Underwriting Training and Development Specialist

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 is responsible for the development, maintenance, and implementation of internal training programs, specifically for our General Casualty product. 

This position is instrumental in promoting a culture built on continuous learning, high quality, and mutual accountability.

Key Responsibilities

Curriculum Development for Ledgebrook University

• Collaborate within the Underwriting Excellence team to determine training, technology, and process improvement needs.
• Assist with the creation of comprehensive training materials (presentations, manuals, video conferencing, and in-person sessions) for new and current underwriting staff.
• Ensure adherence to internal underwriting guidelines and external regulatory requirements.
• Update training materials regularly to reflect changes in appetite and internal software/systems.

Training Delivery

• Facilitates training on insurance appetite and company-specific systems.
• Assist in providing feedback on, and refining the training process
• Help foster a culture of learning, quality, and accountability.
• Onboarding Support: Assist in onboarding new hires, providing necessary training, and ensuring compliance with safety or industry regulations.

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 in a training or instructional role or general/technical underwriting experience in (3-5 years).
• 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 subject matter experts. 
• Must have a strong stance on olives.

Important - only for candidates applying from the U.S.:

Please note: This position is open only to candidates who are authorized to work in the United States without the need for current or future employer-sponsored work authorization. We are unable to offer visa sponsorship at this time.

• Competitive salary and meaningful equity ownership
• Health Insurance - 100% employer-paid option available
• Additional benefits available include 401k plan, dental, vision & other options
• Remote work, flexible hours
• Unlimited time off policy
• Ownership, autonomy, purpose