AI-Driven Retail Property Underwriting Director

Shepherd; Los Angeles (CA); On-site; USD 250,000 - 350,000; Full time

Benefits offered by this job

Premium Healthcare

Family building support

Unlimited PTO

Daily meals

Office in SF, NYC, Dallas–Fort Worth,

Professional development

401(k) plan

Dog-friendly office

Job summary

Shepherd is building a new Commercial Property vertical and seeks a leader to define the production strategy for retail property, set underwriting guidelines, and drive growth across the book with a modern AI‑native platform.

You will lead underwriting, mentor a team, and collaborate with Product, Engineering, and Data to design workflows and pricing tools. A bachelor’s degree is required and travel ~25% is expected.

Qualifications

• 10+ years of commercial property underwriting, with deep expertise in retail middle market and large accounts across classes such as real estate, retail, hospitality, manufacturing, and technology.
• Proven record of profitable growth: quoting, binding, and building a property book while managing loss‑ratio and combined‑ratio targets.
• Strong technical command of risk selection, COPE analysis, valuation, pricing, coverage, primary and excess layering, and manuscript forms.
• Hands‑on CAT modeling experience (RMS / AIR / Verisk) and disciplined aggregate and exposure management.
• Established retail broker relationships at the regional and national level that can drive submission flow from day one.
• People leadership experience leading, mentoring, or managing underwriters, including setting authority and running underwriting audits.
• Executive presence to present strategy and results to leadership, capacity partners, and reinsurers.
• Comfort with ambiguity: you make sound decisions with incomplete information and adapt quickly as the business evolves.
• Willingness to travel about 25% to meet brokers, partners, and the team.
• A bachelor’s degree or equivalent experience.

Responsibilities

• Define the production strategy for retail commercial property, including target classes, TIV bands, geographies, appetite, and growth and loss‑ratio targets.
• Support in writing the underwriting guidelines, authority framework, referral rules, and rating approach.
• Partner with Product, Engineering, and Data to design the submission‑to‑bind workflow, pricing tools, and CAT‑exposure views.
• Underwrite new and renewal primary and excess property within your authority.
• Own premium, profit, loss‑ratio, retention, and expense results for the vertical.
• Use your retail broker relationships to drive submission flow in the first year, and serve as Shepherd’s senior property voice with brokers, clients, and other stakeholders.
• Hire, coach, and grow a team of property underwriters and support staff as the book scales.
• Work with Corporate Underwriting to help set letters of authority, run underwriting audits, and coach from the results.
• Work with Claims, Actuarial, Customer Experience and Finance so the business is underwritten, serviced, and reported well.

Skills

Commercial property underwriting

Retail middle market & large accounts

Broker relationships

Leadership / mentoring underwriters

CAT modeling (RMS / AIR / Verisk)

Guidelines & authority framework

Executive presence

Travel ~25%

Bachelor’s degree or equivalent

Education

Bachelor’s degree or equivalent experience in relevant field

Tools

RMS

AIR

Verisk

Job description

Shepherd is building a new Commercial Property vertical and seeks a leader to define the production strategy for retail property, set underwriting guidelines, and drive growth across the book with a modern AI‑native platform.

You will lead underwriting, mentor a team, and collaborate with Product, Engineering, and Data to design workflows and pricing tools. A bachelor’s degree is required and travel ~25% is expected.