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Full Time 48
Chicago benefits advisor lead Illinois

54 benefits advisor lead jobs found in Chicago, IL

WTW
05/12/2026  
Director, Digital Advisory Solutions Seller
The Role This role sits within the Work & Rewards business and focuses on understanding customer needs and pain points to demonstrate the value and benefits of our advisory products and solutions. This role is pivotal in bridging the gap between our clients, advisory consultants, and internal product teams. It plays a critical role in the sales process by delivering compelling, customized product demonstrations and translating complex technical capabilities into clear business value that meets customer- specific requirements.  The Responsibilities Solution Design & Communication ​ Translate complex compensation and HR technology capabilities into clear, compelling business value propositions. ​ Collaborate with internal teams to design and present solutions that meet client requirements and strategic goals. ​ Cross-Functional Collaboration ​ Serve as a liaison between clients, advisory consultants, product development/ enhancement/...
WTW Chicago, IL Full Time
CNA
05/10/2026  
Strategic Sourcing Managing Director
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.  Serves as a people leader responsible for identifying, designing, and implementing third-party vendor solutions that enable Claims strategy and operational excellence. Acts as a trusted advisor to Claims leadership, proactively bringing forward innovative solutions, emerging capabilities, and market insights that enhance customer outcomes, improve efficiency, and drive competitive advantage. Partners closely with business leaders across all phases of sourcing and contracting from project planning through execution ensuring alignment to strategic priorities. A key focus area includes category strategy development and execution, incorporating a deep understanding of Claims business objectives...
CNA Chicago, IL Full Time
HUB International
05/10/2026  
Senior Change 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 OVERVIEW As a member of the Change Enablement team within the...
HUB International Chicago, IL Full Time
Liberty Mutual
05/08/2026  
Personal Lines Senior Territory Manager - Independent Agency Distribution
Description Liberty Mutual Insurance is a leading global insurer committed to helping people live safer, more secure lives. Within our Personal Lines business, we partner with independent agents across the United States to deliver a broad portfolio of property and casualty solutions. We value a diverse, inclusive workforce and offer meaningful work where your expertise directly impacts growth, customer experience, and the communities we serve.   As a Senior Territory Manager, you will drive profitable premium growth across an assigned territory by building strong, consultative partnerships with independent agents. This role is critical to expanding market share through strategic agency management, collaboration with underwriting and internal partners, and disciplined execution of Personal Lines growth initiatives.   Key Responsibilities   Own and manage an assigned territory, driving profitable growth in alignment with financial and operational...
Liberty Mutual 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
Ascot Group
05/07/2026  
Director, HR Business Partner
This is an opportunity to join Ascot Group - one of the world’s preeminent specialty risk underwriting organizations.   Designed as a modern-era company operating through an ecosystem of interconnected global operating platforms, we’re bound by a common mission and purpose. Our greatest strength is a talented team who flourish in a collaborative, inclusive, and entrepreneurial culture, steeped in underwriting excellence, integrity, and a passion to find a better way, The Ascot Way .   The Ascot Way guides our people and our organization. Our underwriting platforms collaborate to find creative ways to deploy our capital in a true cross-product and cross-platform approach. These platforms work as one, deploying our capital creatively through our Client Centric, Risk Centric and Technology Centric strategies   Built to be resilient, Ascot offers clients leading financial security while delivering bespoke products and world class service — both pre- and post-claims. Ascot...
Ascot Group 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
Independence Pet Group
05/03/2026  
Director, Change Management
Established in 2021,   Independence Pet Holdings   is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.   We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands.  Independence Pet Holdings (IPH) is seeking a collaborative, results‑driven Change Management Director to play a critical role in enabling successful adoption of enterprise transformation initiatives. This role will partner closely with Senior Transformation Program Business Owners, Program Managers, and...
Independence Pet Group Chicago, IL Full Time
Pet Partners Pet Insurance
05/03/2026  
Director, Change Management
Established in 2021,   Independence Pet Holdings   is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.   We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands.  Independence Pet Holdings (IPH) is seeking a collaborative, results‑driven Change Management Director to play a critical role in enabling successful adoption of enterprise transformation initiatives. This role will partner closely with Senior Transformation Program Business Owners, Program Managers, and...
