80 transportation jobs found in Chicago

Job Description Sompo has a unique opportunity for a 2026 Sompo Underwriting Trainee in our Chicago, IL office. Our Trainee Program is an 18-month program beginning in July 2026 designed to equip you with the essential business and technical skills needed to build a successful career in insurance. As an Underwriting Trainee you will work alongside the most experienced underwriters in the industry to gain in-depth knowledge of our business units and underwriting philosophy through on-the-job learning, workplace mentoring. Our Trainees work directly on their products’ accounts, building relationships and identifying customers’ needs. This rigorous curriculum also includes training in negotiation, risk analysis and relationship management. Sompo’s Trainee Program serves as a launchpad for career advancement, empowering you to acquire the knowledge and skills essential for success in your respective field. What can I expect as a Underwriting Trainee? On-The-Job Learning...

Specialty Programs Group – Transportation (SPGT) is seeking the position of Assistant Vice-President of Business Development. This position is looking for a self-motivated individual with a strong knowledge of insurance, wholesale and retail distribution, and marketing.  Responsible for managing and executing each assigned specialty segment strategy for distribution excellence for your designated geography. At the same time continue to build each brand, leading to increased industry recognition, revenue, relevance, and respect amongst our target audience: agents, brokers, carriers, and employees. Support the operating, financial and strategic goals for all SPGT Divisions in collaboration with the respective leaders. Key Areas of Responsibility: Insurance Product Line Responsibility: Represent all SPGT Divisions, products and services to all sizes of 3rd party insurance distributors, in the assigned geography, to drive profitable growth.  New Relationships - Sales...

Specialty Programs Group – Transportation (SPGT) is seeking the position of Assistant Vice-President of Business Development. This position is looking for a self-motivated individual with a strong knowledge of insurance, wholesale and retail distribution, and marketing.  Responsible for managing and executing each assigned specialty segment strategy for distribution excellence for your designated geography. At the same time continue to build each brand, leading to increased industry recognition, revenue, relevance, and respect amongst our target audience: agents, brokers, carriers, and employees. Support the operating, financial and strategic goals for all SPGT Divisions in collaboration with the respective leaders. Key Areas of Responsibility: Insurance Product Line Responsibility: Represent all SPGT Divisions, products and services to all sizes of 3rd party insurance distributors, in the assigned geography, to drive profitable growth.  New Relationships - Sales...

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 looking for a Senior UX Designer to join our team. Our UX Design team within the Digital Solutions group shapes user experiences across RT Specialty’s ecosystem of digital products, including internal tools and client‑facing platforms. This position offers a hybrid schedule with three days in the office and two days working from home in our Chicago, IL or Buffalo, NY locations. We are looking for a Senior UX Designer, with “full-stack” skills (UI + UX/IA + UX research) skills – strong UI skills are a must....

Job Description Are you looking for your next opportunity?   Sompo has a unique opportunity for a Vice President and Midwest Regional Manager o n our Commercial Property Middle Market team.   Our Commercial Property Middle Market team offers property coverage to commercial accounts with a focus on mid to larger mid-size U.S. domiciled companies across a broad base of occupancy types, including but not limited to: Light & Heavy Manufacturing, Food Processing, Metal Working, Warehousing, Retail Stores, Wholesale Suppliers, Hospitals & Healthcare, Educational Institutions, Transportation. The Middle Market Commercial Specialty Property team offers both 100% single carrier capacity and quota share capacity.  We take a collaborative approach to loss control and work closely with our Risk Control Engineers to mitigate risk and partner with our clients to protect their business value. We seek to build long-term relationships with our retail brokers and...

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 RT Connector, a division of Ryan Specialty, is seeking a Product Manager to join our team in Chicago, IL. We are a dynamic, fast-growing organization that offers an exciting opportunity for professionals looking to advance their careers in a high-energy, collaborative environment. The Product Manager will own the execution and evolution of RT Connector’s retail agent platform, ensuring it delivers a seamless, intuitive experience enabling retail agents to efficiently do business with RT Specialty. This role plays a critical part...

MSIG USA continues to grow!  Company Overview: MSIG USA is the US-based subsidiary of  MS&AD Insurance Group Holdings, Inc. , one of the world’s top P&C carriers and a global Class 15 insurer, with A+ ratings and a reach that spans 40+ countries and regions. Leveraging our 350-year heritage, MSIG USA brings the financial strength, expertise, and global footprint to offer commercial insurance solutions that address your business’s unique risks. Summary: Produce, underwrite and service profitable Marine business in accordance with all department guidelines.  Assumes a leadership role in the organization to positively influence staff and promote a positive image of MSIG in the marketplace. Develop agency relationships and build a profitable book of business. Essential Functions: Produces, selects and underwrites Marine risks within delegated underwriting authority, including construction, transportation or other classes of Inland Marine as...

