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Full Time 37
Chicago mid market director Illinois

56 mid market director jobs found in 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
Hiscox
06/18/2026  
AVP, Team Manager
Job Type: Permanent Build a brilliant future with Hiscox   About Hiscox USA: Hiscox USA underwrites small- to mid-market commercial risks through brokers, other insurers and distribution partners and directly to businesses. In 2023, gross written premiums for the segment will represent over $1bn. Approximately 50% of the portfolio comprises small commercial business sold either online or through intermediaries, and the remaining 50% represents traditionally traded business intermediated through broking partners for Property and Casualty and Specialty Lines, including Professional Liability, Cyber, Technology and Media & Entertainment. Hiscox USA has built the digital business through ongoing investment in the brand, technology and operational capabilities. The business has pursued an omni-channel approach from its inception and is less constrained by the channel conflict that affects some competitors. Customers have a choice of buying policies online end-to-end, by...
Hiscox Chicago, IL Full Time
Hiscox
05/29/2026  
AVP, Team Manager
Job Type: Permanent Build a brilliant future with Hiscox   Position: AVP, Team Manager – GL BI and PD Reporting to: Claims Director, Property & Casualty         Band: II Location: Atlanta, Boston, Chicago, Hartford, New York, Scottsdale Flexibility: Permanent Travel: Hybrid   About Hiscox USA: Hiscox USA underwrites small- to mid-market commercial risks through brokers, other insurers and distribution partners and directly to businesses. In 2023, gross written premiums for the segment will represent over $1bn. Approximately 50% of the portfolio comprises small commercial business sold either online or through intermediaries, and the remaining 50% represents traditionally traded business intermediated through broking partners for Property and Casualty and Specialty Lines, including Professional Liability, Cyber, Technology and Media & Entertainment. Hiscox USA has built the digital business through ongoing investment in the brand, technology...
Hiscox Chicago, IL Full Time
At-Bay
02/22/2026  
Senior Actuarial Analyst, Pricing
Senior Actuarial Analyst DRIVE PROFITABLE GROWTH FOR THE BUSINESS About At-Bay   At-Bay is the world’s first InsurSec provider designed from the ground up to help businesses tackle cyber risk head on. By combining industry-leading insurance with world-class cybersecurity technology, At-Bay offers end-to-end prevention and protection for the digital age. With 98% of cyber insurance claims in the past five years coming from small and mid-size businesses with revenue under $2B, providing an integrated solution to help manage risk is more critical than ever. At-Bay helps its 35,000+ customers close their security technology and skills gap — all through their cyber insurance policy — making them less likely to be hit with a ransomware attack. As a full-stack insurance company, At-Bay offers multiple lines of specialty insurance, including Cyber, Tech E&O, and Miscellaneous Professional Liability (MPL) policies. Why you should join our Actuarial Pricing...
At-Bay Chicago, IL
At-Bay
02/19/2026  
Actuarial Manager, Pricing
Actuarial Manager, Pricing DRIVE PROFITABLE GROWTH FOR THE BUSINESS About At-Bay   At-Bay is the world’s first InsurSec provider designed from the ground up to help businesses tackle cyber risk head on. By combining industry-leading insurance with world-class cybersecurity technology, At-Bay offers end-to-end prevention and protection for the digital age. With 98% of cyber insurance claims in the past five years coming from small and mid-size businesses with revenue under $2B, providing an integrated solution to help manage risk is more critical than ever. At-Bay helps its 40,000+ customers close their security technology and skills gap — all through their cyber insurance policy — making them less likely to be hit with a ransomware attack. As a full-stack insurance company, At-Bay offers multiple lines of specialty insurance, including Cyber, Tech E&O, and Miscellaneous Professional Liability (MPL) policies. Your Impact As an Actuarial Manager on the...
At-Bay Chicago, IL
At-Bay
02/19/2026  
Actuary / Senior Actuary
  Actuary / Senior Actuary, Pricing DRIVE PROFITABLE GROWTH FOR THE BUSINESS About At-Bay   At-Bay is the world’s first InsurSec provider designed from the ground up to help businesses tackle cyber risk head on. By combining industry-leading insurance with world-class cybersecurity technology, At-Bay offers end-to-end prevention and protection for the digital age. With 98% of cyber insurance claims in the past five years coming from small and mid-size businesses with revenue under $2B, providing an integrated solution to help manage risk is more critical than ever. At-Bay helps its 35,000+ customers close their security technology and skills gap — all through their cyber insurance policy — making them less likely to be hit with a ransomware attack. As a full-stack insurance company, At-Bay offers multiple lines of specialty insurance, including Cyber, Tech E&O, and Miscellaneous Professional Liability (MPL) policies. Why you should join our  Actuarial...
