Full-Time
Account Executive
Captive Territory
Updated on 9/4/2026
Sentry Insurance
1,001-5,000 employees
Mutual insurer delivering business insurance coverage
Compensation Overview
$232.7k - $268.7k/yr
Springfield, MO, USA
Remote
Residence within the sales territory is required; regular travel throughout the defined territory is expected.
Bachelor's
 Insurance (1) |
|---|
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- A bachelor's degree or equivalent work experience or related sales experience is required.
- The ability to obtain and maintain the necessary Property and Casualty and Life licenses required to sell Sentry's products is required.
- Residence within the sales territory is required.
- The candidate must have self-discipline and the ability to thrive in a remote work environment.
- The candidate must be able to multitask, prioritize, communicate effectively, and remain organized.
- Strong analytical and math skills are required.
- An acceptable Motor Vehicle Record, a valid driver's license, and the ability to meet travel requirements are required.
- Sell directly to niche market accounts to increase premium volume.
- Retain profitable business by providing effective, quality service to policyholders.
- Build and maintain quality relationships with businesses.
- Work directly with Underwriting, Claims, Loss Control, Audit, Customer Service, and other key partners.
- Call on and pursue all niche market opportunities assigned to the geographic territory.
- Leverage current customers and relationships for new growth and sales opportunities.
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'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
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.
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.
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
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