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Sentry Insurance

Mutual insurer delivering business insurance coverage

Transportation Safety Services Consultant 2

Full-TimePosted on 10/16/2026
$82.4k - $123.6k
Mid
Bachelor's
Houston, TX, USA+2 moreMore locations: Dallas, TX, USA | San Antonio, TX, USA
HybridHome office with extensive field travel (60%); travel is mainly in Texas, Mississippi, Oklahoma, and Arkansas.
Insurance

About the job

Requirements
  • A bachelor's degree or equivalent experience with emphasis in the trucking industry is required.
  • A minimum of 2 plus years of advanced knowledge in a safety department in the trucking industry is required.
  • Knowledge of Federal Motor Carrier Safety Administration regulations and fleet safety best practices is required.
  • Certified Director of Safety through NATMI is required, or the candidate must be willing to pursue the designation.
  • An acceptable motor vehicle record and ability to perform extensive travel over a large territory are required.
  • The role requires a high level of independence and self-motivation to work from home and manage a large geographic territory.
  • Effective oral and written communication and human relations skills are required.
Responsibilities
  • Conduct onsite safety consultations for assigned clients while evaluating underwriting acceptability.
  • Recommend safety enhancements and provide technical safety resources to customers.
  • Complete detailed reports for agents and underwriting regarding account profiles, risk-improvement opportunities, and overall opinions of risk.
  • Develop, coordinate, and conduct safety seminars and training programs for customers to promote driver safety awareness and reduce claims.
  • Maintain and demonstrate expertise in Federal Motor Carrier Safety Administration compliance, fleet safety, driver management, safety culture development, general liability, and cargo securement and protection.
  • Travel extensively across a large territory, mainly in Texas, Mississippi, Oklahoma, and Arkansas; travel is 60%.

About the company

Sentry Insurance provides business insurance and retirement plan services to a wide range of industries. It underwrites general liability, commercial property, workers’ compensation, and 401(k) plans, with revenue from selling these insurance and retirement products. It differentiates itself as a mutual insurance group that emphasizes personalized service and long-term relationships, supported by strong financials (assets over $25 billion and an $8 billion policyholder surplus) and an A+ AM Best rating. Its goal is to provide comprehensive risk protection and retirement options to businesses and their employees while maintaining financial security and enduring partnerships.

Company Size

1,001-5,000

Company Stage

N/A

Total Funding

N/A

Headquarters

Stevens Point, Wisconsin

Founded

1904

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Simplify Jobs

Simplify's Take

What believers are saying

  • Sentry completed The General acquisition on January 1, 2025, expanding premium revenue.
  • Sentry launched a 40-month headquarters renovation on April 6, 2026, supporting recruitment.
  • ABC Wisconsin renewed its exclusive insurance program with Sentry, reinforcing contractor distribution.

What critics are saying

  • Wesco sued Sentry in September 2025 over a $1.99 million settlement refusal.
  • Louisiana courts dismissed Sentry from a 2024 crash suit in July 2026, highlighting claims friction.
  • The General integration and Dairyland rebrand create execution risk across 1,300 employees and channels.

What makes Sentry Insurance unique

  • Mutual ownership keeps underwriting discipline focused on policyholder surplus, not quarterly shareholder payouts.
  • The General acquisition made Sentry a scaled non-standard auto player with direct and agent distribution.
  • Forty-month Stevens Point headquarters renovation signals long-term capital commitment and employee retention investment.

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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
Oct 7th, 2026
Sentry Insurance climbs to No. 11 on Deloitte's Wisconsin 75 with $6.9B revenue

Sentry Insurance has been ranked number 11 on Deloitte's Wisconsin 75 list, which recognises the state's largest privately held companies. The mutual insurer climbed to number 529 on the 2026 Fortune 1000, its first appearance in the top 600, with total revenue exceeding $6.9 billion in 2025. Headquartered in Stevens Point, Sentry employs over 3,000 people in Wisconsin. The company received an A+ superior financial strength rating from AM Best for the 35th consecutive year. AM Best cited Sentry's capital strength, innovation, diversified portfolio, and sustainable results. The insurer has also received workplace recognition from Newsweek and Forbes.

Kahler Slater
Apr 7th, 2026
Kahler Slater partners with Sentry Insurance to transform Stevens Point headquarters.

Kahler Slater partners with Sentry Insurance to transform Stevens Point headquarters. April 7, 2026 Kahler Slater is partnering with Sentry Insurance on a comprehensive renovation of its headquarters in Stevens Point, Wisconsin. The multi-year project represents a significant reinvestment in Sentry's campus and a forward-looking vision for the future of work. Originally constructed in 1977, the 1.5 million-square-foot facility is being reimagined to better support today's workforce while honoring the building's legacy. Kahler Slater is leading the design of approximately 800,000 square feet of renovations, focused on enhancing employee experience, increasing flexibility, and strengthening connections across the campus. The transformation introduces a refreshed architectural expression, replacing the existing façade with expanded glazing to bring in natural light and create a more open, welcoming environment. Interior updates include modernized workspaces, collaborative settings, and integrated technology to support hybrid work models and evolving team dynamics. Employee well-being is a central driver of the design. Planned improvements include a reimagined wellness center, updated dining and café spaces, and enhanced outdoor environments that encourage connection and respite throughout the workday. "This renovation will provide an exceptional environment for our employees, creating a headquarters that enhances their experience and supports our efforts to attract top talent to Stevens Point," said Pete McPartland, Sentry Chairman and CEO. Sustainability is also a key priority, with strategies focused on material reuse, energy-efficient systems, and high-performance building upgrades that reduce environmental impact while improving long-term building performance. "Having partnered with Sentry on several projects over the years, we understand the needs and how to accommodate them within the company's culture," said Glenn Roby, Chief Executive Officer at Kahler Slater. "This renovation will create spaces for collaboration, respite, and flexible team growth, all while preserving the cultural touchstones that make this headquarters distinctly Sentry." Construction is currently underway, with phased completion planned to allow continued use of the facility throughout the renovation process.

ABC for Health
Sep 29th, 2025
A Better Way to Insure: The ABC of Wisconsin Insurance Program with Sentry

That's why the Associated Builders and Contractors (ABC) of Wisconsin has partnered exclusively with Sentry Insurance and a select group of independent agencies to offer a specialized insurance program designed for contractors like you.

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 & Large Scale Farmer
Apr 8th, 2025
Sentry expands into the south east with new Kent offices

Sentry expands into the south east with new Kent offices.