At-Bay Chicago, IL
Hiscox
07/09/2026  
Senior Underwriter, Professional Risks
Job Type: Permanent Build a brilliant future with Hiscox   Drive growth with an ambitious team of MPL Underwriters at Hiscox Position: Sr. Underwriter Reporting to Regional Manager – MPL The Role: Hiscox USA is currently searching for a dynamic, engaging and solutions-oriented Sr. Underwriter to drive new professional liability business and complex renewal business within the MPL sector in the West Coast region. This position provides a unique opportunity for a professional liability specialist to join a fast paced, dynamic team to write policies tailored to the specific requirements of the MPL sector. Lines of business include commercial general liability, professional liability (E&O) and cross-sold Cyber from time to time. We also specialize in accountants, real estate agents, property managers, trustees, consultants, freight forwarders, staffing firms, TPAs, associations, and more! Risks vary greatly in size and complexity (from start-ups to...
Hiscox Chicago, IL Full Time
QBE
07/09/2026  
Senior Actuarial Analyst II
Primary Details Time Type: Full time Worker Type: Employee Title: Senior Analyst II - Actuarial The Opportunity: In this role you will proactively provide actuarial reserving services and leadership within various commercial, specialty and legacy lines by demonstrating technical competence in a variety of actuarial/statistical concepts, practices and procedures while taking the lead in defining project scope, key issues, timeframes, and analytical approaches and priorities with a large degree of creativity and self-direction. • Location: Sun Prairie, Wisconsin or Atlanta, GA or New York, New York, or Chicago, IL • Work Arrangement: QBE requires employees to work in office 8-12 days a month • The salary range for this role is:  Sun Prairie, Wisconsin ($98,500 - $147,500)  Atlanta, GA ($98,500 - $147,500)  New York, New York ($123,000 - $184,500)  Chicago, IL ($108,500 - $162,500) Your new role Focus primarily on reserving for various commercial, specialty...
QBE Chicago, IL Full Time
Applied Systems
07/08/2026  
Associate Customer Success Manager
Job Description Amazing Career Moments Happen Here    Transforming the insurance industry is ambitious, we know. That’s why at Applied, we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the Insurtech game, we’re not just redefining what’s achievable, we’re creating a place where amazing career moments are made possible.      Position Overview    We’re seeking an Associate Customer Success Manager to join our Customer Success team in a remote capacity within the United States, with preference given to candidates located in the Chicago, Dallas, and Atlanta areas. The ideal candidate is an early-career professional who is eager to learn, build customer relationships, and grow within Customer...
Applied Systems Chicago, IL
Applied Systems
07/08/2026  
Manager, Services Advisors
Job Description   Amazing Career Moments Happen Here    Transforming the insurance industry is ambitious, we know. That’s why at Applied, we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the Insurtech game, we’re not just redefining what’s achievable, we’re creating a place where amazing career moments are made possible.      Position Overview    We’re searching for a Manager, Services Advisors to join our CX Services team — a predominantly remote (or hybrid if preferred) role for someone residing near either our Chicago, Atlanta or Dallas offices.   Reporting within the CX Services organization, this leader manages a team of Services Advisors who scope the training, consulting, and technical...
Applied Systems Chicago, IL
PURE Insurance
07/07/2026  
State Management Product Analyst
About the role.  The State Management Product Analyst is an entry level member of the Product Management team and will be based out of our Chicago, IL or White Plains, NY office. We are seeking an intelligent, data-minded individual with strong quantitative and analytic skills to assist in the successful implementation of high net worth property and casualty (P&C) insurance products and rates in support of our sustainable growth objectives.   What you’ll do. Support the execution of sustainable growth strategies in states by implementing, maintaining and monitoring the respective P&C insurance products.  Execute rate reviews and workflows with guidance that achieve target growth and underwriting margin objectives with a focus on member experience.  This includes learning to develop rate proposals, state filings for regulatory support, technology specifications, and internal and external communications for all rate and product filings with direction....
