1

Insurance Leadership Jobs in Chicago, IL (NOW HIRING)

Being a Leader in and Giving Back to Our Communities * Diversity & Inclusion * Financial Strength ... Take the first step towards operating your own Shelter Insurance Agency today! Applicants must be ...

Being a Leader in and Giving Back to Our Communities * Diversity & Inclusion * Financial Strength ... Take the first step towards operating your own Shelter Insurance Agency today! Applicants must be ...

... leads (Medicare A&B/Medicaid). Requires an active Life & Health license in AZ, IL, MD, MI, NC, NY, OH, PA, TN, TX, or VA. Medicare/AHIP experience preferred; bilingual encouraged. Sell life insurance ...

next page

Showing results 1-20

Insurance Leadership information

See Chicago, IL salary details

$38.6K

$85.3K

$126.2K

How much do insurance leadership jobs pay per year?

As of Aug 10, 2026, the average yearly pay for insurance leadership in Chicago, IL is $85,294.00, according to ZipRecruiter salary data. Most workers in this role earn between $68,500.00 and $102,000.00 per year, depending on experience, location, and employer.

What is the difference between Insurance Leadership vs Insurance Underwriter?

AspectInsurance LeadershipInsurance Underwriter
Required CredentialsTypically requires leadership experience, industry certifications, and sometimes advanced degreesRequires industry certifications like CPCU or AIC, and a relevant bachelor’s degree
Work EnvironmentStrategic, managerial, and cross-departmental focus in corporate settingsAnalytical, detail-oriented work primarily in underwriting departments
Employer & Industry UsageUsed in insurance companies, agencies, and brokerages for leadership rolesCommonly employed in insurance companies, focusing on risk assessment and policy pricing

Insurance Leadership roles focus on strategic decision-making, team management, and overall company direction, often requiring extensive industry experience. Insurance Underwriters concentrate on evaluating risks, setting premiums, and approving policies, with a strong emphasis on analytical skills. While both roles are vital in the insurance industry, they serve different functions and require distinct skill sets.

What are some common challenges faced by professionals in insurance leadership roles, and how can they be addressed?

Insurance leaders often encounter challenges such as adapting to evolving regulations, managing a diverse workforce, and driving digital transformation within their organizations. Successfully addressing these challenges requires strong change management skills, continuous professional development, and fostering open communication across teams. Leaders who prioritize innovation, invest in staff training, and maintain a customer-centric approach are better equipped to navigate industry shifts and guide their organizations toward sustained growth.

What is insurance leadership?

Insurance leadership refers to the roles and responsibilities of individuals who guide and manage insurance organizations or teams. Leaders in this field set strategic direction, oversee operations, ensure compliance with regulations, and drive growth and innovation within the company. They often focus on developing talent, improving customer experience, and adapting to industry changes such as new technologies and evolving risk landscapes. Effective insurance leaders require strong communication, analytical, and decision-making skills to succeed in a dynamic and highly regulated industry.

What are the key skills and qualifications needed to thrive in insurance leadership?

To thrive in Insurance Leadership, you need deep knowledge of insurance products, market trends, and regulatory requirements, typically supported by a degree in business, finance, or a related field and significant industry experience. Familiarity with insurance management platforms, data analytics tools, and relevant certifications such as CPCU or CLU is often expected. Strong strategic thinking, communication, and team management skills distinguish top performers in this role. These capabilities are essential for driving organizational growth, ensuring compliance, and effectively leading teams in a competitive and regulated industry.
What cities near Chicago, IL are hiring for Insurance Leadership jobs? Cities near Chicago, IL with the most Insurance Leadership job openings:
Infographic showing various Insurance Leadership job openings in Chicago, IL as of August 2026, with employment types broken down into 100% Full Time. Highlights an 91% In-person, and 9% Remote job distribution, with an average salary of $85,294 per year, or $41 per hour.

