Executive Lead Underwriter

Coleman Search Group, Inc.; United States; Remote; USD 100,000 - 150,000; Full time

Job summary

A leading recruitment agency is seeking an Executive Lead Underwriter to head underwriting for large commercial trucking accounts worth over $1.5M. This remote role requires a candidate with over 8 years of experience in commercial trucking underwriting and strong expertise in Captives and Retro markets. Responsibilities include driving underwriting strategy and cultivating agency relationships to support business growth. This position offers significant career development opportunities in a collaborative environment.

Qualifications

• 8+ years of commercial trucking underwriting experience, with 5+ years supporting large accounts of +$1M.
• Strong expertise around Captives, SIR’s, and Retros.
• Proven track record of managing production and profitability at a regional or national level.

Responsibilities

• Underwrite large commercial accounts and grow a new book of business.
• Drive underwriting strategy, including pricing, excess structures, and product development.
• Cultivate agency relationships through site visits, audits, and strategic communication.

Skills

Commercial trucking underwriting experience

Captives expertise

Strong producer relationship-building

Risk evaluation

Job description

Coleman Search Group is working with a legacy commercial carrier to identify an Executive Lead Underwriter to lead underwriting efforts as they build-out an Alternative Markets division dedicated to Large Accounts within the trucking industry. Backed by the financial stability of a multi-billion dollar parent company, our client has demonstrated stability, growth, and success within the trucking and transportation industry for over 80 years and is now primed for expansion!

This is a remote production role dedicated to new business. As such, this individual should possess an entrepreneurial mindset along with deep technical expertise and agency relationships within the Captive, SIR, and Retro space. This is an opportunity to mold, shape, and develop a new business unit. The ideal candidate will be someone that embraces fluidity, autonomy, and field authority, and can be successful within a company culture of collaboration, innovation, and teamwork. Travel of approximately 30% should be expected. This position comes with significant career growth opportunity!

About the Role

The Executive Lead Underwriter will lead underwriting efforts for large commercial trucking accounts with premiums of $1.5 – 2.5+M and more than 150 power units. This role combines technical underwriting expertise, strategic account management, and strong producer relationship-building. The position may also include supervisory responsibilities for underwriting professionals and will play a key role in shaping underwriting processes, guidelines, and product strategy.

• Underwrite large commercial accounts and grow a new book of business
• Utilize expertise in SIRs, large deductibles, captives, and retrospective rating plans.
• Drive underwriting strategy, including pricing, excess structures, and product development.
• Evaluate risk data, including loss control reports, MVRs, and financial statements.
• Ensure accurate risk classification, policy forms, and pricing for new and renewal business.
• Cultivate agency relationships through site visits, audits, and strategic communication.
• Deliver presentations on coverage and services to key stakeholders.
• Provide technical mentorship to Assistant Underwriters on endorsements and policy actions.
• Contribute to the development of new products and process enhancements.
• Ability to attract, mentor, and develop staff as the business unit grows.

Qualifications

• 8+ years of commercial trucking underwriting experience, with 5+ years supporting large accounts of +$1M.
• Strong expertise around Captives, SIR’s, and Retros.
• Deep knowledge of casualty insurance markets, industry trends, and regulations.
• Proven track record of managing production and profitability at a regional or national level.

Coleman Search Group has been dedicated to the insurance industry since 2009, offering more than 40 years of inhouse industry knowledge and expertise. Since inception we’ve had the privilege of representing and strategically partnering with more than 40 insurance carriers, firms, and organizations on hundreds of hires.