Commercial Casualty Underwriting Leader (Director)

What we do

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, CX, 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

Our investors

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.

Commercial Casualty Underwriting Leader (Director)

Shepherd is launching a Retail Commercial Casualty vertical, as an expansion to its current Primary and Excess Casualty offerings.The Commercial Casualty Underwriting Leader will play a lead role in building and shaping new industry segments from the ground up. This is an opportunity to help define the underwriting strategy, go-to-market, and drive long-term profitable growth for a core pillar of Shepherd’s business. We're looking for someone with 10+ years of commercial property underwriting experience, a proven track record of leadership, deep relationships in the retail channel, 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 casualty 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:

• 10+ years of commercial casualty 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: originating new business, quoting, binding, and building a casualty book while managing to loss-ratio and combined-ratio targets.

• Strong technical command of risk selection, exposure and loss analysis, loss development and trends, pricing, and coverage across Commercial General Liability, Commercial Auto, Workers’ Compensation and Excess Casualty.

• Experience structuring both primary and excess casualty programs, including guaranteed-cost and loss-sensitive programs such as large deductibles and self-insured retentions.

• Sound judgment on contractual risk transfer, additional insured requirements, manuscript endorsements, and emerging exposures.

• Disciplined portfolio management, including limits, accumulation, and clash exposure.

• 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.

About the Role

Shepherd's underwriting approach is 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 clients' specific needs.

In this role, you will:

• Define the strategy for retail commercial casualty, including target classes, lines of business, limits, attachment points, geographies, appetite, and growth and loss-ratio targets.

• Support the development of 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 exposure and loss-trend views.

• Underwrite new and renewal primary and excess casualty 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 casualty voice with brokers, clients, and other stakeholders.

• Hire, coach, and grow a team of casualty 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.

This is a position based in our New York City, San Francisco, Chicago, Los Angeles, or Dallas–Fort Worth offices.

Compensation

The base salary range for this role is $250,000 – $350,000, plus an annual performance bonus and equity in Shepherd. Offers within the range depend on location, 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 casualty vertical meant to scale nationally, so the guidelines, team, and tools get designed for where the book 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 this vertical, you set the standard every casualty underwriter after you inherits.

• 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 appetite, the broker list, or the first submission. You build the plan, make the calls, 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 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