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.

Head of Finance

About you

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, investors, carriers, and reinsurers. Fundraising experience is a plus.

• A bias toward systems and automation, including building finance and payments infrastructure with engineering.

• A bachelor’s degree in finance, accounting, economics, or a related field. CPA, CFA, or MBA is a plus.

About the Role

As Head of Finance, you will own Shepherd’s financial planning, accounting, controls, and reporting, and lead the operations teams that run our go-to-market engine. You’ll manage our Finance Lead and the Revenue Operations, Business Operations, and Analytics teams, work closely with the CEO, and partner with our Reinsurance and Capital Strategy leader as we add risk-bearing capacity.

In this role, you will:

Finance and planning

• Own the annual operating plan, long-range model, and monthly forecast and budget-versus-actuals reviews across revenue, headcount, OpEx, and cash.

• Build product-level contribution margin views so each new launch is judged on its economics.

• Own reporting packages for the board, investors, carriers, and reinsurers, and support future fundraising.

Capital, accounting, and controls

• Partner with both our Chief Insurance Officer and Reinsurance and Capital Strategy leader on the finance side of new risk-bearing structures, including captives, sidecars, quota shares, and fronting arrangements: modeling, accounting treatment, capital and collateral needs, and reporting.

• Build the entity, treasury, and cash infrastructure those structures need, including premium trust and fiduciary accounts, collateral, intercompany flows, and regulatory filings.

• Build scalable carrier payment tracking and bordereaux reconciliation across our carrier partners.

• Oversee close, audit, tax, and spend controls, and manage our outsourced accounting partner.

Operations

• Lead Analytics, Revenue Operations, and Business Operations across submission attribution, broker tiering, quota setting and compensation, underwriter enablement, partnerships, and marketing infrastructure.

• Tie plan, pipeline, and performance data together in one operating cadence.

• Hire, coach, and grow the finance and operations teams.

This is a position based in our New York City or San Francisco offices

Compensation

The base salary range for this role is $275,000 – $400,000, plus an annual performance bonus and equity in Shepherd. Offers within the range depend on location and experience.

Shepherd runs on four values. Here's what each one means in this seat.

• Think big, build big. We exist to protect progress and the industries that rely on it. The work here is aimed at a system that runs on its own, and the roadmap gets sequenced backward from that rather than forward from what's easy.

• Win together. We rise as one. We support each other, raise the bar, and celebrate collective success. Come set a standard the rest of the team inherits.

• Cross the aisle. Collaboration wins. We listen deeply, work across boundaries, and prioritize shared success over individual lanes. The best product calls here come from engineers who've sat with underwriters and underwriters who understand where the model breaks, and much of this job is listening closely enough on both sides to make that happen.

• Go get it. We act with urgency, move with confidence, take smart risks, and push forward with intention. Nobody hands you the roadmap, the data, or the meeting invite. You pull the failing runs, book the time with the underwriters, and decide what matters.

🏥 Premium Healthcare
100% contribution to health, dental, and vision

🥕 Fertility benefits and family building support

🏖️ Flexible PTO
Flexibility to take the time off, recharge, and perform

🥗 Daily lunches, dinners, and snacks
We work together, and enjoy meals together too

🖥️ SF, NYC, Dallas-Fort Worth, Chicago and 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