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Chicago sales leader

65 sales leader jobs found in Chicago

Guardian
10/24/2026  
Regional Sales Leader, Central
Guardian is seeking a Group Benefits Regional Sales Leader in the Chicago market who will be responsible for driving and executing a profitable growth strategy through ongoing sales and retention with brokers. The role will cover groups of 2-2,000 lives with a primary focus down market. The Regional Sales Leader will do this by leading, coaching, and developing a high-performing team. The role will work closely with leadership and internal partners to leverage data when delivering on Guardian’s promise to inspire well-being, managing top and bottom-line growth strategies, and identifying opportunities to increase broker value. Success of this role will be largely dependent on the achievement of financial results, internal and external relationships, and the ability to recruit high potential, early-career talent. You will: Develop a sales plan to achieve corporate, financial, and market goals to maximize profitability, growth, retention, and increased market share....
Guardian Chicago, IL Full Time
Guardian
11/10/2026  
Group Benefits Sales Representative, Premier - Chicago, IL
Position Summary : Guardian is seeking a Group Benefits Sales Representative to build and deepen relationships with leading brokers, consultants, and clients while driving profitable new business and retention in the large-market segment. You will bring Guardian's full portfolio of benefits and technology-enabled solutions to market, translate complex client needs into differentiated strategies, and serve as a trusted resource throughout the sales lifecycle. Success requires disciplined territory and pipeline management, strong cross-functional partnership, and a consistent focus on the broker and client experience. This role reports to the Market Leader for the assigned territory.  You are : A consultative, externally focused sales leader who earns credibility with sophisticated brokers, consulting houses, and large employers.  A strategic relationship builder who combines market insight, executive presence, and disciplined follow-through to create...
Guardian Chicago, IL Full Time
Guardian
11/04/2026  
Group Benefits Market Leader, Central Region
Position Summary: Guardian is seeking a Group Benefits Market Leader for our Central Region to develop and execute a profitable growth strategy across the assigned market, with responsibility for new sales, retention, and broker relationships supporting groups of 2 to 2,000 lives and a primary focus on the 100 to 1,999 segments. You will lead, coach, and develop a high-performing sales team while building strong relationships with Guardian’s highest-value and fastest-growing brokers and distribution partners. Working across Underwriting, Client Management, Product, Finance, and other partners, you will use market intelligence, data, analytics, and AI-enabled tools to identify opportunities, improve decisions, and deliver top- and bottom-line results. Success requires disciplined execution, inclusive people leadership, sound judgment, and the ability to strengthen Guardian’s presence and value in the market.   You are: A strategic, hands-on sales leader who translates...
Guardian Chicago, IL Full Time
CCC Intelligent Solutions
10/30/2026  
Vice President, Insurance Software Sales
Salary range is: $217,236.65 - $225,000.00 This position is long-term incentive and bonus and/or commission eligible. CCC Intelligent Solutions Inc. (CCC) is a leading cloud platform for the multi-trillion-dollar insurance economy , creating intelligent experiences for insurers, repairers, automakers, part suppliers, and more. At CCC, we’re making life just work by empowering more than 35,000 businesses with industry-leading technology to get drivers back on the road and to health quickly and seamlessly. We’re pushing boundaries with innovative AI solutions that simplify and enhance the claims and repair journey. Through purposeful innovation and the strength of its connections, CCC technologies empower the people and industry relied upon to keep lives moving forward when it matters most. Learn more about CCC at www.cccis.com .   The Role We are seeking a proven sales leader to accelerate the adoption, expansion, and commercial success of our Automobile Physical...
CCC Intelligent Solutions Chicago, IL Full Time
Acrisure
10/31/2026  
Demand Generation Manager
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.   Job Summary Acrisure is seeking a Demand Generation Manager to develop and execute marketing campaigns that drive engagement, accelerate pipeline, and support revenue growth. This role is responsible for creating multi-channel campaigns end to end from...
Acrisure Chicago, IL
CCC Intelligent Solutions
09/18/2026  
Director, GTM Enablement
Salary range is: $157,417.86 - $185,000.00 This position is long-term incentive and bonus and/or commission eligible. CCC Intelligent Solutions Inc. (CCC) is a leading cloud platform for the multi-trillion-dollar insurance economy , creating intelligent experiences for insurers, repairers, automakers, part suppliers, and more. At CCC, we’re making life just work by empowering more than 35,000 businesses with industry-leading technology to get drivers back on the road and to health quickly and seamlessly. We’re pushing boundaries with innovative AI solutions that simplify and enhance the claims and repair journey. Through purposeful innovation and the strength of its connections, CCC technologies empower the people and industry relied upon to keep lives moving forward when it matters most. Learn more about CCC at www.cccis.com .   The Role The Director, GTM Enablement, leads the centralized GTM Enablement COE responsible for improving seller readiness, execution...
