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Full Time 18
Chicago regional sales leader Illinois

21 regional sales leader jobs found in Chicago, IL

Badger Mutual Insurance
05/05/2026  
Trust Advisor (Illinois) Featured
$84,000 - $110,000 yearly
At Badger Mutual, we believe insurance is more than numbers—it’s about people. Our success is built on strong partnerships, clear communication and a deep understanding of our agency partners’ needs. We are seeking a hands-on Trust Advisor with a strong underwriting mindset to help us drive profitable growth across Illinois. This role is ideal for a sales leader who thrives at the intersection of relationship management, risk evaluation and disciplined growth.   What Will You Do?   »      Build and maintain strong relationships with independent agents, serving as both a sales partner and an underwriting resource »      Evaluate new business opportunities and competitive positioning with underwriting discipline to achieve sustainable growth »      Collaborate closely with underwriting departments to reinforce guidelines while applying sound judgement in the field »      Represent the company at industry events, agency visits,...
Badger Mutual Insurance Remote (Chicago, IL)
WTW
05/03/2026  
Mid-Market Director – Absence, Disability Management and Leave (ADML)
Overview  WTW is launching a new Mid-Market ADML delivery model focused on clients in the 500 to 5,000 life segment. As part of this strategy, we are establishing a new Mid-Market Director role aligned to each of WTW’s six U.S. geographic regions.  Each Mid-Market Director will have primary responsibility for ADML delivery, market leadership, and client success within their assigned geography.  This is a new role that requires flexibility, comfort with ambiguity, and an entrepreneurial mindset to help build, scale, and refine a differentiated mid-market offering.  The Role Own ADML delivery for mid-market clients (500–5,000 lives) within an assigned U.S. geography  Serve as the senior day-to-day ADML leader for assigned relationships, ensuring high-quality delivery and client satisfaction  Lead projects involving the design and management of absence, disability, leave, life, and AD&D programs  Apply deep expertise across claims,...
WTW Chicago, IL Full Time
HUB International
05/01/2026  
National Employee Benefits Practice Leader
ABOUT US     At   HUB International , we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to   maintain   their own unique, regional culture while   leveraging   support and resources from our corporate centers of excellence.        HUB is   one of the   largest global insurance and employee benefits   broker , providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over   $5 billion   in revenue and almost   20,000 employees   in 600 offices throughout North America, HUB has   grown substantially, in   part due to our...
HUB International Chicago, IL Full Time
WTW
02/01/2026  
Senior Director, Executive Compensation and Board Advisory
Summary As a Senior Director in the Executive Compensation and Board Advisory practice you will be primarily responsible for selling, leading and delivering large client engagements and serving as a strategic advisor to clients in your areas of subject matter expertise. You’ll also contribute your thought leadership to the overall development of the Executive Compensation practice and act as a coach and mentor for fellow colleagues. Specific client engagements could include the following: Executive compensation benchmarking Short and long-term incentive design Compensation Committee advice/support Board Advisory Working closely with colleagues in other Work & Rewards practices to sell and deliver on broader rewards strategy projects, including our broad-based employee solutions (compensation, careers, skills, etc.), and our proprietary data and software solutions Partnering with colleagues in our other Health, Wealth, and Career...
WTW Chicago, IL Full Time
HUB International
08/24/2025  
Senior Account Manager and Team Lead - Commercial Lines
About HUB    In a rapidly changing world, HUB advises businesses and individuals on how to prepare for the unexpected. As one of the world’s largest insurance brokers, our focus is dedicated to providing our customers with the peace of mind that what matters most will be protected — through unrelenting advocacy and tailored insurance solutions that put our clients in control. Our growing team of professionals across North America represents a broad, deep, and one-of-a kind aggregation of entrepreneurs and leaders recognized for their excellence throughout the insurance community.     Why Choose HUB?    Throughout our network of more than 550 HUB offices in North America, we offer a competitive, exciting, and friendly work environment that strategically positions our employees for longevity and success. At HUB, we believe in investing in the future of our employees and provide continuous opportunities for growth and development .   Our entrepreneurial culture fosters an...
