Head of Wholesale Underwriting

Build the insurance behind the physical world.

The world is building data centers, energy projects, hospitals, schools, and critical infrastructure. Every one of those projects needs insurance to move forward. Yet the process of getting that insurance still depends on scattered documents, manual work, and weeks of back-and-forth.

Shepherd is rebuilding commercial insurance with software, data, AI, and deep underwriting expertise. We started in construction and energy, where understanding the specifics of a project matters and better decisions have consequences far beyond a screen.

We develop insurance products, decide which risks to insure and how to price them, and partner with established insurers to back the coverage. We own the platform our team uses to turn complex submissions into coverage for the builders and operators shaping the world around us.

Real problems. Real ownership.

Our engineers, designers, underwriters, and actuaries build together. The problems span turning messy documents into reliable data, making pricing more precise, and designing AI agents that can take on increasingly complex underwriting work.

The ambition is a platform where experts spend more time on judgment and relationships, supported by software that handles the work around them. Join us to build systems whose decisions help real projects get built.

630+ customers / $500B+ insured project value

Capital to build. Partners to grow with.

$67M total funding / $42M Series B in March 2026

Shepherd is backed by Intact Private Capital, Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator. In March 2026, we announced a $42M Series B led by Intact Private Capital, bringing our total funding to $67M.

Intact is also a capacity partner. Alongside its investment, Intact works with Shepherd to bring insurance products to market. That relationship connects our platform and underwriting expertise with the resources of a global insurer.

A bigger opportunity ahead

We are investing in new insurance products, our underwriting team, and the path toward autonomous underwriting. For the people joining Shepherd, that means the chance to shape both the technology and the business it makes possible.

Our backing brings together investors who build technology companies and partners who understand insurance. We are building a company that earns the confidence of both.

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.

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.

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, 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

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.

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

🥕 Fertility benefits and family building support

🏖️ Flexible 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