Enterprise Account Executive Visa Sponsorship Jobs in Wisconsin
Enterprise account executive roles in Wisconsin are concentrated in Milwaukee and Madison, where companies in financial services, manufacturing technology, and SaaS serve mid-market and enterprise clients across the Midwest. Employers like Fiserv, Northwestern Mutual, and Epic Systems have established sales organizations that periodically sponsor H-1B visa and other work visas for qualified international candidates.
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Get Access To All JobsINTRODUCTION
Our highly trained Account Executives present specialized commercial insurance, 401K, and life insurance products that are perfectly designed for the industries we serve.
You’re not just in it to win it. You want to crush it every time. Because that’s what our sales professionals do. Not just anyone has what it takes to build strong and profitable relationships. If you’re a unique performer, Sentry offers a career opportunity that soars beyond commercial insurance sales.
We provide everything you need to carve out a sales career filled with success and purpose, including:
- High earning potential with base salary, commissions, monthly/annual incentives, plus recognition trips
- Outstanding benefits and a 401(k) program matching dollar for dollar up to 8%
- Opportunities for professional development and growth
- Outstanding training and support
- An industry-leading line of products and services
Total currently estimated projected compensation range for this position is $139,676-$175,676, which is a combination of base pay, currently projected renewal commissions, and currently estimated new business commission opportunities. Commission opportunities – both renewal and new business – are based on achievement of sales objectives and compliance with the terms of the applicable incentive plan.
LOCATION
The Wisconsin territory includes: Southeast Wisconsin to include the Milwaukee South Metro. Residence within the sales territory is required.
WHAT YOU’LL DO
- 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 your geographic territory
- Leverage current customers and relationships for new growth and sales opportunities
WHAT IT TAKES
- Bachelor’s degree or equivalent work experience/related sales experience
- The ability to obtain and maintain the necessary P&C, and Life licenses required to sell the products Sentry offers
- Self-discipline and ability to thrive in a remote work environment
- Ability to multitask, prioritize, communicate effectively, and remain organized
- Strong analytical and math skills
- Acceptable Motor Vehicle Record with a valid driver’s license and ability to meet travel requirements
Here is what you can look forward to as part of our team:
At Sentry, your total rewards go beyond competitive compensation. We’re committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both professionally and personally.
Home Office: Enjoy the best of both worlds. With a home office set up and time in the field, with regular travel in your company car in your defined territory. We provide the cutting edge proprietary technology and tools you need to be more efficient and effective in the field including a laptop and cell phone reimbursement.
Continuous Learning: Unlock your potential through Sentry University, including comprehensive, ongoing training, including licensure and take advantage of our tuition reimbursement program.
Comprehensive Benefits: We support your whole self with group medical, dental, and vision insurance along with parental leave, pet insurance, caregiver leave, and wellness resources. Options for HSA, FSA, and Dependent Care FSA are available.
Investing in Your Future: We’re committed to your long-term financial well-being. We offer a 100% company match on the first 8% you contribute to your 401(k) each pay period, and those funds vest immediately.
Giving Back: Through the Sentry Foundation, we’re proud to support the United Way and make a difference in our communities.
WHY JOIN SENTRY?
At Sentry, we believe our people are the heart of our success. We’re proud to be recognized for the culture we’ve built, earning spots on Forbes’ lists for America’s Best Midsize Employers and Best Employers for New Grads, as well as Newsweek’s America’s Greatest Workplaces for Women and Diversity. These honors reflect our commitment to your professional satisfaction and growth.
BUILDING ON A LEGACY
Our future is bright, but it’s anchored in a long history of stability. Since our founding in 1904, we’ve dedicated ourselves to helping businesses protect their futures. That trust has made us one of the largest and most financially stable mutual insurance companies in the U.S. We’re proud to have maintained an A+ rating from A.M. Best, the industry’s leading authority, for over 30 years.
YOUR CAREER, OUR COMMUNITY
Whether you’re working at our headquarters in Stevens Point, Wisconsin, or one of our many offices across the country, you’ll find a challenging and rewarding environment. Explore the Our Teams tab on our Career Page to see the diverse career paths we offer, with a focus on ongoing development and professional growth.
Ready to own your future? Join us at Sentry, opportunities await!
Casey Van Der Geest
Talent Acquisition Specialist
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.
INTRODUCTION
Our highly trained Account Executives present specialized commercial insurance, 401K, and life insurance products that are perfectly designed for the industries we serve.
You’re not just in it to win it. You want to crush it every time. Because that’s what our sales professionals do. Not just anyone has what it takes to build strong and profitable relationships. If you’re a unique performer, Sentry offers a career opportunity that soars beyond commercial insurance sales.
We provide everything you need to carve out a sales career filled with success and purpose, including:
- High earning potential with base salary, commissions, monthly/annual incentives, plus recognition trips
- Outstanding benefits and a 401(k) program matching dollar for dollar up to 8%
- Opportunities for professional development and growth
- Outstanding training and support
- An industry-leading line of products and services
Total currently estimated projected compensation range for this position is $139,676-$175,676, which is a combination of base pay, currently projected renewal commissions, and currently estimated new business commission opportunities. Commission opportunities – both renewal and new business – are based on achievement of sales objectives and compliance with the terms of the applicable incentive plan.
LOCATION
The Wisconsin territory includes: Southeast Wisconsin to include the Milwaukee South Metro. Residence within the sales territory is required.
