Head of Wholesale Underwriting

What We Do

Commercial insurance still runs on processes built decades ago. Underwriting is slow, and pricing leans on broad averages instead of the specifics of each risk. Technology can change how commercial risk is priced and managed, as long as it's paired with real underwriting expertise. The companies that get this right will shape the next era of the industry, and Shepherd intends to lead it.

Shepherd is a Managing General Underwriter (MGU) building the fastest and smartest AI-native commercial risk platform in the industry, where underwriters, data, and automation work together. The result is faster decisions for our broker partners and pricing that reflects the actual risk.

We started where the gap is widest: construction and energy, two of the most complex and highest-hazard segments in commercial insurance. Today we write Primary and Excess Casualty, Builder’s Risk, and Workers' Compensation distributed through a nationwide network of retail brokers. Our mission is to make risk frictionless for the builders and operators shaping the physical world, from concept through construction and into decades of operation.

🚀 Our Investors

Shepherd has raised over $67M, including a $42M Series B led by Intact Private Capital. Intact also partners with Shepherd to provide capacity across its insurance products. Shepherd is also backed by leading institutional investors, including Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator.

🏗️ 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.

🎯 About You

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.

💼 About the Role

Shepherd's underwriting approach is broker and client-centric with a heavy emphasis on an efficient process. Our goal is to leverage our technology and data to make quick, informed underwriting decisions tailored to our brokers' specific needs.

In this role, you will:

• Launch Shepherd's new wholesale business and brand.

• Define the wholesale strategy, including target products and classes, E&S appetite, broker partners, and growth and loss-ratio targets by line of business.

• Work with Underwriting leadership to establish wholesale-exclusive classes and design new E&S products where the opportunity is greatest.

• Hire product underwriting leaders and support the development of the underwriting guidelines, authority frameworks, referral rules, rating approach, and forms for the respective wholesale / E&S lines of business.

• Structure a focused distribution strategy with our wholesale broker partners by product line, helping to onboard wholesale broker partners, setting producer and market partner agreements, and building Shepherd's reputation as a go-to market for wholesale brokers.

• Work with capacity and reinsurance partners to secure and structure the E&S paper behind the program, and keep those partners informed on results.

• Partner with Product, Engineering, and Data to design a wholesale submission-to-bind workflow to create a frictionless experience for our wholesale partners for each product.

• Own premium, profit, loss-ratio, retention, and expense results for the wholesale business.

• Hire, coach, and grow a team of wholesale product line leaders, underwriters, distribution leaders, and support staff as the business 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.

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

💰 Compensation

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.

⚡ How We Work

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.

🌟 Benefits

🏥 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, Dallas - Fort 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

#LI-Onsite

How we work

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. The work here is aimed at a system that runs on its own, and the roadmap gets sequenced backward from that rather than forward from what's easy.

• Win together. We rise as one. We support each other, raise the bar, and celebrate collective success. Come set a standard the rest of the team inherits.

• Cross the aisle. Collaboration wins. We listen deeply, work across boundaries, and prioritize shared success over individual lanes. The best product calls here come from engineers who've sat with underwriters and underwriters who understand where the model breaks, and much of this job is listening closely enough on both sides to make that happen.

• Go get it. We act with urgency, move with confidence, take smart risks, and push forward with intention. Nobody hands you the roadmap, the data, or the meeting invite. You pull the failing runs, book the time with the underwriters, and decide what matters.

Benefits

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

🥕 Fertility benefits and family building support

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

🥗 Daily lunches, dinners, and snacks
We work together, and enjoy meals together too

🖥️ SF, NYC, Dallas-Fort Worth, Chicago and 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