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Executive Disability Insurance Jobs in Chicago, IL

Executive Assistant

Rosemont, IL · On-site

$27 - $39.50/hr

... Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan ...

Executive Assistant

Orland Park, IL · On-site

$22.80 - $24/hr

We are looking for a highly organized Executive Assistant with relevant experience to support daily ... disability insurance. Hired contract/temporary professionals are also eligible to enroll in our ...

... Disability Insurance Parental Leave Employee Assistance Program (EAP) Traditional and Roth 401(k) with company match Flexible Spending Account (FSA) Employee Stock Purchase Plan at 5% discount ...

Executive Assistant

Rosemont, IL · On-site

$27 - $39.50/hr

... Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan ...

As an Executive Recruiter, you won't just fill positions-you'll directly shape Robinhood ... Employer-paid life & disability insurance, fertility benefits, and mental health benefits. * Time ...

Executive Assistant-BLD *in the Executive Department. The right candidate will provide executive ... Life & Disability Insurance * Vacation, Sick, Personal Time and Company Holidays * Multiple ...

Executive Chef - Plaza

Evanston, IL · On-site

$90K - $100K/yr

Disability Insurance * Retirement Plan * Flexible Time Off Plan * Paid Parental Leave * Holiday Time Off (varies by site/state) * Personal Leave * Associate Shopping Program * Health and Wellness ...

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Showing results 1-20

Executive Disability Insurance information

See Chicago, IL salary details

$27.3K

$96.4K

$189.5K

How much do executive disability insurance jobs pay per year?

As of Aug 21, 2026, the average yearly pay for executive disability insurance in Chicago, IL is $96,372.00, according to ZipRecruiter salary data. Most workers in this role earn between $59,700.00 and $124,100.00 per year, depending on experience, location, and employer.

What is executive disability insurance?

Executive disability insurance is a specialized type of insurance policy designed to protect the income of high-earning executives if they become unable to work due to illness or injury. These policies typically offer higher benefit limits than standard disability insurance to match the executive’s elevated income level. Employers often provide this coverage as part of an executive benefits package to attract and retain top talent. The policy can provide financial stability by covering a significant portion of lost income, helping executives maintain their lifestyle during a period of disability.

What are the key skills and qualifications needed to thrive as an executive disability insurance specialist?

To thrive as an Executive Disability Insurance Specialist, you need a solid understanding of insurance products, risk assessment, and financial planning, typically supported by relevant licenses such as a Life and Health Insurance license. Familiarity with CRM software, underwriting systems, and industry-specific compliance tools is crucial for managing client accounts and applications efficiently. Exceptional interpersonal skills, attention to detail, and trustworthiness help build strong client relationships and navigate complex policy structures. These combined skills are essential for ensuring tailored coverage solutions that protect high-earning clients and foster long-term business growth.

What are some common challenges faced by professionals in executive disability insurance roles when tailoring policies for high-earning clients?

Professionals in Executive Disability Insurance often encounter challenges such as understanding the unique income structures and benefit needs of executives, which can include bonuses, stock options, and deferred compensation. Customizing policies to adequately replace a significant portion of complex compensation packages requires in-depth client consultations and coordination with legal and financial advisors. Additionally, navigating regulatory requirements and ensuring policy compliance can be intricate due to the high-value nature of these policies. Strong communication and analytical skills are essential to address these challenges and build tailored, comprehensive solutions for each client.

What is the difference between Executive Disability Insurance vs Corporate Disability Insurance?

FeatureExecutive Disability InsuranceCorporate Disability Insurance
Target AudienceHigh-level executives and senior professionalsEmployees across various levels within a corporation
Coverage FocusPersonal income protection for executivesEmployee benefit for general staff
Credentials/CertificationsOften tailored for executives, no specific certifications requiredStandard policies for employees, may require employer approval
Work EnvironmentCorporate offices, executive settingsVaried, including office, retail, or industrial environments

Executive Disability Insurance provides tailored income protection for high-level executives, focusing on their unique financial needs. In contrast, Corporate Disability Insurance is a broader employee benefit that covers staff at all levels. While both protect income in case of disability, Executive Disability Insurance offers more personalized coverage suited for top-tier professionals.

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

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

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

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

Executive Assistant

Wintrust Financial

Rosemont, IL • On-site

$27 - $39.50/hr

Other

Medical, Dental, Vision, Life, Retirement

Posted 11 days ago


Wintrust rating

8.0

Company rating: 8.0 out of 10

Based on 20 frontline employees who took The Breakroom Quiz

71st of 171 rated banks


Job description

Executive Assistant

As one of the largest premium finance companies in the country, FIRST Insurance Funding provides full premium finance services, plus additional services built specifically for agencies. We pride ourselves on the variety of incentive programs, services, and technology we offer. This not only helps grow the agents, brokers, and companies we partner with, but also helps them better serve their clients. FIRST Insurance Funding is a subsidiary of Wintrust, a financial services company with more than $66 billion in assets.

Why join us?

  • An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 11 years) and Employee Recommended award by the Globe & Mail (past 6 years)
  • Competitive pay and discretionary or incentive bonus eligible
  • Comprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a few
  • Family-friendly work hours
  • With 200+ community bank locations, we offer opportunities to grow and develop in your career
  • Promote from within culture

Why join this team?

  • We have a culture that encourages an entrepreneurial spirit
  • We offer multiple opportunities for development and upward mobility

The Executive Assistant at First Insurance Funding will be responsible for management of calendars, scheduling of meetings, and coordination of travel for executives. Additional responsibilities include assisting in meeting preparation and event coordination. Ideal candidates will be highly organized, detail-oriented, self-motivated, and enthusiastic individuals who embrace this critical support role and thrive in a client intensive environment.

What You'll Do

  • Managing the daily schedule and travel of CEO, President, and COO.
  • Scheduling and organizing travel itineraries and travel arrangements (airline, hotel, car services). Assisting with expense reports.
  • Assist in setting up/coordinating meetings. Working with vendors on external venues. Coordinating catering and meals for meetings.
  • Keeping Track of monthly executive Meetings. Sending Reminders to Team Members. Creating agenda Deck by collecting and consolidating updates from other executives.
  • Keeping track & Scheduling special events. Putting resources out for meetings. Creating Name Tags for CEO & Team Members.
  • Tracking meetings, agenda setting, gathering information, deck assimilation, designing announcement slides for all company meetings.
  • Support projects for the Managing Sales Directors.
  • Administrative support including filing, copying, and typing correspondence, presentations, spreadsheets, etc.
  • Ability to run and manage business, including but not limited to: ordering and coordinating personal travel including car services, flight reservations, restaurant reservation, etc.
  • Generate and share reports.
  • Coordinate visits of outside guests or candidates.
  • All other tasks as assigned and requested

Qualifications

  • 3-5 years of relevant experience
  • Proven experience of recognizing the necessity of adhering to pre-established timetables without compromising on quality
  • Anticipate the needs of leadership by proactively managing complex calendars
  • Ability to manage seamless logistics for meetings and presentations including booking venues and prepping materials
  • Highly proficient in Microsoft Suite
  • Background in financial or insurance industry a plus
  • High degree of personal integrity to build and maintain trust across senior leadership, internal teams and external partners

Benefits

Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet Insurance

Compensation

The estimated hourly rate for this role is $27.00 - $39.50 along with eligibility to earn an annual bonus. Actual salaries may vary based on several factors, such as a candidate's qualifications, skills and experience.

Wintrust Financial Corporation, including community banking and financial services subsidiaries, is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, disability, veteran status, genetic information, and other legally protected categories.


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