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Region Manager

We are seeking a self-motivated sales leader to guide a team of premier sales professionals as a Region Manager within the Direct Writer segment of Sentry. This team provides Commercial Lines of Insurance, 401(k), and Life Insurance needed in today’s world to safeguard the businesses across the North Region. As the Region Manager, you will develop and implement a strategic and tactical plan that focuses on development of your team, including recruiting, performance management, sales, customer acquisition, customer retention and financial goals.

This is your chance to combine a rewarding career filled with success in our North Region including: Minnesota, North Dakota, South Dakota, and Nebraska. Residency within the territory is required. 

What You’ll Do

As a Region Manager, you’ll hire and develop a team of Account Executives who will sell our Sentry products including commercial insurance, 401(k), and life insurance in Sentry’s 9 Focused Markets. 

In addition, you’ll:

  • Assist your team with software programs and systems used in our sales process

  • Encourage, train and work with each of your team members to develop their book of business and maximize selling opportunities

  • Recruit and train your team, while providing leadership and encouraging high morale within your region

  • Monitor, review and evaluate your team’s development

  • Manage expenses within your territory

  • Maintain state licensing and participate in outside studies to improve sales skills

  • Prepare reports relating to production, loss ratios, etc.

What it Takes

  • Bachelor’s degree or equivalent work experience

  • 2+ years of related work experience

  • Exceptional sales, communication and relationship building skills

  • A self-disciplined individual that can thrive in a remote work environment

  • Ability to multi-task, prioritize, communicate effectively and remain organized

  • Strong analytical and math skills

  • Acceptable Motor Vehicle Record with a valid driver’s license and able to meet travel requirements

  • Required to have primary residence within your sales territory

Based on qualifications and experience, the base salary range is $88,900-$122,200 with additional earning potential including other incentives on new and renewal business.

What You’ll Receive

At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you’ll receive.

  • Company car with gas card

  • Comprehensive, ongoing training, including licensure

  • Laptop, cell phone reimbursement, home office setup, and more

  • 401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.

  • Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program.

  • Generous Paid-Time Off plan for you to enjoy time out of the office as well as Volunteer-Time Off.

  • Group Medical, Dental, Vision, Life Insurance, Parental Leave, and our Health and Wellness benefits to encourage a healthy lifestyle.

  • Well-being and Employee Assistance programs.

  • Sentry Foundation gift matching program to encourage charitable giving.

About Sentry

We take great pride in making Forbes’ list of America’s Best Midsize Employers. A lot of different factors go into that honor, many of which contribute to your job satisfaction.

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.

Our headquarters is in Stevens Point, Wisconsin, with 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.

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

Casey Van Der Geest

Casey.VanDerGeest@sentry.com 

Equal Employment Opportunity

Sentry is an Equal Opportunity Employer. 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.

Average salary estimate

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$88900K
$122200K

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What You Should Know About Region Manager, Sentry

If you're an ambitious sales professional looking to take your career to the next level, Sentry has an exciting opportunity for you as a Region Manager in Minneapolis, MN! In this role, you'll lead an elite team of sales experts dedicated to delivering top-notch Commercial Lines of Insurance, 401(k), and Life Insurance to businesses across the North Region, including Minnesota, North Dakota, South Dakota, and Nebraska. Your primary mission will be to craft and execute a strategic plan that prioritizes team development, customer acquisition, and solid financial outcomes. What's great about being a Region Manager at Sentry is that you have the chance to empower your team of Account Executives while fostering a motivating and high-energy environment. Not only will you recruit and train talent, but you’ll also guide them through the latest software used in our sales process, ensuring they have the tools at their disposal to flourish. You'll wear many hats—monitoring production, managing expenses, and keeping up with state licensing requirements, while all the while being a cheerleader for your team's growth. If you're self-disciplined, have stellar communication skills, and thrive in a remote work setting, we’d love to see you at Sentry. So, if you’re ready to take on a fulfilling role that comes with generous compensation, a supportive workplace environment, and a commitment to your professional growth, apply today and let’s create a successful future together!

Frequently Asked Questions (FAQs) for Region Manager Role at Sentry
What are the responsibilities of a Region Manager at Sentry?

As a Region Manager at Sentry, your key responsibilities include guiding a team of Account Executives in selling Commercial Lines of Insurance, 401(k), and Life Insurance. You'll develop a strategic and tactical plan for your team's growth, handle recruitment and training, monitor team performance, manage expenses, and maintain state licensing. It's a multifaceted role designed for someone who loves to lead and foster a high-energy environment while achieving financial goals.

