Commercial Property Underwriting Leader (Director)

Shepherd; Chicago (IL); Vor Ort; USD 250.000 - 350.000; Vollzeit

Benefits dieser Stelle

Premium Healthcare

Fertility Benefits

Unlimited PTO

Daily lunches

SF, NYC, Dallas–Fort Worth, Chicago &

Professional Development

401(k) Plan

Dog Friendly Office

Zusammenfassung

Shepherd is seeking a Commercial Property Underwriting Leader to build and shape a new retail property vertical nationwide. This role leads strategy, risk; partners with Product, Engineering and Data to scale an AI-enabled underwriting platform.

Based in one of our US offices, you will define the production approach, oversee a team of underwriters, and drive profitable growth while maintaining strong broker relationships and executive presence.

Qualifikationen

• 10+ years of commercial property underwriting with retail middle market and large accounts.
• Proven profitable growth: quoting, binding, and building a property book while managing loss-ratio targets.
• Strong command of risk selection, COPE analysis, valuation, pricing, coverage, and manuscript forms.
• Hands-on CAT modeling experience (RMS / AIR / Verisk) and disciplined exposure management.
• Established retail broker relationships at regional and national levels.
• People leadership experience leading or managing underwriters, including setting authority and audits.
• Executive presence to present strategy and results to leadership and partners.
• Willingness to travel about 25% to meet brokers and partners.
• Bachelor's degree or equivalent experience.

Aufgaben

• Define the production strategy for retail commercial property, including target classes, TIV bands, geographies, appetite, and growth and loss-ratio targets.
• Support in writing the 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 CAT-exposure views.
• Underwrite new and renewal primary and excess property 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 property voice with brokers, clients, and other stakeholders.
• Hire, coach, and grow a team of property underwriters and support staff as the book scales.
• Work with Claims, Actuarial, Customer Experience and Finance so the business is underwritten, serviced, and reported well.

Kenntnisse

Commercial property underwriting

Leadership

Retail broker relationships

CAT modeling

Underwriting guidelines

Team leadership

Real estate experience

Ausbildung

Bachelor's degree or equivalent

Tools

RMS

AIR

Verisk

Jobbeschreibung

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

Our investors B 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 Property Underwriting Leader (Director)

Shepherd is launching a Retail Commercial Property vertical as an expansion to its current Property and Inland Marine offerings. The Commercial Property 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 property 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 property 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: quoting, binding, and building a property book while managing to loss‑ratio and combined‑ratio targets.
• Strong technical command of risk selection, COPE analysis, valuation, pricing, coverage, primary and excess layering, and manuscript forms.
• Hands‑on CAT modeling experience (RMS / AIR / Verisk) and disciplined aggregate and exposure management.
• 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 using our AI‑native platform. 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 production strategy for retail commercial property, including target classes, TIV bands, geographies, appetite, and growth and loss‑ratio targets.
• Support in writing the 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 CAT‑exposure views.
• Underwrite new and renewal primary and excess property 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 property voice with brokers, clients, and other stakeholders.
• Hire, coach, and grow a team of property 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.

Compensation Range: $250K - $350K

How We Work

• Think big, build big. We exist to protect progress and the industries that rely on it. We'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 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

Benefits

• Premium Healthcare 100% contribution to health, dental, and vision
• Fertility Benefits & Family Building Support
• Flexible PTO
• 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