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Chicago regional sales director

19 regional sales director jobs found in Chicago

Nationwide
10/21/2026  
Executive Underwriting Director, Brokerage Excess
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. Lead the future of specialty insurance as our Executive Underwriting Director in Brokerage Excess . Drive strategy, financial performance, and growth for a regional Excess portfolio while building upon your existing strong broker and program manager relationships. Join a collaborative, fast-paced E&S/S team where your leadership can shape solutions others can’t offer and grow your career with us! #LI-AS1 #LI-remote Job Description Summary Are you...
Nationwide Chicago, IL Full Time
Nationwide
10/20/2026  
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
WTW
10/03/2026  
Healthcare Financial/Actuarial Senior Director
As a Health and Benefits Financial/Actuarial Senior Director, you will serve as the financial lead for large, complex client assignments. You’ll leverage your experience as a benefits financial/actuarial expert to make strategic recommendations on funding, plan design and innovative financial solutions. You will apply your financial management and data analytics expertise to solve complex client problems and to lead the development of new H&B intellectual capital.   The Role Communicates and delivers complex concepts and financial/actuarial/analytic results to effectively drive client action and improve plan performance Leads Medium to Large clients’ financial/actuarial engagements Develops and delivers the financial/actuarial strategy for a portfolio of Medium and/or Large clients Drives revenue growth through client sales of additional actuarial, financial, and/or risk solutions Provides consulting quality reviews and client delivery for all types of...
WTW Chicago, IL Full Time
Origami Risk
08/29/2026  
Regional Sales Manager
Overview The Regional Sales Manager is a front line manager who reports to our VP of Sales. You are someone who understands the science of selling and have successfully managed enterprise SaaS Sales representatives. You will be responsible for managing a team of high-performing sales professionals who are engaged in selling the Integrated Risk Management software products and services offered by Origami Risk and its subsidiaries. You will be responsible for ensuring that your team is always focused on the right activities to ensure a sustainable sales pipeline to achieve company sales goals. You are responsible for providing technical and metric driven support for your team to ensure continuity in the execution of a single sales process.   Starting base pay for this role is between $165,000 and $185,000. The actual base pay is dependent upon many factors, such as transferable skills, work experience, business needs, training, location, and market demands. The...
Origami Risk Chicago, IL Full Time
EPIC Insurance Brokers & Consultants
08/28/2026  
Commercial Insurance Broker / Account Executive - Law Firms
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 4,000 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 our...
EPIC Insurance Brokers & Consultants Chicago, IL
Guardian
10/15/2026  
Sales Analyst, Premier Market
Do you enjoy managing complex sales processes, collaborating across teams, and ensuring clients receive accurate and competitive benefit solutions? Guardian is seeking a Sales Analyst, Premier Markets to serve as a dedicated field resource supporting Sales Representatives and Client Management teams within our Group Benefits business. In this role, you will be responsible for managing RFPs, coordinating quote delivery, facilitating new business submissions, and partnering with internal stakeholders to help drive profitable growth. You will leverage strong analytical, organizational, and relationship-building skills to support sales success while delivering an exceptional customer experience. You Are A detail-oriented and process-driven professional who thrives in a fast-paced sales environment. You excel at managing multiple priorities,...
Guardian Chicago, IL Full Time
AmTrust Financial
10/09/2026  
Vice President, Underwriting
Overview The VP, Underwriting role is an experienced professional that should have a proven track record of leading functional leaders and teams and building profitable commercial lines books distributed via independent agencies, brokers, and wholesale partners, targeting small, middle-market and complex risks across various targeted industries. classes. The VP, Underwriting will be a “hands-on” technical expert focused on targeting a wide variety of commercial risks throughout the U.S. across. This individual maintains a solid understanding of AmTrust’s mission, vision, and values. Upholds the standards of the AmTrust organization. Reports to the Vice President – Midwest Region and has Underwriting responsibility across the 12 Midwest States: IL, IN, IA, KY, MI, MN, MO, ND, OH, SD, WI and WV Responsibilities · Leads leaders and a team that underwrites a profitable book of small, middle market and complex risks, employing the...
AmTrust Financial Chicago, IL Full Time
EPIC Insurance Brokers & Consultants
09/28/2026  
Senior 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 4,000 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 our...
EPIC Insurance Brokers & Consultants Chicago, IL
AIG
09/26/2026  
Senior Executive Underwriter, Excess Casualty
Join us as a Senior Executive  Underwriter, Excess Casualty to step up to a key team leadership role that will drive business growth. Make your 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 We are seeking a Senior Executive Underwriter to contribute to their industry leading Excess Casualty underwriting team.  AIG’s strong foundation as the market leader in this area has evolved through its long-term commitment to the marketplace, investment in technology, commitment...
AIG Chicago, IL Full Time
EPIC Insurance Brokers & Consultants
09/24/2026  
Personal Lines Account 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 our...
EPIC Insurance Brokers & Consultants Chicago, IL
The Hartford