MSIG USA continues to grow!  Company Overview: MSIG USA is the US-based subsidiary of  MS&AD Insurance Group Holdings, Inc. , one of the world’s top P&C carriers and a global Class 15 insurer, with A+ ratings and a reach that spans 40+ countries and regions. Leveraging our 350-year heritage, MSIG USA brings the financial strength, expertise, and global footprint to offer commercial insurance solutions that address your business’s unique risks. Summary: Produce, underwrite and service profitable Inland Marine business in accordance with all department guidelines.  Assumes a leadership role in the organization to positively influence staff and promote a positive image of MSIG in the marketplace. Develop agency relationships and build a profitable book of business. Essential Functions: Produces, selects and underwrites Inland Marine risks within delegated underwriting authority, including construction, transportation or other classes of Inland Marine...

Who Are We? Taking care of our customers, our communities and each other. That’s the Travelers Promise. By honoring this commitment, we have maintained our reputation as one of the best property casualty insurers in the industry for over 170 years. Join us to discover a culture that is rooted in innovation and thrives on collaboration. Imagine loving what you do and where you do it. Job Category Underwriting Compensation Overview The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program,...

Company Argo Group Argo Group is an underwriter of specialty insurance products in the property and casualty market. Argo offers a full line of products and services designed to meet the unique coverage and claims-handling needs of businesses. The Argo entities are wholly-owned subsidiaries of Clearbrook Group Holdings Inc. Job Description Senior Underwriter, Inland Marine, Argo Group At Argo Group, we invite you to elevate your career as a Senior Underwriter, Inland Marine, joining a vibrant team with a bold vision for growth and innovation based out of one of our offices, Chicago (IL), Omaha (NE), Springfield (MO), Albany (NY), or New York City (NY). Make Your Mark at Argo Group Are you ready to be a catalyst for change? Our underwriting teams are trailblazers, delivering cutting-edge insurance solutions in Inland Marine, Casualty, Construction, Environmental, and Specialty Lines. We’re not simply adapting to a changing world; we’re leading the...

MSIG USA continues to grow!  Company Overview: MSIG USA is the US-based subsidiary of  MS&AD Insurance Group Holdings, Inc. , one of the world’s top P&C carriers and a global Class 15 insurer, with A+ ratings and a reach that spans 40+ countries and regions. Leveraging our 350-year heritage, MSIG USA brings the financial strength, expertise, and global footprint to offer commercial insurance solutions that address your business’s unique risks. This underwriter role is focused on the construction business.  Responsible for underwriting, and servicing profitable builders risk business through relationships with construction brokers.  Essential Functions: Underwrites, and services both project and master builders risks within delegated underwriting authority.  Will also underwrite related Inland Marine classes, including contractors equipment, riggers liability, installation projects, and transportation.  Profitability & Underwriting Quality:...

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:  Independence Pet Holdings (IPH) is undertaking a multi-year enterprise transformation to modernize its insurance technology ecosystem and build a scalable, digital-first operating model across its MGAs.  The Sr. Technology Program Manager, Global Transformation will lead the...

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:  Independence Pet Holdings (IPH) is undertaking a multi-year enterprise transformation to modernize its insurance technology ecosystem and build a scalable, digital-first operating model across its MGAs.  The Sr. Technology Program Manager, Global Transformation will lead the...

Complex Claims Director – Management Liability At AIG, we are reimagining the way we help customers to manage risk. Join us as a Complex Claims Director – Management Liability 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 Claims Our Claims teams are the proven problem solvers of choice for clients, delivering consistent technical excellence and showcasing our service differentiation to create an unparalleled global claims handling experience. Through a robust stakeholder feedback loop and supported by consistent processes and leadership, we take pride in delivering responsive, fair and professional service with empathy and efficiency. How you will create an impact An employee in this role will be responsible for handling all aspects of complex directors & officers claims, including securities class actions, with opportunity to handle high exposure employment...

Job Description 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 About the Job We are seeking...

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...

At AIG, we are reimagining the way we help customers to manage risk. Join us as a Complex Claims Director 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 Excess Casualty Claims Our Claims teams are the proven problem solvers of choice for clients, delivering consistent technical excellence and showcasing our service differentiation to create an unparalleled global claims handling experience. Through a robust stakeholder feedback loop and supported by consistent processes and leadership, we take pride in delivering responsive, fair and professional service with empathy and efficiency. How you will create an impact Are you interested in handling some of the largest and most complex Casualty claims in the industry? Your deep technical claims expertise will be put to the test in the investigation, evaluation and disposition of new and existing 3rd party property and casualty...

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...

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...

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...