Head of Wholesale Underwriting
shepherd
13 days ago
Full-time
On-site
New York City
$350,000 - $425,000 USD yearly
Leadership
Moneyboard classification: Published base at/above threshold
Reported USD annual base: $350,000–$425,000
Original source: Ashby
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
[https://app.ashbyhq.com/api/images/user-content/cfdfd0b4-accb-41e6-8804-1216b89e5f82/0348cf6f-15dd-401e-8c20-de06e7a553fc/full-team.jpg]
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.
[https://app.ashbyhq.com/api/images/user-content/cfdfd0b4-accb-41e6-8804-1216b89e5f82/1441bf79-1d14-43aa-be40-ef718b7fdac3/nyc-wide.jpg]
🏗️ 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 http://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
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.
💼 ABOUT THE ROLE
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 fra
Reported USD annual base: $350,000–$425,000
Original source: Ashby
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
[https://app.ashbyhq.com/api/images/user-content/cfdfd0b4-accb-41e6-8804-1216b89e5f82/0348cf6f-15dd-401e-8c20-de06e7a553fc/full-team.jpg]
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.
[https://app.ashbyhq.com/api/images/user-content/cfdfd0b4-accb-41e6-8804-1216b89e5f82/1441bf79-1d14-43aa-be40-ef718b7fdac3/nyc-wide.jpg]
🏗️ 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 http://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
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.
💼 ABOUT THE ROLE
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 fra