Senior Account Executive – Transportation (Trucking)

Position SummaryWe are seeking a Senior Account Executive with deep experience in commercial transportation underwriting, specifically trucking, to join our highly tenured, collaborative “Dream Team.” This role manages and expands an established multi-million dollar book of commercial trucking business, focusing on profitable growth, risk selection, and exceptional client service. You will apply strong underwriting judgment, use modern technologies, and partner closely with brokers, clients, and internal teams to drive results. You’ll also help shape the strategic direction of the transportation portfolio and support best‑practice development across underwriting teams.What will your job entail?Key Responsibilities:Underwriting & Portfolio ManagementDeliver profitable growth through effective risk selection, pricing, coverage recommendations, and remediation strategies within assigned authority.Manage and grow a commercial trucking book of business while ensuring underwriting quality and consistency.Conduct underwriting due diligence, gather required information, evaluate exposures, and prepare/interpret pricing models.Establish consistent underwriting best practices aligned with company guidelines, audit requirements, and compliance standards.Use AMS systems, internal underwriting platforms, rating models, and data analytics tools to support risk decisions.Business Development & Client RelationshipsBuild and maintain strong relationships with brokers, clients, and key transportation stakeholders.Identify and pursue new business opportunities in targeted trucking markets.Coordinate RFPs, create proposals, and negotiate terms, conditions, pricing, and coverage options.Identify and execute cross‑sell opportunities to deepen client relationships.Strategic LeadershipPartner with senior leadership to develop objectives, business strategies, and annual budget plans.Lead or support the development of innovative property and casualty products tailored to transportation customers.Monitor industry trends, competitor activity, and market needs to maintain a competitive edge in trucking.Technology & Process ImprovementEvaluate and implement emerging technologies—including AI and automation—to improve underwriting processes and operational efficiency.Contribute to continuous improvement of workflows, tools, and best practices.Team Collaboration & DevelopmentCollaborate closely with a highly experienced team known for exceptional support and partnership.Train and develop junior team members on underwriting techniques, compliance, documentation, and systems.Required Qualifications10+ years of Property & Casualty underwriting experience within commercial auto/transportation risks.P&C license and/or Surplus Lines licenseProficiency in data entry, AMS systems, Excel, and learning multiple systems that may not integrate seamlessly.Strong underwriting, analytical, and customer service skills.Demonstrate patience, adaptability, and enthusiasm for working in the trucking sector.High level of accuracy, organization, and follow‑through.Ability to work independently in a remote environment.Preferred QualificationsCPCU, AU, or other relevant insurance designations.BenefitsFull benefits package available for full time employees including but not limited to: Base salary plus bonus, Healthcare Options, Life Insurance and other ancillary enrollments, 401K with company match, generous paid time off, parental leave, tuition reimbursement, among others.Ryan Specialty is an Equal Opportunity Employer. We are committed to building and sustaining a diverse workforce throughout the organization. Our vision is an inclusive and equitable workplace where all employees are valued for and evaluated on their performance and contributions. Differences in race, creed, color, religious beliefs, physical or mental capabilities, gender identity or expression, sexual orientation, and many other characteristics bring together varied perspectives and add value to the service we provide our clients, trading partners, and communities. This policy extends to all aspects of our employment practices, including but not limited to, recruiting, hiring, discipline, firing, promoting, transferring, compensation, benefits, training, leaves of absence, and other terms, conditions, and benefits of employment.How We Support Our TeammatesRyan Specialty seeks to offer our employees a comprehensive and best-in-class benefits package that helps them — and their family members — achieve their physical, financial, and emotional well-being goals. In addition to paid time off for company holidays, vacation, sick and personal days, Ryan offers paid parental leave, mental health services and more.The target salary range for this position is $106,590.00 - $120,000.00 annually.The wage range for this role considers many factors, such as training, transferable skills, work experience, licensure and certification, business needs, and market demands. The pay range is subject to change