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First Insurance Funding Jobs in Chicago, IL (NOW HIRING)

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 $66 billion in assets. Why join us? * An award-winning culture! We are rated a Top Workplace by the ...

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 $66 billion in assets. Why join us? * An award-winning culture! We are rated a Top Workplace by the ...

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 $66 billion in assets. Why join us? * An award-winning culture! We are rated a Top Workplace by the ...

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 $66 billion in assets. Why join us? * An award-winning culture! We are rated a Top Workplace by the ...

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 ...

Collections Rep

Rosemont, IL · On-site

$20.19 - $26/hr

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 ...

Collections Rep

Rosemont, IL · On-site

$17.25 - $22.25/hr

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 ...

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 ...

Associate Loan Executive

Northbrook, IL · On-site

$19 - $22.60/hr

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 ...

Area Sales Manager

Chicago, IL · On-site

$60K - $125K/yr

Western Funding, a dynamic and fast-growing auto finance company, believes in PEOPLE with the ... Guaranteed compensation of $5,000 per month during the first 12 months of employment.

... first call resolution. Provide insurance coverage, verification details prior authorization statues and alternate funding options for existing and newly launched products. Provide offices with ...

Medical (including Rx), dental, vision on day one of employment * 401(k) with matching funds * 12 ... Pension plan, life insurance, disability insurance, and more. The Flexco team is interested in you ...

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Showing results 1-20

First Insurance Funding information

See Chicago, IL salary details

$25.2K

$59.8K

$119K

How much do first insurance funding jobs pay per year?

As of Sep 2, 2026, the average yearly pay for first insurance funding in Chicago, IL is $59,802.00, according to ZipRecruiter salary data. Most workers in this role earn between $41,200.00 and $71,600.00 per year, depending on experience, location, and employer.

What is First Insurance Funding?

First Insurance Funding is a leading provider of premium finance solutions for the insurance industry. They work with insurance agents and brokers to offer clients flexible payment options for their insurance premiums, making it easier for businesses and individuals to manage their cash flow. By financing insurance premiums, First Insurance Funding helps clients avoid large upfront payments and instead pay over time, which can be especially beneficial for managing budgets and maintaining coverage. Their services cover a wide range of commercial, personal, and specialty insurance lines.

How does a role at First Insurance Funding typically interact with brokers and clients during the premium financing process?

At First Insurance Funding, team members regularly collaborate with insurance brokers and clients to facilitate premium finance agreements. You’ll be expected to provide clear communication, answer questions about payment plans, and ensure all documentation is accurate and compliant with regulations. Building strong relationships with brokers is essential, as they rely on your expertise to deliver seamless financing solutions to their clients. Attention to detail and responsiveness are key for success in this fast-paced, client-focused environment.

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

To thrive as an Insurance Funding Specialist, you need a solid understanding of finance, insurance products, and risk assessment, typically supported by a degree in finance, business, or a related field. Familiarity with loan management software, insurance policy management systems, and regulatory compliance tools is often required. Strong analytical thinking, attention to detail, and effective communication help professionals excel in client interactions and complex documentation tasks. These skills ensure accurate funding processes, regulatory compliance, and high client satisfaction in a competitive financial services environment.

What is the difference between First Insurance Funding vs Insurance Underwriter?

AspectFirst Insurance FundingInsurance Underwriter
CredentialsTypically requires insurance licensing and financial knowledgeRequires insurance licenses, underwriting certifications, and risk assessment skills
Work EnvironmentOffice-based, financial and insurance industry settingOffice or remote, insurance companies or brokerage firms
Industry UsageUsed in insurance funding, premium financing, and financial servicesUsed in evaluating insurance applications, assessing risk, and setting policy terms

First Insurance Funding and Insurance Underwriters both operate within the insurance industry, but their roles differ. First Insurance Funding focuses on providing financial solutions like premium financing, while Insurance Underwriters assess risk to determine policy terms. Understanding these differences helps job seekers and employers identify the right career path or hiring needs within the insurance sector.

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

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

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

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

Infographic showing various First Insurance Funding 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 $59,802 per year, or $28.8 per hour.

Executive Assistant

Wintrust Financial

Rosemont, IL • On-site

$27 - $39.50/hr

Other

Medical, Dental, Vision, Life, Retirement

This job post has expired today. Applications are no longer accepted.


Wintrust rating

8.0

Company rating: 8.0 out of 10

Based on 20 frontline employees who took The Breakroom Quiz

72nd of 174 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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