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 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. Youve 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.

Youd 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 bachelors degree in finance accounting economics or a related field. CPA CFA or MBA is a plus.

As Head of Finance you will own Shepherds financial planning accounting controls and reporting and lead the operations teams that run our go-to-market engine. Youll 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

The base salary range for this role is $275000 $400000 plus an annual performance bonus and equity in Shepherd. Offers within the range depend on location and experience.

Shepherd runs on four values. Heres 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 whats 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 whove 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

Required Experience:

Director