Professional Liability Underwriting Lead

About this role

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, 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

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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.

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🏗️ PROFESSIONAL LIABILITY UNDERWRITING LEAD

Shepherd is launching a Professional Liability product to support its existing Construction and Energy verticals as well as future verticals.The Professional Liability Underwriting Lead will play a lead role in building and shaping the new product expansion, with an initial focus on Errors & Omissions (E&O) and Miscellaneous Professional Liability (MPL). This is an opportunity to help define the underwriting strategy, go-to-market, and drive long-term profitable growth for the core pillars of Shepherd’s business. We're looking for someone with 8+ years of professional liability underwriting 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 professional liability 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:

- 8+ years of professional liability underwriting, with deep expertise across architects and engineers E&O as well as exposure to other industries such as technology, financial services, real estate, manufacturing or healthcare.

- A proven record of profitable growth: originating new business, quoting, binding, and building a professional liability book while managing to loss-ratio and combined-ratio targets.

- Strong technical command of risk selection, underwriting models, exposure and loss analysis, loss development and trends, pricing, and coverage across E&O and MPL.

- Strong technical command of risk selection, application and financial review, pricing, and coverage, including claims-made forms, retroactive dates, prior acts, extended reporting periods, retentions, and primary and excess structures.

- Sound judgment on manuscript endorsements, contractual liability, and emerging exposures across professional services, including technology, regulatory, and litigation trends.

- Established 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 professional liability, including target classes, lines of business, limits, attachment points, geographies, appetite, and growth and loss-ratio targets.

- Support the development of underwriting guidelines,…