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Executive Insurance Controller Jobs in Chicago, IL

CFS

Controller

Schaumburg, IL · On-site

Controller Schaumburg, Illinois (100% Onsite) $120,000 - $140,000 plus 10-15% performance bonus Our ... insurance organization where you'll partner directly with executive leadership and present ...

Calqulate

Corporate Controller

Crystal Lake, IL

President / CEO Employment Type: Full-Time About the Role We are seeking a hands-on, strategic ... Compliance, Insurance & Asset Management: Oversee corporate risk management, including annual ...

New

Triple-S Steel

Controller

Melrose Park, IL

$100K - $150K/yr

Health insurance (medical, dental, and vision) * Flex Saving Account and Health Reimbursement ... Provide key insights and strategic support to executive leadership * Lead and mentor Staff ...

Triple-S Steel

Controller

Melrose Park, IL · On-site

$100K - $150K/yr

Health insurance (medical, dental, and vision) * Flex Saving Account and Health Reimbursement ... Provide key insights and strategic support to executive leadership * Lead and mentor Staff ...

Cherry Bekaert

Controller

Chicago, IL · Hybrid

$164K - $285K/yr

As a key partner to executive leadership, the Controller will play a critical role in ensuring ... insurance; generous Paid Time Off; retirement plans; Paid Care Leave; and other programs that are ...

Path Construction

Controller

Arlington Heights, IL · On-site

$100K - $160K/yr

Analysis of Corporate Insurance program * Analysis of financials for tax strategies * Analysis of ... Should have experience in partnering with an executive team, and have a high level of written and ...

Path Construction

Controller

Arlington Heights, IL

$100K - $160K/yr

Analysis of Corporate Insurance program * Analysis of financials for tax strategies * Analysis of ... Should have experience in partnering with an executive team, and have a high level of written and ...

Path Construction

Controller

Arlington Heights, IL · On-site

$100K - $160K/yr

Analysis of Corporate Insurance program * Analysis of financials for tax strategies * Analysis of ... Should have experience in partnering with an executive team, and have a high level of written and ...

Lighthouse Autism Center

Controller

Schaumburg, IL · Hybrid

As a member of the Executive Leadership Team (ELT), this role partners closely with the Chief ... Manage corporate insurance renewals related to medical, dental, worker's compensation, and business ...

Lighthouse Autism Center

Controller

Schaumburg, IL · On-site

As a member of the Executive Leadership Team (ELT), this role partners closely with the Chief ... Manage corporate insurance renewals related to medical, dental, worker's compensation, and business ...

Lighthouse Autism Center

Controller

Schaumburg, IL · On-site

As a member of the Executive Leadership Team (ELT), this role partners closely with the Chief ... Manage corporate insurance renewals related to medical, dental, worker's compensation, and business ...

Aspen Guard LLC

Controller

Chicago, IL · On-site

$135K - $165K/yr

Provide strategic financial insights to the executive team, supporting decision-making and business ... Access to our medical insurance plan, which provides coverage for medical expenses and ...

Aspen Guard LLC

Controller

Chicago, IL · On-site

$135K - $165K/yr

Provide strategic financial insights to the executive team, supporting decision-making and business ... Access to our medical insurance plan, which provides coverage for medical expenses and ...

Smartstop-Self-Storage

Controller - Onsite

Lake Forest, IL · On-site

$162 - $198/hr

Reports positive and negative variances to key executives. * Oversees the preparation of federal ... Health insurance including medical, dental and vision * Life and Disability Insurances * Paid Time ...

Trova

Controller - Addison, IL

Saint Charles, IL

$80K - $120K/yr

... executive leadership to strengthen profitability, improve working capital, and support smart ... insurance providers) * Working knowledge of compliance expectations, including applicable ...

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All JobsInsurance Controller JobsExecutive Insurance Controller JobsExecutive Insurance Controller Jobs in Chicago, IL

Executive Insurance Controller information

See Chicago, IL salary details

$11.3K

$104.6K

How much do executive insurance controller jobs pay per year?

As of Aug 21, 2026, the average yearly pay for executive insurance controller in Chicago, IL is $103,014.00, according to ZipRecruiter salary data. Most workers in this role earn between $103,000.00 and $103,000.00 per year, depending on experience, location, and employer.

What is an executive insurance controller?

Executive Insurance Controllers are senior financial professionals who oversee the accounting, financial reporting, and regulatory compliance functions within an insurance company. They are responsible for managing budgets, ensuring accurate financial statements, and implementing internal controls to safeguard company assets. Additionally, they work closely with executive leadership to develop financial strategies, assess risk, and ensure the organization adheres to industry laws and regulations. Their expertise is vital for maintaining the financial health and integrity of the insurance company.

