Head of Wholesale Underwriting

Head Of Wholesale Underwriting

Shepherd is expanding its distribution and is launching a dedicated wholesale brand targeting E&S Property, Casualty and Financial Lines. The Head of Wholesale Underwriting will report to the Chief Insurance Officer and lead the development and execution of a newly-established, wholesale-exclusive insurance brand across multiple products and verticals. You will set the wholesale distribution strategy, define the products and appetite, hire the product line leaders and help secure the Excess & Surplus (E&S) capacity behind the program. This is a unique opportunity to help define the underwriting, brand and distribution strategies for a newly-established business unit. We're looking for someone with 12+ years of wholesale E&S experience, a proven track record of leadership, deep broker relationships, and an entrepreneurial mindset who is excited to build something new with modern technology and a forward-thinking team.

You are a builder who wants to shape the future of commercial insurance and do the best work of your career. You have deep wholesale expertise, a loyal broker network, and the drive to turn a blank page into a profitable book.

You'd be a great fit if you have:

• 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.
• A proven record of building or significantly scaling a wholesale business, product line, or channel, with P&L ownership for premium, profit, and loss-ratio results.
• Deep relationships with national and regional wholesale brokerage teams that can drive submission flow from day one.
• Strong command of how E&S business and the wholesale channel dynamics work, including surplus lines regulation and compliance, wholesale producer agreements, BOR protections, commission structures, and open brokerage and binding authority models.
• 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. A background in construction accounting, finance, or law is a plus.

This is a position based in New York City, San Francisco, Chicago, Atlanta, Boston, Los Angeles, or DallasFort Worth.

The base salary range for this role is $350,000 $425,000, plus an annual performance bonus and equity in Shepherd. Offers within the range depend on experience and the relationships and market following you bring.

Shepherd runs on four values. Here's what each one means in this seat.

• Think big, build big. We exist to protect progress and the industries that rely on it. You're building a wholesale business meant to scale nationally, so the products, partnerships, team, and tools get designed for where the channel is going, not just where it starts.
• Win together. We rise as one. We support each other, raise the bar, and celebrate collective success. As the first leader of our wholesale arm, you set the standard for every wholesale underwriter and broker partner who follows, and you build it hand in hand with our retail team.
• Cross the aisle. Collaboration wins. We listen deeply, work across boundaries, and prioritize shared success over individual lanes. The best underwriting tools here come from underwriters who sit with engineers and data scientists, and much of this job is making that partnership work.
• Go get it. We act with urgency, move with confidence, take smart risks, and push forward with intention. Nobody hands you the broker list, the appetite, or the first submission. You build the plan, open the doors, and bind the first deal.

Premium Healthcare 100% contribution to top-tier health, dental, and vision

Fertility Benefits & Family Building Support

Unlimited PTO Flexibility to take the time off, recharge, and perform

Daily Lunches, Dinners & Snacks We work together, and enjoy meals together too

SF, NYC, DallasFort Worth, Chicago & LA Offices

Professional Development Access to premium coaching, including leadership development

Competitive 401(k) Plan

Dog-Friendly Office Plenty of dogs to play with and make friends with in the SF office