Underwriting Training and Development Specialist (Speciality Lines)

Ledgebrook is an InsurTech MGA on a mission to bring Specialty insurance into the modern era. Burdened with legacy technology and processes, the industry has not kept pace with the speed of innovation seen in other sectors. Positioned at the cutting edge of the next generation of InsurTech, Ledgebrook offers the best of both worlds: innovative world-class technology deployed by a leadership team armed with over 100 years of insurance expertise.

Our long-term vision is to become a diversified full stack Specialty re/insurer competing with legacy carriers in product lines & markets across the globe. To get there, Ledgebrook builds its premium base by rolling out a new Specialty product every ~6 months until we prove enough traction to raise a balance sheet, become a full stack carrier and eventually compete in the reinsurance markets. Our initial product is a domestic primary and excess GL E&S policies sourced via wholesale brokers.

At Ledgebrook, everything we do is driven by our culture: Care, Strive, Thrive Together. To succeed in modernizing the industry, we must first succeed in changing the way we do business. Talent density is our north star; fewer, better people working together as one. To that end we’ve replaced all individual incentives with generous equity packages. We play as a team, we win as a team. Everyone benefits handsomely from Ledgebrook’s success. 

Ledgebrook is a fully-remote US based company backed by top venture and family office investors including Brand Foundry, American Family Ventures, Duquesne Family Office, and Stephens Group. We’re a fully remote team prioritizing impact, ownership, and collaboration.

Ledgebrook seeks a Training and Development Specialist to join the Underwriting Excellence team. This role sits within the LBU Team and is responsible for the implementation and coordination of internal training programs, specifically for our Professional Liability product. 

Help foster a culture of learning, quality, and accountability.

Key Responsibilities

• 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.
• Training Logistics & Scheduling
• 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.
• Training Delivery
• Facilitates training on insurance appetite and company-specific systems.
• Onboarding Support: Assist in onboarding new hires, providing necessary training, and ensuring compliance.
• Help foster a culture of learning, quality, and accountability.
• Maintaining, tracking, and updating employee training records
• Needs Assessment & Analysis
• 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.

As a future Ledgebrook Training and Development Specialist, your experience and qualifications should include:

• 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. 

• 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

• Base Salary Range $75,000-$100,000. This is a good-faith compensation range based on what Ledgebrook reasonably expects to pay for this position at the time of this posting. Actual compensation may vary based on a variety of relevant factors including experience, qualifications, geographic location and other relevant factors. 
• Employees in this position are eligible to participate in Ledgebrook’s equity incentive program.