Pet Partners Pet Insurance Chicago, IL Full Time
Independence Pet Group
04/28/2026  
Sr. Project Manager
Established in 2021,   Independence Pet Holdings   is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.   We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands.  Pets Best ,   a subsidiary of IPH , offers pet insurance and wellness plans for dogs and cats in every state. Founded in 2005 with a mission to provide access to comprehensive animal healthcare at an affordable price, Pets Best delivers flexible coverage, an easy claims process, and excellent...
Independence Pet Group Chicago, IL Full Time
Pet Partners Pet Insurance
04/28/2026  
Sr. Project Manager
Established in 2021,   Independence Pet Holdings   is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.   We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands.  Pets Best ,   a subsidiary of IPH , offers pet insurance and wellness plans for dogs and cats in every state. Founded in 2005 with a mission to provide access to comprehensive animal healthcare at an affordable price, Pets Best delivers flexible coverage, an easy claims process, and excellent...
Pet Partners Pet Insurance Chicago, IL Full Time
Liberty Mutual
04/21/2026  
Technical Director
Description Position Summary We are seeking a Technical Director in a highly visible role for one of our largest accounts. This position serves as a primary technical advisor and strategic partner to the customer, partnering directly with their Global Health & Safety leaders to identify, quantify, reduce, and eliminate risk across complex logistics operations. The role is central to advancing the Crash Prevention Strategy. This position is work from home, due to the dedicated aspect of the account, but does require up to 30% overnight travel to various customer locations across the U.S. and possible internationally. Position may require occasional early morning, evening, or weekend support based on operational needs. Strategic Impact As a senior technical leader, the Technical Director shapes long-term safety strategy, translates emerging science and technology into actionable solutions, and ensures alignment with Liberty Mutual’s leadership...
Liberty Mutual Chicago, IL Full Time
PURE Insurance
04/14/2026  
VP, Head of Actuarial Pricing
About the role: We are seeking a highly experienced and strategic VP, Head Pricing Actuary to lead and modernize our pricing function. This role is responsible for setting the enterprise pricing vision, advancing technical capabilities, and ensuring pricing is a key driver of sustainable growth. The ideal candidate brings deep expertise in P&C pricing, particularly in personal lines, combined with a proven ability to lead high-performing teams and transform legacy pricing approaches into a sophisticated, data-driven, and technology-enabled function. This individual will operate as a senior leader, influencing business strategy and elevating pricing as a core competitive advantage. What you'll do: Strategic Leadership Define and execute the enterprise pricing strategy, aligning with business objectives for growth, profitability, and risk selection Lead, develop, and scale a high-performing pricing team, building strong technical and leadership...
PURE Insurance Chicago, IL Full Time
CNA
03/19/2026  
AVP, Senior Principal Enterprise Architect - Data
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.  Job Summary The AVP, Senior Principal Enterprise Architect - Data is CNA’s most senior individual contributor, providing architectural leadership across complex portfolios or domain disciplines. This role connects enterprise strategy with execution, drives cross-portfolio integration, and ensures architectural alignment and reuse. The AVP, Senior Principal Enterprise Architect - Data shapes domain-level strategy, leads complex architectural initiatives, and mentor other architects to elevate architectural maturity and enterprise-wide impact. This specific role will be aligned to the Data Portfolio with a focus on aligning across our delivery value streams and driving a “Build with a Data...
CNA Chicago, IL Full Time
Acrisure
03/15/2026  
Client Advisor
Job Description About Acrisure: A global fintech leader, Acrisure empowers millions of ambitious businesses and individuals with the right solutions to grow boldly forward. Bringing cutting-edge technology and top-tier human support together, we connect clients with customized solutions across a range of insurance, reinsurance, payroll, benefits, cybersecurity, mortgage services – and more.    In the last twelve years, Acrisure has grown in revenue from $38 million to almost $5 billion and employs over 19,000 colleagues in more than 20 countries. Acrisure was built on entrepreneurial spirit. Prioritizing leadership, accountability, and collaboration, we equip our teams to work at the highest levels possible.  *This position is location-flexible; the cities listed are primary target cities. Applicants from additional locations will be considered. Job Summary The Sales Manager is a dynamic and pivotal role in driving the company’s growth and maintaining client...
