Head of Retail Property Underwriting

Shepherd; San Francisco (CA); On-site; USD 250,000 - 350,000; Full time

Benefits offered by this job

Premium Healthcare

Fertility Benefits

Unlimited PTO

Daily Meals

Office network (SF/NYC/Dallas/Chicago/

Professional Development

Competitive 401(k) Plan

Dog-friendly office

Job summary

Shepherd is seeking a Commercial Property Underwriting Leader to spearhead a new Retail Commercial Property vertical, shaping underwriting strategy, go-to-market plans, and long‑term profitable growth. The role requires a decade of property underwriting expertise, strong leadership, and a robust broker network to drive early submissions and scale the book with modern technology.

You will lead strategy, guidelines, pricing tools, and CAT exposure views, while partnering with Product, Engineering,

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.
• A proven record of profitable growth: quoting, binding, and building a property book while managing to 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 broker relationships

Leadership experience

CAT modeling

Executive presence

Education

Bachelor's degree or equivalent experience

Tools

RMS

AIR

Verisk

Job description

Shepherd is seeking a Commercial Property Underwriting Leader to spearhead a new Retail Commercial Property vertical, shaping underwriting strategy, go-to-market plans, and long‑term profitable growth. The role requires a decade of property underwriting expertise, strong leadership, and a robust broker network to drive early submissions and scale the book with modern technology.

You will lead strategy, guidelines, pricing tools, and CAT exposure views, while partnering with Product, Engineering,