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What qualifications are needed for the Region Manager position at Sentry?

To qualify for the Region Manager role at Sentry, you should have a Bachelor’s degree or equivalent work experience, along with at least 2 years of related work experience. Exceptional sales and communication skills are essential, as is the ability to thrive in a remote work environment. A valid driver’s license and an acceptable Motor Vehicle Record are also required, alongside a primary residence within the sales territory.

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What benefits do Region Managers at Sentry receive?

Region Managers at Sentry can expect a comprehensive benefits package that includes a company car with a gas card, ongoing training programs, medical and dental insurance, a robust 401(k) plan with matching contributions, generous paid time off, and the opportunity to further their education with a tuition reimbursement program. Sentry values your well-being through employee assistance programs and encourages community involvement with a gift matching program.

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What is the salary range for a Region Manager at Sentry?

The base salary range for the Region Manager position at Sentry is between $88,900 and $122,200, depending on qualifications and experience. This position also offers additional earning potential through incentives on new and renewal business, making it a financially rewarding career choice.

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What is the company culture like at Sentry for a Region Manager?

Sentry's company culture is built on trust, professional development, and teamwork. As a Region Manager, you'll be part of a long-standing organization recognized as one of the best midsize employers in America. The supportive work environment fosters personal and professional growth, offering a rewarding atmosphere where you can thrive and contribute to collective success.

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Common Interview Questions for Region Manager
How do you plan to motivate your sales team as a Region Manager?

To motivate my sales team as a Region Manager, I would foster open communication, celebrate both small and large successes, and provide the necessary tools and training to maximize their potential. Additionally, creating a positive workplace culture where team members feel valued and supported is essential to drive motivation and performance.

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What strategies would you use to recruit top talent as a Region Manager at Sentry?

I would utilize both traditional and modern recruiting strategies, such as attending industry events, leveraging social media platforms, and creating engaging job postings that highlight Sentry’s culture and opportunities for growth. Building a strong employer brand and showcasing employee testimonials would also be key in attracting top talent.

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Can you describe a time when you successfully managed a team to achieve sales goals?

In my previous role, I led a team through a strategic initiative focusing on upselling existing clients. By establishing clear objectives and implementing targeted training, we exceeded our sales targets by 30% within six months. Analyzing performance data and frequently checking in with team members was crucial to our success.

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How do you handle underperforming team members?

When addressing underperforming team members, I first communicate with them directly to understand any challenges they face. From there, I provide tailored support and resources, set clear performance expectations, and regularly monitor progress. If necessary, I also encourage development opportunities to help them improve their skills.

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What do you believe is essential for teamwork among sales professionals?

Effective communication, trust, and alignment on common goals are essential for teamwork among sales professionals. Fostering a collaborative environment where team members can share ideas, strategies, and challenges contributes to overall team success. Regular meetings to review progress and celebrate achievements also play a crucial role.

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How would you prioritize customer acquisition versus customer retention as a Region Manager?

While customer acquisition is critical for growth, I believe customer retention should also be a top priority. I would implement strategies for both, understanding that loyal customers often lead to referrals and repeat business. Balancing efforts through market analysis and tailored customer engagement would be my approach.

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Describe your approach to maintaining compliance with industry regulations.

I maintain compliance with industry regulations by staying current with changes through professional development and internal audits. I ensure that my team is well-informed about compliance requirements and provide regular training on best practices, thereby fostering a culture of accountability and continuous improvement.

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How do you assess and analyze sales performance metrics?

I assess sales performance metrics by utilizing tools and software to gather data on key performance indicators such as conversion rates, customer acquisition costs, and sales cycle lengths. I review this data regularly to identify trends, successes, and areas for improvement, using it to adjust strategies effectively.

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What techniques would you employ to cultivate long-lasting customer relationships?

To cultivate long-lasting customer relationships, I would focus on personalized communication to understand client needs deeply, proactively addressing any issues, and celebrating milestones in the relationship. Regular check-ins and maintaining transparency in all interactions help build trust and loyalty.

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How do you envision growing Sentry's presence in the North Region?

I envision growing Sentry's presence in the North Region by expanding our outreach efforts, increasing brand awareness through targeted marketing campaigns, and establishing strong local partnerships. Additionally, focusing on community engagement will enhance our reputation and contribute to overall growth in the area.

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As one of the largest and most secure mutual business insurance companies in the nation, we know how important it is to attract—and retain—talented, hardworking individuals. That’s why we offer you opportunities to grow professionally and personal...

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