Underwriting Training and Development Specialist – Specialty Lines

Ledgebrook

Training and Development Specialist for Underwriting at Ledgebrook InsurTech MGA. Responsible for creating and delivering training materials and programs for underwriting staff.

Posted 6/30/2026full-timeRemote • 🇺🇸 United StatesMid-LevelSeniorWebsite

About the role

Key responsibilities & impact

Curriculum Development for Ledgebrook University Create comprehensive training materials (presentations, manuals, video conferencing, and in-person sessions) for new and current underwriting staff to improve underwriting skills, system proficiency and compliance knowledge.
Expand and grow content for e-learning, virtual instructor-led training, and in-person workshops.
Update training materials regularly to reflect changes in appetite and internal software/systems.
Collaborate within the Underwriting Excellence team to determine training, technology, and process improvement needs.
Ensure adherence to internal underwriting guidelines and external regulatory requirements.
Coordinate and schedule virtual onboarding and training sessions for new hire UWs with LBU Officer, subject matter experts and other identified stakeholders.
Manages all aspects of in-person workshops (Road Shows), including but not limited to site selection, budget oversight, and execution of on-site logistics.
Promotion of upcoming training opportunities and workshops to employees to ensure high participation.
Facilitates training on insurance appetite and company-specific systems.
Assist in onboarding new hires, providing necessary training, and ensuring compliance.
Maintaining, tracking, and updating employee training records.
Collaborate within the UW Excellence Team to identify skill gaps, performance issues, and training needs within the Underwriting team.
Regularly seeking and acting on feedback from trainees and stakeholders.

Requirements

What you’ll need

Previous experience as a Professional Liability Underwriter (3-5 years) or a Professional Liability Subject Matter Expert - Allied Healthcare, Miscellaneous PL (Real Estate, Insurance Agents/Brokers, Consultants), or Cyber Liability.
Ability to design and produce instructional materials, including educational modules, onboarding resources, and standard operating procedures (SOPs).
Strong project management and scheduling skills to handle multiple training initiatives.
Excellent verbal and written communication skills for instructing and presenting.
Skilled in diverse learning technologies, including LMS, e-learning platforms, and video conferencing tools.
Demonstrates flexibility in response to evolving technology, underwriting appetite, and organizational objectives.
Strong interpersonal skills to engage trainees and work with other subject matter experts.

Benefits

Comp & perks

Full remote flexibility and asynchronous work culture
Unlimited PTO and fully paid sick leave
Comprehensive health benefits, including medical, dental, and vision coverage, plus HSA and FSA options
Additional financial protection and retirement benefits, including a 401(k), company-paid life insurance, and disability coverage
A high degree of ownership, autonomy, and the opportunity to help build and shape a growing company
The chance to make a meaningful impact while working alongside an ambitious, high-performing team
Exposure to the challenges and opportunities of a fast-growing startup environment

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

Curriculum DevelopmentInstructional DesignProject ManagementTraining Material CreationCompliance KnowledgeOnboarding ResourcesStandard Operating Procedures (SOPs)Training Needs AssessmentPerformance ImprovementContent Expansion

Soft Skills

Excellent Communication SkillsInterpersonal SkillsFlexibilityCollaborationFeedback Responsiveness