Head of Finance

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

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.

You are a finance leader who wants to build the financial engine of a fast-growing insurance company. You’ve owned the plan, the numbers, and the controls, and you understand how capital and capacity shape an insurance business. You want to do the best work of your career at a company where finance sits at the center of how we grow.

You’d be a great fit if you have:

• 10+ years in finance, spanning FP&A, accounting, and strategic finance, including 4+ years leading teams at a venture-backed or high-growth company.

• Insurance finance experience at an MGA/MGU, carrier, reinsurer, or insurtech. You know commission and fee revenue, premium and claims flows, fiduciary accounts, bordereaux, and carrier and reinsurance reporting.

• Familiarity with risk-bearing structures such as captives, sidecars, quota shares, and fronting arrangements, and the accounting, cash, collateral, and regulatory requirements that come with them.

• A track record of running annual planning, forecasting, and budget-versus-actuals reviews on integrated models across revenue, headcount, OpEx, and cash.

• Strong command of close, audit, tax, treasury, and internal controls, including managing outsourced accounting partners.

• Experience leading or partnering closely with revenue operations, business operations, and analytics teams.

• Executive presence with a board,…