HUB International Chicago, IL Full Time
AIG
06/25/2025  
Senior Executive Underwriter, AIGRM
At AIG, we are reimagining the way we help customers to manage risk. Join us as a Senior Executive Underwriter to play your part in that transformation. It’s an opportunity to grow your skills and experience as a valued member of the team. Make your mark in AIG Risk Management, AIGRM. AIG underwriting teams help to find insurance solutions in areas including Financial Lines, Property, Casualty, Specialty Lines, Cyber, Multinational Clients, and High Net Worth individuals. We are reimagining how we help customers to manage risk, transforming our operating model, and reshaping our role responsibilities and career pathways. The goal is to unlock the full potential in each colleague – empowering our people to grow as insurance professionals and add more value to our customers and AIG. How you will create an impact This role may supervise a group of Senior and Associate Underwriters, including designing and monitoring work, development of underwriting and/or marketing...
AIG Chicago, IL Full Time
HUB International
05/18/2026  
Senior Manager, AI Solutions & Automation Delivery
ABOUT US At HUB International, we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence. HUB is a global insurance and employee benefits broker, providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over $5 billion in revenue and almost 20,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions Position Overview HUB is seeking a Senior Manager, AI Solutions &...
HUB International Chicago, IL Full Time
EPIC Insurance Brokers & Consultants
05/15/2026  
Commercial Insurance Client Manager
Come join our team! There are many reasons why EPIC Insurance Brokers & Consultants has become one of the fastest-growing firms in the insurance industry. Fueled and driven by capable, committed people who share common beliefs and values and “bring it” every day, EPIC is always looking for people who have “the right stuff” – people who know what they want and aren’t afraid to make it happen. Headquartered in New York City and founded in 2007, our company has over 3,000 employees nationwide. With locations spread out across the U.S., our local market knowledge and industry expertise helps support our clients' regional and global needs. We have grown very quickly since our founding, and we continue to see growth and success thanks to our hard-working and growth-minded employees.  Our core values are: Owner mindset, Inspire trust, Think big, and Drive results. If these values and growth align with what you're looking for in your next career? Then consider joining...
EPIC Insurance Brokers & Consultants Chicago, IL
Sun Life
05/13/2026  
Health Advisor
Sun Life U.S. is one of the largest providers of employee and government benefits, helping approximately 50 million Americans access the care and coverage they need. Through employers, industry partners and government programs, Sun Life U.S. offers a portfolio of benefits and services, including dental, vision, disability, absence management, life, supplemental health, medical stop-loss insurance, and healthcare navigation. We have more than 6,400 employees and associates in our partner dental practices and operate nationwide. Visit our website to discover how Sun Life is making life brighter for our customers, partners and communities.   Job Description: At Sun Life, we look for optimistic people who want to make life brighter for our Clients. We understand the value of diverse cultures, perspectives, and identities, and want you to bring your full and authentic self to work. Every day, you’ll be empowered and challenged by working with dynamic colleagues...
Sun Life Chicago, IL Full Time
The Hartford
05/08/2026  
National Accounts Risk Engineering Account Executive
Exec Tech Cons Risk Eng - KR07FE We’re determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals – and to help others accomplish theirs, too. Join our team as we help shape the future.              At The Hartford, our Risk Services organization exists to help people and businesses thrive by working directly with customers to assess risk, improve resilience, and deliver practical risk mitigation solutions that make a measurable difference. We partner with customers throughout their lifecycle to identify exposures, reduce losses, and strengthen operational performance—combining consultative expertise, technology enabled risk solutions, and data driven insights to improve outcomes before and after a loss. By integrating risk assessment, prevention, and recovery with the broader insurance experience, we help customers protect what matters most...
