Head of Wholesale Underwriting

Shepherd; Chicago (IL); On-site; USD 350,000 - 425,000; Full time

Benefits offered by this job

Premium Healthcare

Fertility Benefits

Unlimited PTO

Daily meals

Office locations SF/NYC/Dallas–Fort W°

Leadership coaching

401(k) Plan

Dog-friendly office

Job summary

Shepherd is redefining commercial insurance with software, data, and AI. The Head of Wholesale Underwriting will build a national wholesale brand across E&S properties and financial lines, reporting to the Chief Insurance Officer.

The role requires 12+ years in wholesale E&S and a proven leadership track record. Based in a major city (New York, San Francisco, Chicago, Atlanta, Boston, LA, or Dallas–Fort Worth), you will set strategy, hire leaders, secure capacity, and drive growth with brokers

Qualifications

• 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.
• Proven track record of building or scaling wholesale business with P&L ownership.
• Deep relationships with national and regional wholesale brokerage teams.
• Strong command of E&S wholesale channel dynamics, including regulation and compliance.
• Experience leading underwriters and setting authority frameworks.
• Executive presence to present strategy and results to leadership and reinsurers.
• Willingness to travel about 25% to meet brokers, partners, and the team.
• A bachelor's degree or equivalent experience; construction accounting, finance, or law is a plus.

Responsibilities

• Launch Shepherd's new wholesale business and brand.
• Define wholesale strategy, target products and classes, E&S appetite, broker partners, and growth targets.
• Work with Underwriting leadership to establish wholesale-exclusive classes and design new E&S products.
• Hire product underwriting leaders and develop underwriting guidelines, authority frameworks, and rating and forms.
• Structure a focused distribution strategy with wholesale broker partners and onboarding.
• Coordinate with capacity and reinsurance partners to secure E&S paper behind the program.
• Partner with Product, Engineering, and Data to design a wholesale submission-to-bind workflow.
• Own premium, profit, loss-ratio, retention, and expense results for the wholesale business.
• Hire and grow a team of wholesale leaders and support staff.
• Collaborate with Corporate Underwriting to set authority letters and run audits.
• Coordinate with Claims, Actuarial, Customer Experience and Finance to ensure well-underwritten, serviced, and reported business.

Skills

Wholesale E&S underwriting

Leadership

Broker relationships

Strategic planning

Travel readiness

Bachelor's degree or equivalent

Education

Bachelor's degree or equivalent

Job description

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.

$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.

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

• 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.

Responsibilities

• 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

• 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 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
• Official Offices: SF, NYC, Dallas–Fort Worth, Chicago, and LA
• 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