significant accounts
  • Drive the implementation and improvement of a sales training and development program.
  • Refine the Benefit’s value proposition to develop a clear plan for how we win business and ensure that this is trained and that we actually implement the plan.
  • Create an annual client marketing strategy with tactics and plans to build our presence in the marketplace and help our sales executives get in front of more prospects. This includes optimizes the use of marketing tools like our CRM (Salesforce) and other technology tools (ZoomInfo).
  • Work closely with the Benefit’s leaders to provide clear career paths for sales executives to move up to larger clients and/or management.
  • Identify and address major strategic issues related to sales, including a) defining territories, b) refining producer compensation, c) setting uniform performance standards d) development of a sales training program e) use of the 80/20 principle to reduce complexity in the business, f) CRM compliance.

Key Performance Metrics

  • New business production versus goal
  • New business production rate per sales executive
  • Producer sales metrics: activity, meetings, conversion rates, etc.
  • Client retention rate
  • Growth of sales staff as measured by total sales executives and number of validated sales executives
  • Producer turnover & Engage360 management scoring
  • Average account size of unvalidated and validated producers

Other Functions:

  • Other duties as assigned by Supervisor.


  • Bachelor’s Degree or equivalent experience.


  • Business-to-Business sales experience preferred
  • People Management or Leadership experience preferred
  • A successful track record of achieving results
  • No industry experience required

Specific Skills:

  • Excellent verbal and written communication skills.
  • Ability to set deadlines, follow through and work under pressure.
  • Ability to differentiate and prioritize tasks. A great time manager.
  • Computer proficiency in Word and Excel.
  • Ability to work as a team member.
  • Superior organizational, analytical, and negotiation skills.
  • Ability to delegate tasks as appropriate.
  • Personal presence to interact professionally both internally and externally.
  • Ability to influence, coach, and mentor associates.
  • Detailed knowledge of business-to-business sales process.
  • Excellent leadership skills, high emotional intelligence, curious, and driven to help others succeed.
  • A desire to become a student of the game and expert in the Employee Benefits field.
  • Confidence in oneself

Specialized Knowledge, Licenses, etc.:

  • Must get licensed in Life & Health Insurance with first 3 months of employment

Supervisory Responsibility:

  • Sales Executives, Sales Interns

Office and Travel Expectations:

  • This is an onsite position available in Dubuque or Madison offices
  • Expectations to be in office over 80% of the time unless traveling
  • Ability to travel outside 8-5 hours when necessary for job (not common, but sometimes needed).

Primary Contact


Human Resources












Job Details




Dubuque, IA

Job Type



Full Time

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About the Company


Cottingham & Butler is one of the largest insurance brokers in the U.S. with over 1,200 employees dedicated to providing our clients with advice and insurance products to manage the risks they face. Better Every Day. That's our promise to our employees and our clients. We deliver better advice, better service, and better ideas than our competitors. Every Day. It's a commitment to challenging conventional wisdom, innovating, improving how we serve our clients and growing as industry professionals. This approach has produced superior results for our clients, endless opportunities for our employees, and a growth track record that continues to outperform the industry.