Head of FinanceAbout youYou 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 RoleAs 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
CompensationThe 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.
How We WorkShepherd 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. You're building the finance function for a company planning to reach $1B+ in premium, so the models, controls, and entity structures get designed for that scale from the start.
- Win together. We rise as one. We support each other, raise the bar, and celebrate collective success. As our first Head of Finance, you set the standard for how every team plans, spends, and measures results.
- Cross the aisle. Collaboration wins. We listen deeply, work across boundaries, and prioritize shared success over individual lanes. Underwriting, reinsurance and capital, engineering, and leadership all rely on finance to make decisions, and much of this job is making those partnerships work.
- Go get it. We act with urgency, move with confidence, take smart risks, and push forward with intention. The plan, the controls, and the structures behind our next stage of growth are still to be built. You build them and make the calls.
Benefits Premium Healthcare
100% contribution to top-tier health, dental, and vision
Fertility Benefits & Family Building Support
Unlimited PTO
Flexibility to take the time off, recharge, and perform
Daily Lunches, Dinners & Snacks
We work together, and enjoy meals together too
SF, NYC, Dallas-Fort Worth, Chicago & 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
How we workShepherd 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.
Benefits Premium Healthcare100% contribution to health, dental, and vision
🥕
Fertility benefits and family building support Flexible PTOFlexibility to take the time off, recharge, and perform
🥗 Daily lunches, dinners, and snacksWe work together, and enjoy meals together too
SF, NYC, Dallas-Fort Worth, Chicago and LA Offices Professional DevelopmentAccess to premium coaching, including leadership development
Competitive 401(k) Plan Dog-friendly officePlenty of dogs to play with and make friends with in the SF office