The Hartford Chicago, IL Full Time
The Hanover Insurance Group
05/07/2026  
Underwriting Specialist, Technology
For more than 170 years, The Hanover has been committed to delivering on our promises and being there when it matters the most. We live our values every day, demonstrating we  CARE  through our values,  Sustainability  initiatives and  inclusive corporate culture .   Our Technology department is seeking an Underwriting Specialist to join the team in the West Region. This is a Full-time, Exempt role.  POSITION OVERVIEW: Responsible for identifying, soliciting, underwriting and selling new and renewal Technology accounts that drive profitable growth and align with Technology’s appetite and mix goals. Apply technical, sales and analytical skills to provide insurance solutions that help Hanover’s customers manage risk. Demonstrates a thorough understanding of Hanover’s strategies and appetites and will use internal and external data to make appropriate individual and portfolio risk decisions. Serves as a resource and advisor to core underwriters,...
The Hanover Insurance Group Chicago, IL
Voya Financial
05/04/2026  
Compliance Consultant
Together we fight for everyone’s opportunity for a better financial future. We will do this together — with customers, partners and colleagues. We will fight for others, not against: We will stand up for and champion everyone’s access to opportunities. The status quo is not good enough … we believe every individual and every community deserves access to financial opportunities. We are determined to support both individuals and communities in reaching a better financial future.  We know that reaching this future depends on our actions today. Like our Purpose Statement, Voya believes in being bold and committed to action.  We are committed to a work environment where the differences that we are born with — and those we acquire throughout our lives — are understood, valued and intentionally pursued. We believe that our employees own our culture and have a responsibility to foster an environment where we all feel comfortable bringing our whole selves to work. Purposefully...
Voya Financial Chicago, IL Full Time
HUB International
05/04/2026  
Manager, Sales Reporting & Analytics
ABOUT US At HUB International, we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence. HUB is a global insurance and employee benefits broker, providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over $5 billion in revenue and almost 20,000 employees in 600 offices throughout North America, HUB has grown substantially, in part due to our industry leading success in mergers and acquisitions Manager, Sales Reporting & Analytics The Manager, Sales...
HUB International Chicago, IL Full Time
HUB International
04/11/2026  
Senior Vice President, Global Controller
ABOUT US     At   HUB International , we are a team of entrepreneurs. We believe in protecting and supporting the aspirations of individuals, families, and businesses. We help our clients evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees to learn, grow, and make a difference. Our structure enables our teams to   maintain   their own unique, regional culture while   leveraging   support and resources from our corporate centers of excellence.        HUB is   one of the   largest global insurance and employee benefits   broker , providing a boundaryless array of business insurance, employee benefits, risk services, personal insurance, retirement, and private wealth management products and services. With over   $5 billion   in revenue and almost   20,000 employees   in 600 offices throughout North America, HUB has   grown substantially, in   part due to our...
HUB International Chicago, IL Full Time
Huntington
04/07/2026  
Private Bank Market Manager III - Illinois/Wisconsin
Description Summary: The Private Bank Market Manager - Illinois/Wisconsin is responsible for managing and directing all Private Banking sales and service activities for a large region to provide leadership and guidance to Relationship Managers to deepen relationships within the region. Duties and Responsibilities: Establishes strategic plans and marketing initiatives that support business development goals within the market to achieve success across the Private Banking team. Responsible for meeting performance expectations relative to financial objectives for the region. Actively involved in identifying and cultivating relationships with centers of influence and internal leaders across all business segments to meet OCR expectations. May personally manage selected large accounts or portfolios of a complex or sensitive nature. Performs other duties as assigned. Basic Qualifications: Bachelor's...