CCC Intelligent Solutions Chicago, IL Full Time
Applied Systems
10/20/2026  
Sr. Technical Consultant
Job Description   Team:  CX Solution Services Salary Range: $105,000 - $130,000 USD Location: Remote   Opportunity for Impact Applied is where insurance technology gets reinvented, and we build it fast. Our cloud software and AI-powered solutions reach thousands of agencies and brokers worldwide, setting the pace for what modern insurance can do.   We’re looking for a Sr Technical Consultant to join our CX Solution Services team and lead the architecture, integration, and cloud delivery standards across our consulting practice, advising client CIOs and CTOs on their most complex digital transformations.   What You’ll Do Define and govern architecture, integration, and cloud delivery standards across Applied’s software ecosystem, including technical strategy with partners such as Google Cloud Platform Act as the executive technical authority on our largest, highest-stakes enterprise implementations, operating with full...
Applied Systems Chicago, IL
Core Specialty
11/12/2026  
Commercial Surety Regional Manager
- The Commercial Surety Regional Manager is responsible for the underwriting, marketing, production, profitability, and overall management of a regional Commercial Surety portfolio. This position serves as the senior underwriting leader for the assigned territory and is accountable for achieving premium growth, underwriting profitability, agency development, and portfolio management objectives. The Regional Manager will develop and maintain strong relationships with agents, brokers, principals, indemnitors, and other business partners while exercising significant underwriting authority and ensuring compliance with company underwriting guidelines and risk appetite. The position is highly market-facing and focused on profitable business development, agency management, and underwriting execution. Key Accountabilities/Deliverables: Underwriting Leadership Serve as lead underwriter for the assigned territory. Analyze, evaluate, and approve commercial surety...
Core Specialty Chicago, IL Full Time
Ryan Specialty
11/12/2026  
Brokerage Operations Intern
RT Specialty, a division of Ryan Specialty, is a leading wholesale distributor of specialty insurance products and services. Our experienced brokers are specialized in property, casualty, professional lines, transportation and workers’ compensation, providing creative solutions to retail brokerage firms. We define ourselves through our superior execution on behalf of our clients, which has established us as a leader in the industry. Position Summary Ryan Specialty is seeking motivated students to join our Summer 2027 Brokerage Operations Internship, 8-10 weeks, 5 days in office, paid internship designed to provide hands-on exposure to specialty insurance brokerage operations. *The hourly pay rate for this internship is $22/ hour.* Interns will work alongside brokerage professionals, gain insight into client service and operational processes, and develop foundational skills for a career in insurance and risk management. The opportunity is open to candidates based in the...
Ryan Specialty Chicago, IL Full Time
WTW
11/12/2026  
Construction - Senior Client Advocate
The Senior Client Advocate provides strategic relationship management and placement, taking advantage of our specialized Construction industry experience and unparalleled market know-how, to craft strategies for clients to quantify, mitigate, and transfer risk. This position will also create strategies and execute the placement of Builders Risk, Property and Casualty lines of business for both primary and excess policies. If you are client-centric, interested in affiliating with an industry leader, and committed to helping clients unlock their potential through effective risk management strategies, this may be the perfect opportunity for you!   The Role The Senior Client Advocate is responsible for providing strategic relationship management, placement of Builders Risk , Property and  casualty lines, and consultative services to our clients. The Senior Client Advocate is responsible for marshaling Willis Towers Watson resources to provide coordinated service and placement...
WTW Chicago, IL Full Time
Acrisure
11/11/2026  
Life & Disability Client Advisor
Job Description Job Title: Sales Manager Agency/Platform: Wholesure, Life & Disability Practice Reporting to: Vice President, Sales Location: Multiple Potential Locations About Acrisure: Acrisure is a global Fintech leader that combines the best of humans and high tech to offer multiple financial products and services to millions of businesses and individual clients. We connect clients to solutions that help them protect and grow what matters, including Insurance, Reinsurance, Cyber Services, Mortgage Origination and more. Acrisure employs over 17,000 entrepreneurial colleagues in 21 countries and have grown from $38 million to $4.3 billion in revenue in just over ten years. Our culture is defined by our entrepreneurial spirit and all that comes with it: innovation, client centricity and an indomitable will to win. Summary: The Sales Manager is a dynamic and pivotal role in driving the company’s growth and maintaining client...
