Head of Finance

As Head of Finance, you will own Shepherd's financial planning, accounting, controls, and reporting, as well as 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, report to the CEO, and partner with our Reinsurance and Capital Strategy leader as we add risk-bearing capacity. This is a position based in our San Francisco office.

Responsibilities

Oversee the annual operating plan, long-range model, and monthly forecast and budget-versus-actuals reviews across revenue, headcount, OpEx, and cash; Develop and improve 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; Partner with the Chief Insurance Officer and Reinsurance and Capital Strategy leader on the finance side of new risk-bearing structures, including 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 carrier partners; Oversee close, audit, tax, and spend controls, and manage the outsourced accounting partner; 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; Manage the Finance Lead and the Revenue Operations, Business Operations, and Analytics teams; Report to the CEO

Requirements

12+ 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, including 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; 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; 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

Nice to have

Fundraising experience; CPA, CFA, or MBA

Benefits

100% contribution to health, dental, and vision; Fertility benefits and family building support; Flexible PTO; Daily lunches, dinners, and snacks; Professional Development with access to premium coaching, including leadership development; Competitive 401(k) Plan; Dog-friendly office