Insurance Investment Sales Leader, North America

bfinance

Chicago, IL • On-site

Full-time

Re-posted 27 days ago


Job description

Salary: Salary depending on experience

About bfinance

bfinance is an award winning specialist consultant that provides differentiated data driven insights and modular end to end investment services to institutional investors around the globe. Founded in 1999, the London headquartered firm has conducted engagements for more than 600 clients in over 45 countries and has 12 offices globally. Services span manager search, strategy development & implementation, ongoing oversight, governance, and program management, empowering clients with the information they need for key decisions making. With fully customised processes tailored to each client, bfinance combines deep sector specific expertise from portfolio management, research, consultancy, and academia with a global perspective, providing clients with a leading partner for data, knowledge, and analysis in investment strategy and implementation. For a brief company history visit: https://www.bfinance.com/who-we-are/celebrating-25-years


Role Overview

bfinanceisseekinga commercially driven investment professional to contribute to the growth of its insurance segment across North America. Globally, insurance remains a strategically important segment, building on a 25-year history; as at end 2025, bfinance had conducted almost 300 assignments for 100+ insurers, of every variety, spanning 24 countries.


This role combines insurance sectorexpertisewith business development responsibilities, with a strong emphasis on originating, developing, and progressing client opportunities within the insurance market.

Working closely with the global insurance team led by Ravi Rastogi, and the CEO, David Vafai, the individual will play an active role in building pipeline, engaging prospective clients, and converting opportunities into revenue over time.

The role is designed to evolve into a full client coverage and revenue ownership position as the individualdemonstratescommercial success.

Success in this role will be measured by contribution to pipeline development, client engagement, and progression toward revenue generation within the insurance segment.

Key Responsibilities

Business Development & Client Engagement

  • Drive origination efforts across the insurance segment, including pipeline development, meeting generation, and opportunity progression
  • Contribute to the development of proposals, pitch materials, and client solutions
  • Lead/Participatein client meetings with senior stakeholders (CIO, CFO, CRO, investment teams), developing credibility over time
  • Representbfinanceat industry events anddrive/support relationship-building efforts across the insurance ecosystem
  • Contribute directly to revenue generation by progressing opportunities through the sales cycle in partnership with North American Directors


Insurance Segment Development

  • Maintain /Develop a strong understanding of the U.S. insurance investment landscape, including regulatory considerations (e.g., NAIC) and portfolio construction approaches
  • Extendmarket intelligence across insurers, asset managers, and key industry participants
  • Support the development of insurance-specific insights, thought leadership, and client-facing content
  • Partner with global insurance leadership and research teams to translate technical capabilities into market-relevant positioning
  • Help define target client segments andprioritizationstrategy within the U.S. insurance market


Platform Collaboration

  • Coordinate closely with global research, advisory, and implementation teams to support client opportunities
  • Ensure alignment between insurance segment priorities and broader North American commercial strategy
  • Contribute to internal planning discussions related to segment development and growth

Candidate Profile

Experience

  • Typically7+ years of experience ininsurance asset management origination roles.
  • Background may include:(a) Insurance investment teamswithin an insurance company; (b) Asset management (insurance coverage or solutions/ salesroles); (c) Investment consulting or advisorywith a demonstrable growth element
  • Familiarity with insurance asset allocation, governance, and regulatory frameworks (e.g., NAIC)


Skills & Attributes

  • Demonstrated interest or experience in business development, client engagement, or revenue generation
  • Strong interest inexpandingexpertisewithin the insurance segment
  • Ability to communicate effectively with both technical and commercial stakeholders
  • Collaborative approach, with the ability to work across teams and geographies
  • Self-starter with a proactive and entrepreneurial mindset


Education

  • Bachelors degreerequired; CFA or CAIA (or progress toward) preferred


Additional Information

  • Willingness to travel across North America and internationally.
  • Compensation will reflect the commercial nature of the role and include performance-based incentives.


bfinanceoperates in the United States through a registered broker-dealer and registered investment adviser structure. Individuals in this role maybe requiredto obtain andmaintainapplicable FINRA registrations and licenses, unless already appropriately licensed.

  • Required licenses may include Series 7, Series 63/65/66, Series 82, or other registrations depending on role responsibilities.
  • bfinancewill sponsor and support licensing whererequired.
  • Continued employment is contingent uponmaintainingrequired registrations and compliance with regulatory standards.