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Insurance Executive Jobs in Chicago, IL (NOW HIRING)

Empowered Staffing

Account Executive

Skokie, IL · On-site

Empowered Staffing is partnered with a growing employee benefits and insurance advisory firm known ... You will lead executive-level conversations, develop creative solutions, oversee the supporting ...

Robert Half

Executive Assistant

Itasca, IL · On-site

$90K - $110K/yr

This position offers a salary of $90,000-$110,00 + health, vision, dental insurance + 401K w/match + PTO and more. Responsibilities: * Oversee intricate executive calendars, align competing ...

Wintrust

Executive Assistant

Rosemont, IL · On-site

$27 - $39.50/hr

FIRST Insurance Funding is a subsidiary of Wintrust, a financial services company with more than ... We offer multiple opportunities for development and upward mobility The Executive Assistant at ...

Wintrust

Executive Assistant

Rosemont, IL · On-site

$27 - $39.50/hr

FIRST Insurance Funding is a subsidiary of Wintrust, a financial services company with more than ... We offer multiple opportunities for development and upward mobility The Executive Assistant at ...

Cimcor, Inc.

Executive Assistant

Merrillville, IN

Cimcor, Inc. is seeking a highly capable, detail-oriented Executive Assistant to provide direct ... Medical, dental, and vision insurance * Paid time off & holidays * Mileage and travel reimbursement ...

Cimcor, Inc.

Executive Assistant

Merrillville, IN · On-site

Cimcor, Inc. is seeking a highly capable, detail-oriented Executive Assistant to provide direct ... Medical, dental, and vision insurance * Paid time off & holidays * Mileage and travel reimbursement ...

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Showing results 21-40

All JobsInsurance JobsInsurance Executive JobsInsurance Executive Jobs in Chicago, IL

Insurance Executive information

See Chicago, IL salary details

$11.3K

$104.6K

How much do insurance executive jobs pay per year?

As of Sep 6, 2026, the average yearly pay for insurance executive in Chicago, IL is $103,095.00, according to ZipRecruiter salary data. Most workers in this role earn between $103,100.00 and $103,100.00 per year, depending on experience, location, and employer.

What does an insurance executive do?

The responsibilities of an insurance executive, also known as an insurance broker or insurance account executive, include understanding insurance laws, ensuring companies are abiding by all regulations, providing excellent customer service to the clients of insurance companies, and selling them the most suitable policies. As an insurance executive, you work with the legal department to stay updated on government regulations, assist with mergers and each business acquisition, provide presentations to each new client, and set and achieve sales targets. Other duties include managing the budget and profit/loss margins. You also determine each customer’s needs, for both businesses and individuals, and advise the best insurance policy for their unique situation. This position requires traveling to visit clients.

What does an insurance executive do?

An Insurance Executive is a high-level professional responsible for overseeing the operations, strategy, and growth of an insurance company or department. Their duties often include managing teams, developing business strategies, ensuring compliance with industry regulations, and maintaining relationships with key clients or partners. Insurance Executives play a critical role in decision-making, risk management, and driving profitability within their organizations. They may also be involved in product development and market analysis to ensure their company remains competitive.

What are the key skills and qualifications needed to thrive as an insurance executive, and why are they important?

To thrive as an Insurance Executive, you need a deep understanding of insurance products, risk assessment, regulatory compliance, and business management, typically backed by a bachelor’s degree in business, finance, or a related field. Familiarity with CRM systems, data analytics tools, and relevant certifications such as Chartered Property Casualty Underwriter (CPCU) or Certified Insurance Counselor (CIC) is highly valuable. Exceptional leadership, negotiation, and strategic communication skills distinguish top performers in this role. These competencies enable Insurance Executives to drive business growth, ensure regulatory adherence, and lead high-performing teams in a competitive industry.

What are some common challenges faced by insurance executives when leading cross-functional teams?

Insurance Executives often oversee teams that include underwriting, claims, sales, and compliance professionals, which can present challenges in aligning diverse priorities and communication styles. Successfully managing these teams requires strong leadership skills, the ability to resolve conflicts, and a focus on fostering collaboration to achieve shared business goals. Regularly facilitating clear communication and setting unified objectives are essential practices, helping to ensure all departments work cohesively toward company growth and client satisfaction.

What is the difference between Insurance Executive vs Insurance Agent?

