Sentry Insurance

Sentry Insurance

Mutual insurance group offering diverse coverage

About Sentry Insurance

Simplify's Rating
Why Sentry Insurance is rated
B-
Rated C on Competitive Edge
Rated B on Growth Potential
Rated B on Differentiation

Industries

Financial Services

Company Size

1,001-5,000

Company Stage

N/A

Total Funding

N/A

Headquarters

Stevens Point, Wisconsin

Founded

1904

Overview

Sentry Insurance provides a range of insurance products tailored for various industries, including transportation, manufacturing, construction, and auto dealerships. Their offerings include general liability, commercial property, workers' compensation, and 401(k) plans. Sentry's products work by providing financial protection against risks associated with business operations and employee welfare. What sets Sentry apart from its competitors is its focus on personalized service and building long-term relationships with customers, which has contributed to its strong financial standing, with over $25 billion in assets. The company's goal is to ensure comprehensive protection for businesses while maintaining a high level of customer satisfaction.

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Simplify's Take

What believers are saying

  • Sentry's acquisition of The General enhances its position in the non-standard auto market.
  • Recognition as a top workplace attracts talent and improves employee retention.
  • Expansion into the southeast with new Kent offices broadens market reach.

What critics are saying

  • Rising litigation and multi-million-dollar verdicts could increase liability costs for clients.
  • Integration challenges from The General acquisition may pose financial risks.
  • Economic uncertainty and inflation could affect the financial stability of Sentry's clients.

What makes Sentry Insurance unique

  • Sentry Insurance offers personalized service and long-term customer relationships.
  • The company has a strong financial position with over $25 billion in assets.
  • Sentry's diverse product range includes 401(k) plans, general liability, and workers' compensation.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

401(k) Retirement Plan

401(k) Company Match

Unlimited Paid Time Off

Meal Benefits

Parental Leave

Mental Health Support

Tuition Reimbursement

Hybrid Work Options

Company News

PR Newswire
May 5th, 2025
60% Of Large Companies Expect No Growth, Sentry Survey Finds

82% of executives at large businesses say they're more stressed in 2025 than last year, citing supply chain disruptions and economic uncertaintySTEVENS POINT, Wis., May 5, 2025 /PRNewswire/ -- In a new report released by Sentry, a leading business insurer, 60% of executives at large businesses reveal they expect their companies to remain flat or shrink in 2025.The report, based on a survey of 1,100 business owners, CEOs, CFOs, and CROs at U.S. companies, was conducted by Wakefield Research on behalf of Sentry. It revealed that 82% of large business leaders are more stressed in 2025 than last year—a figure that's 15 percentage points higher than that reported by leaders at smaller organizations.Large companies seek flexibility to adapt their operations to a heightened and often uncertain risk environment. Post this 60% of large business leaders expect their company to remain stable or shrink in 2025.Reflecting upon their higher stress levels in 2025, C-suite leaders of large companies cite several risks facing their companies—leading many to suggest a focus on stability and cost-control.Top threats according to large business leaders:Economic concerns: Nearly half (45%) of executives cite supply chain issues as their biggest worry, alongside economic uncertainty (39%) and inflation (34%).Nearly half (45%) of executives cite supply chain issues as their biggest worry, alongside economic uncertainty (39%) and inflation (34%). External threats: A vast majority (84%) say they view rising litigation and multi-million-dollar verdicts as a growing problem in their industry. More than one-third also cited cyberattacks (37%) and severe weather events (35%) as top threats.Large companies' responses to threats:Asking more of workers: As 60% of executives at large companies expect their businesses to remain flat or shrink, 55% admit they're asking current employees to work longer hours or take fewer breaks

Farm Contractor Magazine
Apr 8th, 2025
Sentry expands into the south east with new Kent offices

Sentry expands into the south east with new Kent offices.

KTBS
Mar 18th, 2025
Sentry named by Newsweek as a top workplace for women

Sentry named by newsweek as a top workplace for women.

PR Newswire
Feb 25th, 2025
Sentry Earns Spot On America'S Best Employers List

Forbes once again recognizes Wisconsin-based mutual insurerSTEVENS POINT, Wis., Feb. 25, 2025 /PRNewswire/ -- Sentry Insurance continues to be recognized as a workplace leader, earning a repeat designation from Forbes as one of America's Best Midsize Employers.In partnership with analytics firm Statista, Forbes selected this year's honorees based on an independent survey of 217,000 workers across the country. Employees rated their companies on key factors such as work environment, growth opportunities, and diversity. Sentry is one of just 498 companies nationwide to earn a spot on the list, which recognizes employers with 1,000–5,000 employees.This marks the sixth time Sentry has earned this recognition."Our employees make Sentry a great place to work," said Pete McPartland, Sentry's Chairman and CEO. "They've built and sustained a culture that puts people first—whether it's supporting our customers, communities, or each other. This recognition belongs to them.""It's also a credit to the generations before us who laid the foundation for our success," he added

PR Newswire
Feb 3rd, 2025
67% Of Executives More Stressed In 2025: Sentry Survey Finds

Economic uncertainty, workforce challenges, and litigation loom large for business leadersSTEVENS POINT, Wis., Feb. 3, 2025 /PRNewswire/ -- A new survey released by Sentry, a leading business insurer, paints a revealing picture of what's keeping executives up at night in 2025. While nearly half (47%) of business leaders are optimistic their companies will thrive this year, a majority (67%) admit they're feeling more stressed compared to last year

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