Wholesale Underwriting Leader, E&S Growth

Shepherd; Chicago (IL); On-site; USD 350,000 - 425,000; Full time

Benefits offered by this job

Premium Healthcare

Fertility Benefits

Unlimited PTO

Daily meals

Office locations SF/NYC/Dallas–Fort W°

Leadership coaching

401(k) Plan

Dog-friendly office

Job summary

Shepherd is redefining commercial insurance with software, data, and AI. The Head of Wholesale Underwriting will build a national wholesale brand across E&S properties and financial lines, reporting to the Chief Insurance Officer.

The role requires 12+ years in wholesale E&S and a proven leadership track record. Based in a major city (New York, San Francisco, Chicago, Atlanta, Boston, LA, or Dallas–Fort Worth), you will set strategy, hire leaders, secure capacity, and drive growth with brokers

Qualifications

• 12+ years in the wholesale and E&S commercial P&C market, with leadership roles at a carrier, MGA/MGU, or wholesale specialty underwriting organization.
• Proven track record of building or scaling wholesale business with P&L ownership.
• Deep relationships with national and regional wholesale brokerage teams.
• Strong command of E&S wholesale channel dynamics, including regulation and compliance.
• Experience leading underwriters and setting authority frameworks.
• Executive presence to present strategy and results to leadership and reinsurers.
• Willingness to travel about 25% to meet brokers, partners, and the team.
• A bachelor's degree or equivalent experience; construction accounting, finance, or law is a plus.

Responsibilities

• Launch Shepherd's new wholesale business and brand.
• Define wholesale strategy, target products and classes, E&S appetite, broker partners, and growth targets.
• Work with Underwriting leadership to establish wholesale-exclusive classes and design new E&S products.
• Hire product underwriting leaders and develop underwriting guidelines, authority frameworks, and rating and forms.
• Structure a focused distribution strategy with wholesale broker partners and onboarding.
• Coordinate with capacity and reinsurance partners to secure E&S paper behind the program.
• Partner with Product, Engineering, and Data to design a wholesale submission-to-bind workflow.
• Own premium, profit, loss-ratio, retention, and expense results for the wholesale business.
• Hire and grow a team of wholesale leaders and support staff.
• Collaborate with Corporate Underwriting to set authority letters and run audits.
• Coordinate with Claims, Actuarial, Customer Experience and Finance to ensure well-underwritten, serviced, and reported business.

Skills

Wholesale E&S underwriting

Leadership

Broker relationships

Strategic planning

Travel readiness

Bachelor's degree or equivalent

Education

Bachelor's degree or equivalent

Job description

Shepherd is redefining commercial insurance with software, data, and AI. The Head of Wholesale Underwriting will build a national wholesale brand across E&S properties and financial lines, reporting to the Chief Insurance Officer.

The role requires 12+ years in wholesale E&S and a proven leadership track record. Based in a major city (New York, San Francisco, Chicago, Atlanta, Boston, LA, or Dallas–Fort Worth), you will set strategy, hire leaders, secure capacity, and drive growth with brokers