Acrisure Chicago, IL Full Time
Nationwide
11/10/2026  
Director, Business Development - Surety (Large Commercial)
If you’re passionate about helping people protect what matters most to them at a Fortune 100 company with nearly $70 billion in annual sales, as well as innovating and simplifying processes and operations to provide the best customer value, then Nationwide’s Property and Casualty team could be the place for you! At Nationwide®, “on your side” goes beyond just words. Our customers and partners are at the center of everything we do and we’re looking for associates who are passionate about delivering extraordinary care. Areas of focus for this role: I dentifying expansion opportunities within the territory by partnering with brokers on new business development, producer planning, and target account strategies. Contributing to territory-level business planning by tracking production, visibility, and marketing trends and activities Supporting the negotiation and execution of indemnity, collateral, and other risk-mitigation arrangements on larger or more complex accounts...
Nationwide Chicago, IL Full Time
Nationwide
11/06/2026  
Underwriting Specialist - Management Liability D&O (Financial Institutions)
If you’re passionate about helping people protect what matters most to them at a Fortune 100 company with nearly $70 billion in annual sales, as well as innovating and simplifying processes and operations to provide the best customer value, then Nationwide’s Property and Casualty team could be the place for you! At Nationwide®, “on your side” goes beyond just words. Our customers and partners are at the center of everything we do and we’re looking for associates who are passionate about delivering extraordinary care. *This role does not qualify for employer-sponsored work authorization. Nationwide does not participate in the Stem OPT Extension program.* #LI-CL1 Job Description Summary Are you a critical thinker who can analyze complex risk and find insurance solutions that balance customer needs with business goals? If you can take initiative, use both your analytical and creative abilities to make sound decisions and have a desire to help people solve real challenges,...
Nationwide Chicago, IL Full Time
Pet Partners Pet Insurance
11/06/2026  
Senior Director, Technology Delivery & Strategy
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.  Job Summary: The Senior Director will lead a multi-brand business unit to drive consolidated roadmaps, tracking, budget, and delivery of all technology projects. This role will work closely with senior leadership to: Align technology execution to business outcomes Driving roadmaps including moving...
Pet Partners Pet Insurance Chicago, IL Full Time
Independence Pet Group
11/06/2026  
Senior Director, Technology Delivery & Strategy
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.  Job Summary: The Senior Director will lead a multi-brand business unit to drive consolidated roadmaps, tracking, budget, and delivery of all technology projects. This role will work closely with senior leadership to: Align technology execution to business outcomes Driving roadmaps including moving...
Independence Pet Group Chicago, IL Full Time
AIG
11/04/2026  
Regional Production Specialist Sr, Excess & Surplus Lines
At AIG, we are reimagining the way we help customers to manage risk. Join us as a Regional Production Specialist Sr, Excess & Surplus Lines 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 Underwriting AIG Underwriting teams help to find insurance solutions in areas including Financial Lines, Property, Casualty, Specialty Lines, Cyber, and Multinational Clients. 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 Senior Regional Production Specialist must be able to illustrate the highest levels of technical proficiency and underwriting acumen combined with marketing and sales...
AIG Chicago, IL Full Time
WTW
10/31/2026  
Chicago Health & Benefits Office Business Leader
Summary of Role  The Chicago Health & Benefits (H&B) OBL is a key member of the Midwest Region H&B leadership team. In this role, you will have ultimate accountability for the H&B business and team in the market: the role’s success metrics are tied to growing revenue and talent. This includes revenue growth, direct expense management, and profitability; colleague attraction, development and engagement; and client and colleague retention. The OBL is effectively the Growth Leader of the market, responsible for building and executing the growth plan to meet/exceed the expected results. The OBL will be responsible for building the WTW brand externally, and leading key new client pursuits The role will report to the Health & Benefits Midwest Region Leader (RL). The Role Build and execute the local market business strategy to achieve growth, retention, staffing, and profitability goals. Manage the local H&B new-business pipeline and...
WTW Chicago, IL Full Time
Acrisure
10/31/2026  
Content Strategist
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.   Job Summary Acrisure is seeking a Content Strategist to develop and execute a content strategy that supports demand generation across the stages of the buying journey for a growing portfolio. This role turns messaging and positioning into scalable,...
Acrisure Chicago, IL Full Time
Acrisure
10/31/2026  
Content Marketing & Innovation Manager
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.   Job Summary Acrisure is seeking a Content Marketing Manager, Content Innovation to shape how buyers understand their challenges, evaluate solutions, and experience the value of Acrisure in the market. As the lead content marketer for a designated portfolio of...
Acrisure Chicago, IL Full Time
Acrisure
10/31/2026  
Senior Integrated Marketing Manager
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.   Job Summary Acrisure is seeking a Senior Integrated Marketing Manager to define the buyer journeys, develop campaign strategies, and create integrated marketing plans that communicate and demonstrate the value of a growing product portfolio. This role is...
Acrisure Chicago, IL Full Time

 

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