Get more out of your search

Customize your job recommendations. Get email updates when new jobs open. Upload your resume and apply again quickly and easily.

Back to Search Results

Direct Sales Supervisor


The ideal Direct Sales Supervisor will have effective leadership skills and is able to provide direction and motivation to their staff to ensure Sentry continues to provide exceptional service on Sales calls.  This individual will lead our Dairyland team dedicated to Non-standard Auto and Motorcycle sales.  You will need availability Monday – Friday until 8 pm AZ time and one Saturday every seven.

What You'll Do

  • Coach, counsel, and motivate your sales service team
  • Develop and implement sales service standards
  • Improve sales service quality results by studying, evaluating and formulating ideas
  • Maintain knowledge of new or revised telecommunications systems
  • Provide work direction to your staff
  • Assist in the development of strategic objectives for the direct sales unit.
  • Implement policies and procedures
  • Provide expertise in handling sensitive/unusual sales service issues
  • Schedule staff accordingly and tracking performance
  • Assist with budget preparation and control operating expense

What it Takes

  • Associates Degree or equivalent work experience
  • 2-5+ years of previous work experience or knowledge of a sales service environment and previous supervisory experience
  • Ability to pass/maintain Property and Casualty Agent Licensing
  • Ability to provide leadership to employees within a fast-paced sales call center environment
  • Ability to prioritize work and maintain appropriate service standards
  • Ability to analyze data, identify trends, and communicate results
  • Working knowledge of telecommunication systems and call center software
  • Knowledge of insurance processes, procedures, and systems beneficial
  • Ability to respond to sensitive inquiries or complaints from customers, state insurance departments, producers, and others with tact and diplomacy
  • Knowledge of sales structure and internal workflow beneficial
  • Candidates must be available to work Saturdays

What You'll Receive

There is a reason why Sentry made Forbes’ list of America’s Best Midsize Employers in 2017, 2018, and 2019. At Sentry, we recognize there are many factors that contribute to your overall satisfaction both at work, and in your personal life. So, we provide a perfect mixture of compensation, benefits, company culture, and resources to ensure your everyday happiness. Below are some benefits that you’ll receive.

  • Competitive compensation to reward you for your hard work every day.
  • Generous Paid-Time Off Plan for you to enjoy time out of the office.
  • 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help fund your future. 
  • Group Medical, Dental, Vision and Life insurance to encourage a healthy lifestyle.
  • Pretax Dependent Care and Health Expense Reimbursement Accounts to ease taxes on health spending.
  • Extensive Work-Life Resources to lend a helping hand.
  • Volunteer Time Off so you can dedicate time to the community.
  • Sentry Foundation gift matching program to encourage charitable giving.

How You’ll Apply

If you are interested in joining Sentry’s team, select the one position that you are most interested in being considered for and complete your online application details. If you have applied with us before, you will only need to provide your email address and password. If this is your first time applying, you’ll need to create an account. Please complete your application and upload your resume online.

About Sentry

All of us at Sentry—more than 4,000 associates—have various talents, skills, and backgrounds. We work together to deliver on our promises to our policyholders every day. We’re proud to offer a full line of property, casualty, and life insurance products to help protect businesses, cars, homes, lives, and retirement income.


Our headquarters is in Stevens Point, Wisconsin, with claims and service offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.


Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we’re one of the largest and financially strongest mutual insurance companies in the United States. We’re rated A+ by A.M. Best, the industry's leading rating authority.


Get ready to own your future at Sentry. Opportunities await.

Equal Employment Opportunity

It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Irma Pastrana

Job Title:
Direct Sales Supervisor
Job ID:
Scottsdale, AZ
Full/Part Time:

Get more out of your search
  • See customized job recommendations
  • Get email updates when new jobs open
  • Save jobs to quickly find them later
  • Apply again quickly and easily