WHAT YOU’LL DO
- 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 your geographic territory
- Leverage current customers and relationships for new growth and sales opportunities
WHAT IT TAKES
- Bachelor’s degree or equivalent work experience/related sales experience
- The ability to obtain and maintain the necessary P&C, and Life licenses required to sell the products Sentry offers
- Self-discipline and ability to thrive in a remote work environment
- Ability to multitask, prioritize, communicate effectively, and remain organized
- Strong analytical and math skills
- Acceptable Motor Vehicle Record with a valid driver’s license and ability to meet travel requirements
Here is what you can look forward to as part of our team:
At Sentry, your total rewards go beyond competitive compensation. We’re committed to supporting the whole you, which is why we offer a comprehensive package designed to help you thrive both professionally and personally.
Home Office: Enjoy the best of both worlds. With a home office set up and time in the field, with regular travel in your company car in your defined territory. We provide the cutting edge proprietary technology and tools you need to be more efficient and effective in the field including a laptop and cell phone reimbursement.
Continuous Learning: Unlock your potential through Sentry University, including comprehensive, ongoing training, including licensure and take advantage of our tuition reimbursement program.
Comprehensive Benefits: We support your whole self with group medical, dental, and vision insurance along with parental leave, pet insurance, caregiver leave, and wellness resources. Options for HSA, FSA, and Dependent Care FSA are available.
Investing in Your Future: We’re committed to your long-term financial well-being. We offer a 100% company match on the first 8% you contribute to your 401(k) each pay period, and those funds vest immediately.
Giving Back: Through the Sentry Foundation, we’re proud to support the United Way and make a difference in our communities.
WHY JOIN SENTRY?
At Sentry, we believe our people are the heart of our success. We’re proud to be recognized for the culture we’ve built, earning spots on Forbes’ lists for America’s Best Midsize Employers and Best Employers for New Grads, as well as Newsweek’s America’s Greatest Workplaces for Women and Diversity. These honors reflect our commitment to your professional satisfaction and growth.
BUILDING ON A LEGACY
Our future is bright, but it’s anchored in a long history of stability. Since our founding in 1904, we’ve dedicated ourselves to helping businesses protect their futures. That trust has made us one of the largest and most financially stable mutual insurance companies in the U.S. We’re proud to have maintained an A+ rating from A.M. Best, the industry’s leading authority, for over 30 years.
YOUR CAREER, OUR COMMUNITY
Whether you’re working at our headquarters in Stevens Point, Wisconsin, or one of our many offices across the country, you’ll find a challenging and rewarding environment. Explore the Our Teams tab on our Career Page to see the diverse career paths we offer, with a focus on ongoing development and professional growth.
Ready to own your future? Join us at Sentry, opportunities await!
Casey Van Der Geest
Talent Acquisition Specialist
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.
Enterprise Account Executive Job Roles in Wisconsin
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Search Enterprise Account Executive Jobs in WisconsinEnterprise Account Executive Jobs in Wisconsin: Frequently Asked Questions
Which companies sponsor visas for enterprise account executives in Wisconsin?
Milwaukee-based Fiserv and Northwestern Mutual are among the larger Wisconsin employers with established visa sponsorship programs, particularly for enterprise sales roles tied to fintech and financial services. Madison's technology sector, anchored by companies like Epic Systems and a growing cluster of SaaS firms, also produces H-1B filings for sales positions. Sponsorship activity is more common at enterprise-scale employers than at smaller regional firms.
Which visa types are most common for enterprise account executive roles in Wisconsin?
The H-1B is the most common visa category for enterprise account executive roles in Wisconsin, provided the position is structured as a specialty occupation requiring a relevant bachelor's degree or higher. TN visas are available to Canadian and Mexican nationals in qualifying business roles. Candidates already holding an O-1A or L-1 visa may also find Wisconsin employers willing to continue sponsorship, depending on the company's existing legal infrastructure.
Which cities in Wisconsin have the most enterprise account executive sponsorship jobs?
Milwaukee generates the highest volume of enterprise account executive opportunities in Wisconsin, driven by its concentration of financial services firms, insurance companies, and technology vendors serving large institutional clients. Madison is the second-strongest market, particularly in health IT, edtech, and software sales tied to its university-anchored tech ecosystem. Green Bay and Waukesha see occasional openings but at meaningfully lower frequency than the two major metro areas.
How to find enterprise account executive visa sponsorship jobs in Wisconsin?
Migrate Mate is a job board built specifically for international candidates seeking visa sponsorship in the U.S. You can filter directly for enterprise account executive roles in Wisconsin, with listings verified for sponsorship intent. This is more efficient than searching general job boards, where sponsorship status is often unlisted or unclear. Migrate Mate's focus on the sponsorship-eligible segment of the market saves significant research time for candidates in this role category.
Are there any Wisconsin-specific considerations for enterprise account executives seeking visa sponsorship?
Enterprise account executive roles in Wisconsin must meet the Department of Labor's prevailing wage requirements for the Milwaukee or Madison metropolitan areas when tied to an H-1B petition, and those wages reflect local market rates rather than national figures. Wisconsin's enterprise sales market skews toward financial services, manufacturing technology, and healthcare IT, so candidates with domain expertise in those verticals are better positioned. The University of Wisconsin system also produces a pipeline of international talent that some employers are familiar with sponsoring.
What is the prevailing wage for sponsored enterprise account executive jobs in Wisconsin?
U.S. employers sponsoring a visa must pay at least the prevailing wage, which is what workers in the same role, area, and experience level typically earn. The Department of Labor sets this rate to make sure companies aren't hiring foreign workers simply because they'd accept lower pay than a U.S. worker. It varies by job title, location, and experience. You can look up current prevailing wage rates for any occupation and location using the OFLC Wage Search page.