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

To thrive as an Executive Insurance Controller, you need expertise in financial management, insurance accounting, regulatory compliance, and typically a bachelor's degree in finance, accounting, or a related field, often accompanied by CPA or similar certification. Familiarity with financial reporting software, insurance management systems, and advanced Excel skills is crucial. Strong analytical thinking, leadership, and effective communication are key soft skills that set top performers apart. These competencies ensure accurate financial oversight, regulatory adherence, and strategic decision-making essential for organizational success in the insurance industry.

What are some common challenges faced by executive insurance controllers when managing cross-departmental financial reporting?

Executive Insurance Controllers often need to coordinate financial data from multiple departments, such as claims, underwriting, and compliance. One common challenge is ensuring consistency and accuracy across diverse data sources, which may use different systems or reporting standards. Building strong relationships and clear communication channels with department heads is essential to streamline data collection and resolve discrepancies quickly. Proficiency in insurance-specific accounting regulations and financial software also helps address these challenges effectively.

What is the difference between Executive Insurance Controller vs Insurance Manager?

AspectExecutive Insurance ControllerInsurance Manager
CredentialsCPA, CPCU, or similar certifications often preferredRelevant insurance or finance certifications, such as CPCU or ARM
Work EnvironmentStrategic, high-level financial oversight within insurance companies or large corporationsOperational management of insurance teams, policy administration, and claims
Employer & Industry UsageInsurance firms, large corporations with internal insurance departmentsInsurance companies, brokerage firms, corporate risk management
Search & Comparison IntentUnderstanding executive-level insurance finance rolesManaging insurance operations and policies

The Executive Insurance Controller focuses on high-level financial oversight, compliance, and strategic planning within insurance organizations, often requiring advanced certifications. In contrast, an Insurance Manager handles day-to-day operations, policy management, and team supervision. Both roles are vital but differ in scope, responsibilities, and seniority within the insurance industry.

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

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

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

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

Executive Insurance Controller jobs near you

Controller

CFS

Schaumburg, IL • On-site

Full-time

Medical, Life, Retirement, PTO

Re-posted 12 days ago

Job description

Controller

Schaumburg, Illinois (100% Onsite)
$120,000 – $140,000 plus 10–15% performance bonus

Our client, is seeking an experienced Controller to lead the organization's accounting and financial reporting function. This is a highly visible leadership opportunity with a stable, mission-driven fraternal insurance organization where you'll partner directly with executive leadership and present financial results to the Board of Directors. The role is heavily focused on financial analysis, planning, and strategic leadership rather than day-to-day transactional accounting, making it an ideal opportunity for an experienced insurance accounting professional looking to make a meaningful impact.

Why Consider This Opportunity for the Controller?

  • Immediate opening due to a planned leadership transition
  • Highly visible role partnering directly with executive leadership and the Board
  • Strategic position focused on forecasting, financial planning, and business analysis
  • Lead the accounting function while mentoring a collaborative, high-performing team
  • Stable, mission-driven fraternal insurance organization with excellent employee retention
  • Outstanding benefits including:
    • Four weeks of vacation to start
    • Five personal days and five sick days
    • 90% employer-paid medical insurance
    • 401(k) with company-funded annuity contribution
    • Company-paid life insurance
    • 10–15% annual performance bonus

Key Responsibilities for the Controller

  • The Controller will lead the monthly, quarterly, and annual financial reporting process
  • Own the review and approval of the balance sheet, income statement, journal entries, and supporting documentation
  • Develop operating plans, budgets, forecasts, and financial analyses for executive leadership and the Board
  • Present financial results, forecasts, and strategic recommendations to senior leadership and Board members
  • Oversee the accounting team while providing guidance, mentorship, and constructive feedback
  • Partner cross-functionally to improve financial processes and support organizational initiatives
  • Coordinate annual audits and ensure compliance with insurance accounting requirements
  • Drive financial analysis and planning initiatives that support organizational decision-making

Qualifications for the Controller

  • Bachelor's degree in Accounting, Finance, Economics, Mathematics, or a related field
  • 10+ years of progressive accounting or finance experience
  • Insurance industry accounting experience is required
  • Audit background is a plus
  • Strong Microsoft Excel and Microsoft Access skills
  • Experience presenting financial information to executive leadership or Boards of Directors
  • Analytical, collaborative, and comfortable working in a small, "all hands on deck" environment
  • CPA is not required

This is an outstanding opportunity for an experienced insurance accounting professional seeking a strategic leadership role with significant visibility, executive partnership, and the ability to influence the financial direction of a well-established organization.

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