PURE Insurance Chicago, IL Full Time
Applied Systems
07/07/2026  
Sr. Business Insights Analyst
Job Description   Amazing Career Moments Happen Here    Transforming the insurance industry is ambitious, we know. That’s why at Applied, we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the Insurtech game, we’re not just redefining what’s achievable, we’re creating a place where amazing career moments are made possible.      Position Overview    We’re searching for a Senior Business Insights Analyst to join our Business Operations team in a hybrid work location from our Chicago office. In this role, you will primarily focus on partnering with stakeholders in our CX organization to analyze data from across our customer experience organization, build reporting infrastructure, and surface insights...
Applied Systems Chicago, IL
HUB International
07/06/2026  
Assistant Vice President - Executive Liability
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 environment...
HUB International Chicago, IL Full Time
HUB International
07/04/2026  
Security Support Manager
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 Job Description The Security Support Manager leads a team of...
HUB International Chicago, IL Full Time
CNA
07/02/2026  
AVP, Claims Client Services
You have a clear vision of where your career can go. And we have the leadership to help you get there.  At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential.  Officer-level leader responsible for the strategic direction, leadership, and performance of CNA’s Client Services organization, ensuring the delivery of a consistent, differentiated claims experience across enterprise product lines and business segments. Leads a national team of client-facing professionals who serve as trusted advisors to customers, underwriting partners, and distribution partners, driving service excellence, client retention, and profitable growth. Develops and maintains strong executive-level relationships with key distribution partners, brokers, and agencies across the country, serving as a visible ambassador for CNA Claims and a critical contributor to market...
CNA Chicago, IL Full Time
AIG
07/01/2026  
Executive Underwriter, AIGRM
At AIG, we are reimagining the way we help customers to manage risk. Join us as an Executive Underwriter, AIG Risk Management (AIGRM) 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 you mark in Underwriting 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 The Executive Underwriter will be responsible for underwriting the Workers’ Compensation, General Liability and Auto Liability primary Casualty product lines...
AIG Chicago, IL Full Time
Applied Systems
06/30/2026  
Associate Customer Support Technician
Job Description Amazing Career Moments Happen Here    Transforming the insurance industry is ambitious, we know. That’s why at Applied, we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the Insurtech game, we’re not just redefining what’s achievable, we’re creating a place where amazing career moments are made possible.      Position Overview    We’re searching for an Associate Customer Support Technician to join our outstanding Support team in this remote work opportunity based in the United States. In this position, you will assist our customers with any questions or problems they may have regarding software, hardware, or any other products purchased from our company.  You will provide...
Applied Systems Chicago, IL
Applied Systems
06/30/2026  
Associate Customer Project Lead
Job Description Amazing Career Moments Happen Here Transforming the insurance industry is ambitious, we know. That’s why at Applied, we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the Insurtech game, we’re not only redefining what’s achievable, we’re also creating a place where amazing career moments are made possible.   Position Overview We’re searching for two Associate Customer Project Leads to join our Implementation Team in a remote capacity within the United States. To keep us headed in the right direction, we’re looking for people who understand winning is a team sport, who value and seek to learn from our team’s diverse experiences and backgrounds, who welcome a challenge and take...
Applied Systems Chicago, IL
Applied Systems
06/27/2026  
AI Enablement Professional Services Lead
Job Description   Amazing Career Moments Happen Here     Transforming the insurance industry is ambitious, we know. That’s why at Applied, we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the Insurtech game, we’re not just redefining what’s achievable; we’re creating a place where amazing career moments are made possible.        Position Overview    We’re searching for a AI Enablement Services Lead to join our Professional Services team (Implementation, PMO, Data, Customer Success) in a hybrid location from our Chicago office. As the AI Enablement Services Lead, you will be the architect of the "Next-Gen Professional Services" organization. You are responsible for identifying, building, and...
Applied Systems Chicago, IL
Applied Systems
06/27/2026  
Director, Product Marketing - Agency
Job Description Amazing Career Moments Happen Here       Transforming the insurance industry is ambitious, we know. That’s why at Applied, we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the Insurtech game, we’re not just redefining what’s achievable; we’re creating a place where amazing career moments are made possible.        Position Overview      We're hiring a Director, Product Marketing — Agency for a hybrid role (1-2 days a week in-office) with occasional travel, leading product marketing strategy and execution for the largest buyer segment in Applied's portfolio. This role owns positioning, GTM, and team leadership for the Applied Epic ecosystem and EZLynx, partnering closely with...
Applied Systems Chicago, IL

 

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