Huntington Chicago, IL Full Time
HUB International
04/02/2026  
Sr. Risk Consultant, Enterprise Security Risk Management – Business Continuity Management Systems Specialist
ABOUT US At HUB International, we are a team of entrepreneurs. We believe in empowering our clients, and we do so by protecting businesses and individuals in our local communities. We help businesses evaluate their risks and develop solutions tailored to their needs. We believe in empowering our employees. As a global firm, we offer employees resources in both technology and industry expertise, but we still maintain the local flavor of our offices. Our structure enables our teams to maintain their own unique, regional culture while leveraging support and resources from our corporate centers of excellence. HUB is one of the largest global insurance and employee benefits broker, providing a boundaryless array of property, casualty, risk management, life and health, employee benefits, investment and wealth management products and services. With over 20,000 employees in more than 600 offices throughout North America, HUB has grown substantially, in part due to our industry...
HUB International Chicago, IL Full Time
Liberty Mutual
03/25/2026  
Wholesale Management Liability Executive Underwriter
Description     Our Financial Lines Underwriting Team is seeking a highly motivated individual with strong analytical and sales skills to fill an Executive Underwriter opportunity on our Commercial D&O team in Chicago to focus on growing our wholesale brokerage book of business.      This position is a wholesale focused executive underwriter role that will contribute to the growth and profitability of our Private, Not-For-Profit, and Public Directors & Officers, Employment Practices, and Fiduciary Liability product lines through marketing, underwriting, and general product management.  Some risks may require special handling or unusual coverages, including manuscript policy development. The position demonstrates functional technical knowledge of relevant underwriting concepts, practices, procedures, and techniques, to include; coverage issues, multiple product lines, marketing, relevant systems, and competition in the market place. Strong Midwest...
Liberty Mutual Chicago, IL Full Time
Starr Insurance
03/13/2026  
Senior Underwriter
Join Starr, a global leader in commercial insurance with over a century of expertise. We empower our employees to innovate, make impactful decisions, and build lasting client relationships worldwide. At Starr, you'll work in an entrepreneurial culture alongside accessible leaders, leveraging our financial strength and vast industry experience to deliver solutions for our clients, no matter how complex. Grow your career with a rapidly growing company that invests in its people and their ability to drive real progress. Essential Job Functions Analyze and underwrite technical risk exposures on new and renewal business Maintain an existing account renewal book Travel to and conduct client and broker meetings on all major renewals Develop new business account production. Travel to and complete marketing/sales meeting in assigned territories within the Midwest Region Ensure underwriting and service standards are met on assigned accounts Develop insurance proposals, prepare...
Starr Insurance Chicago, IL Full Time
Hiscox
03/04/2026  
Underwriter, Professional Risks
Job Type: Permanent Build a brilliant future with Hiscox   Drive growth with an ambitious team of A&E Underwriters at Hiscox Position: Underwriter Reporting to Regional Manager– A&E Location: Chicago, Los Angeles   The Role: Hiscox USA is currently searching for a dynamic, engaging and solutions-oriented Underwriter to drive new professional liability business and handle complex renewal business within the A&E sector in the Mid-West/West Coast regions. This position provides a unique opportunity for a professional liability generalist or an A&E/construction specialist to join a fast paced, dynamic team to write policies tailored to the specific requirements of the A&E sector. Lines of business include commercial general liability, professional liability (E&O) and cross-sold Cyber from time to time. In addition to insuring architects and engineers, we also specialize in contractors (interior & exterior), real estate...
Hiscox Chicago, IL Full Time
Markel
10/19/2025  
Manager, Business Development - Central Region
What part will you play? If you’re looking for a place where you can make a meaningful difference, you’ve found it. The work we do at Markel gives people the confidence to move forward and seize opportunities, and you’ll find your fit amongst our global community of optimists and problem-solvers. We’re always pushing each other to go further because we believe that when we realize our potential, we can help others reach theirs. Join us and play your part in something special! The Business Development Manager position will be responsible for maintaining and growing Markel's relationships with our retail strategic partners. Your day-to-day duties will include working with underwriters, brokers, Markel leadership, and other key stake holders to profitably grow Markel's book of retail business. The primary geography of the position will be Illinois, Michigan, Ohio, Wisconsin. Total travel will be at least 50%. We are seeking a Business Development Manager for Markel’s Central...
Markel Chicago, IL Full Time

 

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