AspectInsurance ExecutiveInsurance Agent
CredentialsTypically requires industry experience, possibly advanced certificationsRequires licensing and certification specific to insurance products
Work EnvironmentCorporate offices, management roles, strategic planningFieldwork, client meetings, sales-focused environment
Employer & Industry UsageInsurance companies, corporate sectorsIndependent agencies, insurance firms, brokers
Common Search & ComparisonHigh-level management, strategic rolesSales, customer service, client acquisition

Insurance Executives focus on strategic management and overseeing company operations, often requiring extensive industry experience. Insurance Agents primarily handle client interactions, sales, and policy sales, requiring licensing. While both roles are vital in the insurance industry, they differ significantly in responsibilities, work environment, and career focus.

More about Insurance Executive jobs

What are the most commonly searched types of Insurance jobs in Chicago, IL?

The most popular types of Insurance jobs in Chicago, IL are:

What are popular job titles related to Insurance Executive jobs in Chicago, IL?

For Insurance Executive jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Insurance Executive jobs in Chicago, IL look for?

The top searched job categories for Insurance Executive jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Insurance Executive jobs?

Cities near Chicago, IL with the most Insurance Executive job openings:

Insurance Executive jobs near you
Infographic showing various Insurance Executive job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 73% Full Time, 21% Part Time, and 5% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $103,095 per year, or $49.6 per hour.

Corporate Sales Account Executive - Chicago

Goosehead Insurance

Chicago, IL • On-site

$100K/yr

Other

Medical, Dental, Vision, Life, Retirement, PTO

Posted 6 days ago

Goosehead Insurance rating

7.4

Company rating: 7.4 out of 10

Based on 14 frontline employees who took The Breakroom Quiz

235th of 315 rated insurance

Job description

Working at Goosehead

We've worked hard to earn the trust of our clients, so we are highly selective in our hiring process. If you think you have what it takes to grow with our company, we would love to meet you.

Since 2003, Goosehead Insurance has been disrupting the insurance industry by giving clients the power of choice, utilizing a smarter marketing approach, and delivering world class service. This is all powered by our focus on hiring and retaining extraordinary people.


Principal Duties and Responsibilities

  • The primary responsibility of an Account Executive is to build a book of business through:
  • Prospecting and establishing referral partner relationships with professionals from the real estate and mortgage industry.
  • Work with clients to understand their insurance needs, analyze options with a large carrier portfolio, and provide a custom solution to mitigate household risk.


Compensation Summary

The Account Executive position has a first-year average on-target earnings of $100,000. Our compensation package consists of a base salary plus uncapped variable commissions, uncapped monthly bonuses and a one-time conditional launch bonus.


Licensing, Training, and Position Requirements:

  • Goosehead will cover one-time costs of all training courses and exam fees to obtain your insurance license
  • This role is contingent on you passing your licensing exam, obtaining the state issued license, and successfully completing the Goosehead training program, which will commence on your start date
  • Account Executives are equipped with extensive training in salesforce.com, sales process management, business development and more, no previous experience is required.
  • Professional development opportunities from the Account Executive role include, but are not limited to, corporate leadership, flexibility with a proven track record, and an apprenticeship program leading to business ownership.


Benefits Summary

  • Comprehensive health, vision, disability, life, and dental insurance programs
  • 401K Matching Plan
  • Employee Stock Purchase Plan
  • Paid holidays, vacation, and sick leave


Experience and Education

  • Bachelor’s degree, 3.0 GPA preferred.
  • Passing the state licensing exam, once hired
  • Legally authorized to work the United States


Preferred Skills, Abilities, Soft Skill Factors

  • Exceptional written and verbal communication
  • Experience in a fast-paced work environment
  • B2B or B2C sales experience or related college major
  • Competitive attitude
  • Networking abilities
  • Entrepreneurial spirit
  • Problem-solving mentality
  • Self-motivated, proactive, and ready to take initiative
  • Strong time management
  • Strong attention to detail and organization
  • Results-driven and committed to continuous improvement
  • High integrity and honest communication


Equal Employment Opportunity

Goosehead is an equal opportunity employer and complies with all applicable federal, state, and local laws, rules, guidelines, and regulations. Goosehead strictly prohibits and does not tolerate unlawful discrimination against employees, applicants, or any other covered person because of race, color, religion, creed, national origin, ancestry, ethnicity, sex (including pregnancy, childbirth, and related medical conditions), sexual orientation, gender, gender identity, transgender status, age, physical or mental disability, veteran status, uniformed service, genetic information, or any other characteristic protected by applicable law. All applicants for employment and all Goosehead employees are given equal consideration based solely on job-related factors, such as qualifications, experience, performance, and availability.


To learn more about our job opportunities, apply here. We look forward to speaking with you!

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