Acrisure Chicago, IL
Brown & Brown
03/01/2026  
Senior Benefits Consultant
Built on meritocracy, our unique company culture rewards self-starters and those who are committed to doing what is best for our customers. Brown & Brown is seeking a Senior Benefits Consultant to join our growing team! This role blends thought leadership, market strategy, and high‑impact consulting for the purpose of developing new business. You will shape benefits strategies for major employers while driving new business, expanding relationships, and positioning our firm as a trusted advisor in a competitive marketplace. How You Will Contribute:   Strategic Advisory Serve as the lead strategic advisor for large and mid-sized employers, developing multi‑year health & welfare benefits strategies that improve cost, quality, and employee experience. Guide C‑suite leaders on long‑term healthcare strategies and tactics. Provide insights on emerging market trends, regulatory changes, and innovation within benefits, helping clients stay ahead of...
Brown & Brown Chicago, IL Full Time
Acrisure
03/01/2026  
Payroll Client Advisor
Job Description About Auris Auris is the payroll and HR partner built for small and medium-sized business who can’t afford to get it wrong. Trusted by over 50,000 business nationwide, Auris pairs easy-to-use technology with real human services to give leaders the confidence that every detail is done right - so they can focus on growing their team and their business. Acquired by Acrisure in 2025, Auris formerly Heartland Payroll is accelerating its vision to deliver seamless human-centered technology to help small businesses thrive. Job Summary Responsible for prospecting and running Auris Payroll presentations both in person and over the phone to small and mid-sized merchants and businesses to ultimately close deals within a fast sales cycle. As a Payroll Client Advisor you will report to a Payroll Division Manager and receive coaching from a Territory Manager. Activities include explaining our value proposition to clients via Atlas CRM, upselling current clients...
Acrisure Chicago, IL
Acrisure
03/01/2026  
Payroll Territory Manager
Job Description About Auris Auris is the payroll and HR partner built for small and medium-sized business who can’t afford to get it wrong. Trusted by over 50,000 business nationwide, Auris pairs easy-to-use technology with real human services to give leaders the confidence that every detail is done right - so they can focus on growing their team and their business. Acquired by Acrisure in 2025, Auris formerly Heartland Payroll is accelerating its vision to deliver seamless human-centered technology to help small businesses thrive. Job Summary Responsible for prospecting and running Auris Payroll presentations both in person and over the phone to small and mid-sized merchants and businesses to ultimately close deals within a fast sales cycle. As a Payroll Territory Manager (PTM), you will report to the Payroll Division Manager (PDM).  Activities include explaining our value proposition to clients via Atlas CRM, upselling current clients on other Auris products and...
Acrisure Chicago, IL
CNA
02/25/2026  
Senior Actuarial Consultant - Reserving (P&C Healthcare)
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.  As a member of CNA’s Actuarial organization, you will be part of a community that provides deep specialization and discipline as trusted advisors, unlocks data to enable business partners to advance our global market strategy, and drives business solutions through actionable analytics and insights. Consider an actuarial opportunity on CNA's Healthcare Reserving team. In this position, you will develop and recommend actuarial reserve strategies of a complex nature for CNA’s Healthcare medical malpractice and Surety books of business. You will collaborate with business partners at all levels and Actuarial senior leaders. You will serve as a trusted advisor to provide actuarial analyses and...
CNA Chicago, IL Full Time
WTW
02/24/2026  
Director, Health and Benefits, Client Service Team
As a Health and Benefits Director, you will lead client engagements involving the design and management of the full array of health and benefits programs.  You will drive the strategy and grow relationships with current clients by leveraging your expertise alongside WTW’s array of solutions and capabilities and will generate new business by participating in prospecting activities.  You will have the opportunity to provide input into the evolution of the WTW Health and Benefits practice and to be a leader in the marketplace. Note: Employment-based non-immigrant visa sponsorship and/or assistance is not offered for this specific job opportunity. The Role Serve as the strategic partner and trusted advisor to clients in the design and management of their health and benefits programs.  Responsibilities include: Leading the client service team in the design and delivery of project plans; ensuring progress against established objectives, budgets, timelines, deliverables and...
WTW Chicago, IL Full Time

 

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