09/22/2026  
Risk Engineering Technical Property Specialist-Midwest
Exec Consultant Risk Eng - KR07HE Sr Consultant Risk Engineering - KR08DE 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...
The Hartford Chicago, IL Full Time
CNA
09/12/2026  
VP, National Distribution Leader
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.  This position is responsible for achieving the distribution profitability goals for assigned national brokers across the US, ensuring optimal alignment between the various business units’ target appetites and the national broker’s book of business to maximize our profitable growth opportunities. Responsible for developing and executing initiatives to position CNA as a market leader and remain responsive and opportunistic in a rapidly changing distribution environment. Works in conjunction with home office and regional sales and production executives to drive CNA’s distribution strategy to advance CNA’s market share, visibility and brand. Acts as a primary relationship manager for multiple key...
CNA Chicago, IL Full Time
Amynta Group
09/11/2026  
National Sales Executive
We’re thrilled that you are interested in joining us here at the Amynta Group! The National Sales Executive– Specialty Equipment Insurance Services (Remote), is responsible for new sales, growth & development as well as implementation of the Extended Warranty product offerings for a defined region within North America. These responsibilities include establishing and meeting sales goals, enlisting new business prospects, promoting warranty program improvements, and shared responsibility for meeting business unit targets. Additionally, managing SG&A budget as assigned. Essential Responsibilities Engage the assigned dealership enterprises at all levels to assure sustainable market share growth for Insurance products and services. Meet or exceed sales targets, metrics, and goals. Support, promote, and facilitate the sales of Insurance products and services to a network of dealers and customers. Develop, maintain, and implement a territory-specific plan for the...
Amynta Group Chicago, IL Full Time
CNA
09/09/2026  
Underwriting Consultant (Technology P&C)
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 DESCRIPTION: For over three decades, CNA has been a trusted provider of insurance solutions for technology companies of all sizes—from emerging startups to global enterprises—across software, IT services, hardware, media, and telecommunications. Our Global Technology Practice delivers specialized coverages, including Technology Errors & Omissions (Tech E&O), Cyber Liability, and comprehensive international solutions, complemented by our traditional Property & Casualty capabilities. With deep industry expertise, flexible underwriting capabilities, and a collaborative approach, we design innovative insurance programs tailored to each client’s unique risk profile. CNA...
CNA Chicago, IL Full Time
Hiscox
09/05/2026  
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, Professional Risks Reporting to Regional Manager – A&E Location: Chicago, IL The Role: Hiscox USA is currently searching for a dynamic, engaging and solutions-oriented Underwriter to drive new professional liability business and complex renewal business within the A&E sector in the East Coast region. This position provides a unique opportunity for a professional liability generalist or an A&E/contractor 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 developers,...
Hiscox Chicago, IL Full Time
Hiscox
08/29/2026  
Underwriter, Professional Risks
Job Type: Permanent Build a brilliant future with Hiscox   Drive growth with an ambitious team of MPL Underwriters at Hiscox Position: Underwriter Reporting to: Regional Manager – MPL Location: Chicago, IL The Role: Hiscox USA is currently searching for a dynamic, engaging and solutions-oriented 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...
Hiscox Chicago, IL Full Time
Guardian
08/22/2026  
Sales Analyst, Premier Market
Do you enjoy managing complex sales processes, collaborating across teams, and ensuring clients receive accurate and competitive benefit solutions? Guardian is seeking a Sales Analyst, Premier Markets to serve as a dedicated field resource supporting Sales Representatives and Client Management teams within our Group Benefits business. In this role, you will be responsible for managing RFPs, coordinating quote delivery, facilitating new business submissions, and partnering with internal stakeholders to help drive profitable growth. You will leverage strong analytical, organizational, and relationship-building skills to support sales success while delivering an exceptional customer experience. You Are A detail-oriented and process-driven professional who thrives in a fast-paced sales environment. You excel at managing multiple priorities, collaborating across teams, and ensuring deliverables are completed accurately and on time. You balance customer needs with...
Guardian Chicago, IL Full Time
Ryan Specialty
08/22/2026  
VP of Sales - Employee Benefits
Position Summary The VP of Sales – Employee Benefits, is responsible for commanding territory performance and exceeding targets, through a culture of efficiency and innovation. The role collaborates across the enterprise to grow the benefits business. They shape industry discussions, ensure unwavering compliance with regulations, mitigate potential challenges and maximize profitability. What will your job entail? Position Summary: The VP of Sales – Employee Benefits, is responsible for commanding territory performance and exceeding targets, through a culture of efficiency and innovation. The role collaborates across the enterprise to grow the benefits business. They shape industry discussions, ensure unwavering compliance with regulations, mitigate potential challenges and maximize profitability. Location: Remote or Hybrid (based on location) Position Responsibilities: Develops and executes strategic vision and direction for the offices across...
Ryan Specialty Chicago, IL Full Time
Guardian
07/22/2026  
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

 

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